8 tips for developing personal style when you have none

Guest post by Jackie

It's amazing how a cute dress, colored tights, and fun accessories can go a LONG way.
It’s amazing how a cute dress, colored tights, and fun accessories can go a LONG way. (Outfit from ModCloth.)
I have never considered myself “fashionable.” Growing up, I had the tomboy thing down and wore jeans and t-shirts through high school. And then college. And grad school too. At a tech school, the girls who put in effort to look nice stood out (and had to deal with occasional backlash), but always seemed cool and confident to me. Every so often I would get the urge to “dress cuter” and swear not to acquire any more free unisex t-shirts, and wear a skirt here and there. But inevitably I ran out of outfits to wear and reverted back to the same jeans-and-t-shirt look, not because it was more “me” but out of habit and because it was easy.

Then, I decided this was the year that I would finally dress the way I really want to, as part of my quest to figure out what being an adult really means to me. After a few months of going through my closet, lots of online searching, and one exhausting trip to the mall, I am starting to get a wardrobe I really like and figured I could share some tips for those of you who also didn’t just figure this stuff out at puberty.

Do some research

Like any good nerd, I started by reading as much as I could. Fashion blogs and Pinterest are a good place to figure out what styles you like, and just plain get exposure to new ideas. I also checked out a few books from the library about style and fashion, with plenty of pictures. Most of what I learned from there is what might work best with my body type, what the basics were, and how to mix up basics with the right add-ons to create something new.

Go through your closet

I had a couple drawers stuffed with the aforementioned unisex t-shirts. I kept my favorites for sleeping, lounging, and exercising in; then donated the rest. I now have a lot more space for new stuff, everything is easier to find, and I also dug up some nice things I had forgotten about because they had been buried. If you have things you never wear, that don’t fit, or that just plain don’t make you feel good, swap/sell/donate/toss!

Get basics, in multiples

I’ve been having a lot of fun looking at things like dresses and shoes, but most of what I wear is still based on jeans and a t-shirt. However, now I’ll go for something like a women’s cut V-neck that flatters me, and get it in several different bright colors. Jeans are really difficult for me, so when I find a pair that actually fits, I’ll get more than one. If you’re shopping and happen to find something basic that you plan to wear a lot and fits you perfectly, I would highly recommend getting several at once if you can.

Accessories are your friend

And, sometimes the cheapest and quickest way to change up your outfit. If I swap my Converse for a nice pair of flats, my backpack for a more structured cross-body purse, and throw on a scarf, boom: instant grownup! And definitely think outside the box. I’ve been trying colored tights while it’s still cooler out to make a plain black skirt or dress look spiffy. I’ve heard statement necklaces are a thing now, too.

Get a few bolder pieces

I needed a jacket to replace the tattered hoodies I wear during those in-between seasons, so on a whim I ordered a cropped red faux-leather jacket online and I love it! It’s louder than what I would normally have picked before, but now I wear it just about every day, weather permitting. I also treated myself to a fun pair of shoes that I wear when I want to step it up a bit. If you can afford it, taking risks on one or two louder things is a good way to evolve your look without a complete wardrobe overhaul.

Understand the trade-off between quality and price

In grad school, I got a cheap pair of boots in the fall and wore them just about every day. By the new year, however, they were all scratched up and the soles had collapsed into a soggy mess after a really rainy night out, and now they just sit in my closet. So, after graduation, I treated myself to a nice pair of brown boots that cost over three times as much. I still wear them all the time, and though they’re scuffed, they are even more comfortable than ever and still look cool (plus, they’re waterproof). By the time they break down, I will have paid pennies for each wear I got out of them. On the other hand, those “riskier” items I mentioned above? I went cheap. A good rule of thumb is to be cheap with trendier things, and go for the best quality you can afford on things you know you’ll wear all the time.

Don’t be afraid to go online

I don’t know about you, but shopping in a mall is completely exhausting and frustrating. It’s still useful for certain things like finding those perfect-fit basics, but I’ve actually had much better luck online. Many places now offer free shipping and returns, and being able to read reviews (particularly about sizing) and see what other people wear it with has been awesome. So far, my favorite places have been ModCloth and Zappos, though there is tons out there.

Break your own rules!

Finally, this one has been both the trickiest, and the most important for me. I had to realize that I had been holding on to weird internalized rules that I had developed when I was growing up. After the “popular” girls rejected me in elementary school, I had fashioned an identity out of being a tomboy, and not concerning myself with any of that silly “girly” stuff later. So, I didn’t wear makeup, I never wore anything other than sneakers, and I hardly ever wore skirts and dresses unless there was some special event. Going to a tech school for college also didn’t help, as girls who took the time to look nicer also had to spend a lot more time proving themselves, amid subtle messages that feminine = inferior. All of that added up to me sticking to my same safe formula, and a growing sense of dissatisfaction with the way I presented myself to the world. So, it’s really worth examining what reasons you have for dressing how you do now, if it’s anything other than “it makes me feel good.”

Breaking out of my style rut has been an interesting experience, and a few months after I started I now feel happier about how I look and feel more confident when I go out. It will always be a work in progress, but my clothes are starting to reflect something that feels more “me” overall, everyone else be damned. Hopefully, if you’ve been feeling stuck too, some of these tips can help you out; and if you have your own, or any thoughts on personal style, I’d love to hear them!

Comments on 8 tips for developing personal style when you have none

  1. I also am very much a jeans-and-t-shirt kind of person, and I feel like my biggest problem is getting what I like to actually look good on me. I’ll take inspiration from a really cute outfit I see somewhere and try the same basic idea, but it just winds up looking like crap. I think there’s a disconnect between the fashion part of my brain and the part that makes things actually happen πŸ˜›

    • Aww, don’t be so hard on yourself! What actually really helped me figure out what might look good was watching “What Not to Wear” on TLC. It’s kind of cheesy reality TV, but they really do help people dress better for their body type, which makes them feel more confident, which makes them look even better. They also have a book out called Dress Your Best, which is one of the ones I borrowed from the library when I started. It has tips for a whole lot of different body types.

      Color can also have a huge effect on how you look. For example, I glow when I wear orange and red and other warm earth tones, but look like death in pastels. It may be worth looking into color seasons if you feel washed out by your clothes.

      Finally, sometimes it really is the details that make it. I have plenty of outfits that look really boring until I add a scarf or a necklace or something.

      • I cannot recommend What Not to Wear enough. I’m a nerd raised by a hippie, and I was homeschooled. Fashion is not something that comes naturally to me at all. What Not to Wear showed me that fashion is a skill I can learn just like algebra, video editing, home repair, or anything else.

        • That’s a great way to think about it! So some people I know are just naturally gifted at putting an outfit together, but there’s no shame in my having to give it a little more thought and practice.

        • It is a skill. I hadn’t thought about it like that, but it took me reading magazines for years and then getting some friends into fashion for me to look at things differently. I think most of us have the ‘get basics in multiples’ down, it’s the bolder pieces that we don’t focus on. Also, try clothes on even if they might look weird on the hanger; it will hang differently on your body.

        • The problem I find with those shows, for someone with my shape it is dresses, with belts to show off your waist and heels. I skateboard, kiteboard, rdide, run up all staircases. You can’t do that in a dress.

          • what about Skorts? Like from Title nine or Athleta. I love mine. I get a skirt, but if I need to crawl around on the floor with the toddler, I’m still covered.

          • I do many rediculous things in dresses/skirts…. full skirts for free movement and leggings cut off at the knee is my prefered trick for modesty. But that’s me πŸ™‚

            And screw heels…

        • I just wrote a whole post about WNTW below. Everything I ever learned about fashion, I learned from Stacey and Clinton. The show is a little lame, but also like an instruction manual for learning to dress.

          I even have my own set of “rules” for myself that I use whenever I go shopping.

      • Heh, that show has slowly been inspiring me to dress better too! Though I’m not sure they’ll ever quite get me out of jeans. On the other hand, there’s really no situation I’m in on a regular basis where they’re inappropriate.

        • Well, I think Stacy and Clinton would be fine with that; their biggest pet peeve seems to be when people are wearing jeans that don’t fit them. πŸ˜› I wear jeans about 6 days out of the week myself.

      • I am a total WNTW follower. I am someone who my friends ask for me to go shopping with, and I find myself repeating to my friends, “Color, pattern, texture, shine! You can do it!” Love them so hard.

      • The thing I really dislike about that show is that they make the person get rid of their entire wardrobe before showing them what they should be wearing. With how much I dislike shopping and how difficult it is to find things that fit, I’d never allow someone to get rid of my current wardrobe. Also, the way they often humiliate the person they are trying to “help” isn’t cool, in my opinion. Then again, I’ve only ever watched the show briefly, so I might have gotten the wrong idea about it.

      • The trick that What Not To Wear doesn’t mention is that all those amazing off the rack clothes that look amazing at the reveal is that ALL of those outfits are tailored off camera.

        It’s amazing what knowing a good tailor and buying clothes one size up can do for you.

        • I did not know this and it changes my perspective on the show soooo much, I also prefer the original british version with Trinny and Susannah.

          I buy all my jeans one size up, on sale then have them tailored they fit great πŸ™‚

          • thanks for this tip!!! I can never get pants that fit well – too tight or too loose. Now I know the secret!!!!

        • They do mention the tailoring on the show (or they did back when I watched it). They say to get something to fit the biggest part of you and then tailor down. Since having a baby and recovering from being sick, I’m going to have to rebuild my wardrobe from scratch and am planning to get a good tailor to help make sure things fit better.

    • I’m with Jackie – don’t be so hard on yourself! Getting it “right” is always a moving target. I would add to the other comments here that a good tailor goes a REALLY long way. Sometimes we all need a little fabric let out, tucked in, or otherwise maneuvered to look really fabulous. Spending an additional $10-30 per piece may seem like a lot, but finding ready-to-wear items that automatically fit is something like finding the fashion unicorn. Good luck!

  2. I love this. You and I are from similar molds. After college I started to slowly acquire big-girl professional clothing but now post-baby I have reverted back to my comfort clothes to ease my self-confidence. I wish that I could win one of those wardrobe make-over prize packs because going slowly is time consuming, stressful and expensive. Why can’t the world just accept jeans and a hoodie?! πŸ™‚

    • I know what you mean about wanting a wardrobe make-over prize pack! What’s helped me is tweaking my monthly budget to set aside a fixed amount I can spend on clothes/shoes/etc. every month, for about six months or so. I know it’s not totally feasible for everyone, but a bit at a time is how I built up my t-shirt and jeans wardrobe in the first place, so it’ll take a little while, and conscious effort, to evolve it in a new direction. A big initial step was stopping the inflow of all those t-shirts! (Seriously, where did they all come from?!)

    • Can I suggest op-shops? Or whatever you call second hand shops?

      Because there’s such a variety of clothes and it’s all cheap, it can give you a feel for what looks ok/good at a very reasonable price.

      For the recent big school holidays, I completely redid my professional (school teacher) wardrobe for $100 and something like 10 different op-shops!!

    • start with your jeans and add a scarf or piece of jewellery. It’s amazing how shoes can make an outfit look so different. Instead of sneakers, pop on a pair of ballet flats or heels – or boots. It will change the look dramatically. Then buy some new tops – one at a time if that’ s all you can afford. As someone suggested, op shops (charity shops) have some great finds. But scarves are a great way to add pizzazz to an outfit for very little outlay…….

  3. I am going through a somewhat similar process. Makeup and girly stuff have never been my thing and going to college/grad school in a STEM field did help. Now I am out the the grown up world and I need to dress professionally. I have not figured out my style yet. I like comfortable and colorful, but my workplace calls for dressy and muted colors (black, grey etc). Also, there is this huge psychological barrier in my brain that prevents me from looking at fashion/girly things (ack, not for people like me, what am I doing here…) Anywho, inspiring to read about your journey. Now I am off to pinterest to look at pictures of what I might like (although not convinced yet that it might actually be fun ;)).

    • I absolutely feel you about not thinking the fashion-y stuff is for you. It’s really hard to tease out if it’s actually because you don’t like it, or because you don’t think you should like it. There’s a wide world of fashion out there, so I hope you can find something that you might like. My trick is to find people on Pinterest who have similar tastes and just follow them, and they do all the work for me! πŸ˜› Another recommendation I can give you is a book like this–sometimes it just helps to have a name for what you’re looking for! I would say my style is “colorful nerd with a rock twist.” Though that’s not in the book, it was a good jumping off point for me about different kinds of styles.

      As far as workplace clothing, the upshot of being an engineer is being able to pretty much wear what I want. Which used to mean the same student wardrobe, but I’m working on the courage to get more experimental. I still definitely save the more colorful/revealing things for weekends and going out, though.

    • You can usually get away with adding a “pop of colour” to an otherwise muted outfit without violating the dressy/muted rule. Something like vibrant socks, scarves, or other accessories lets a little “you” shine through the muted corporate grey.

      • “pop of colour”

        This, this, this! I’m just starting to understand the power of accessories. Much of my wardrobe is black and grey (and safe and boring), but add a bright scarf, green bracelet, yellow shoes, or my red coat and suddenly it’s interesting!

  4. STORY OF MY LIFE!!!!!
    Up until college I wore huge baggy shirts and huge baggy pants (made me look super tiny being a tiny girl to begin with…)

    I wish steampunk fashion was socially acceptable – then i might not have a problem filling my closet with ton’s of clothes!

    • I actually knew a girl in college who pretty much always dressed like an anime character–a mix of steampunk and Japanese Lolita? It was awesome, and she was super confident!

      You should pick a day where you just go out and do all your errands dressed totally steampunk. And then tell us how it went.

    • You know, there’s a community on livejournal called steamfashion and sometimes people post “this is my steam-influenced but still normal-ish looking outfit” things.

      Also, the base clothing for steampunk isn’t too far out there right now. Things like tiered skirts, or skinny tousers tucked into equestrian style boots, subtly ruffled blouses and buttoned vests and cool belts are fairly normal. And also steamy.

      Often, the thing that holds people back from dressing how they really want to is a fear of being overdressed, or feeling like they’re wearing a costume, because it’s so far from what they normally wear. I mean, if you’re normally wearing jeans and t-shirt, a button up and trousers is gonna feel like you’re being fancy. The trick is to take “normal” and bump it up a few notches. If you wear nicer clothes every day, that just becomes your normal.

      ….Can you tell I like clothes? I REALLY like clothes.

      • Urgh, yeah, being worried about being overdressed! I also had a weird thing about how my mom and grandma would have loved me to dress up more and wear makeup while growing up, which made me dig my heels in harder (naturally).

        Still trying to re-calibrate my normal. So far I’ve worn a dress or skirt to work a couple times, after much deliberation, and no one seems to have noticed, which in this case is good!

        • But that is my biggest problem – apparently it IS very obvious to my coworkers when I wear a dress, or try to dress up a little more than I normally do. Apparently I am so ingrained in my pants/cami/cardigan “style” that trying to look a little cute every now and then is entirely noticeable, and I don’t think I can stand it if people say, “Huh, you look nice today!” in such a way that implies that it’s surprising. Sigh. And I don’t have enough in my wardrobe to keep it up consistently, so they would never get used to it. Argh.

          • It’s funny, the day after I wrote that comment I wore a casual-but-nice dress to work and someone asked me why I was dressed up! The environment where I work is pretty informal, though, so I told him I wasn’t and it was basically a way for me to get away with not wearing pants to work, which he thought was funny.

            It’s definitely a slow process to change your style–I’ve been consciously working at it for months and still revert back to older habits maybe half the time. I’d say keep mixing a couple cuter things into your normal rotation as much as you can, and people will probably stop commenting on them. Maybe mix up your more “normal” outfits too, like adding a necklace or wearing a low-key skirt instead of pants? If you have a friend who is good at that, maybe he or she can take a look at your closet and come up with combinations you hadn’t thought of before.

      • I agree with this. I love the steampunk aesthetic, but will never go all out in an outfit. I like wearing “steamy” influenced clothing. Like pairing a modern pencil skirt with a ruffled blouse (I love ruffled blouses!!).

        You could also pair a tiered skirt with a simple singlet or tee. If you love steampunk clothing, but don’t want to be “dressed up”, then choose one steampunk item and then dress it down. Blouse + jeans, skirt + tee, jeans + simple shirt + vest/corset/cincher, etc. Blend with modern clothing so it’s not “out there” but more like an accessory.

  5. A helpful tip when doing research: take full-length photos of yourself in the outfits you have. Try and take them from the side, front, and back. It’ll give you a more objective idea of how something looks on you, if the colors are right, etc. It’s hard when you’re shopping, but if you’re at a store with a good return policy it might be worth buying it, photographing yourself, and then deciding if you want to keep it.

    edit: I thought about this and realized that sometimes people like to wear something because they like it- not because it’s “right” for them. Which is cool! Just a tip for those who are thinking in terms of body types.

    • Also keep in mind you might tend to be way harder on yourself than on other people, or harder than other people might be on you! That’s where having a gentle but honest shopping buddy really helps (especially if s/he finds something for you that you wouldn’t think of). Or, if you can manage to distance yourself from the picture, what would you think if you saw a friend wearing that, or someone on the street who looked like that?

      • Gentle but honest shopping buddies FTW! Someone who knows you and knows clothes, and knows how to say, “It’s a beautiful piece of clothing, but I don’t think it does you justice. Let’s keep looking!”

      • Hmm, maybe I’ll make another post about that then, once I can come up with an interesting angle. I would love to read about other people’s interesting jobs too. Maybe an Offbeat Career series on OBH/L?

        • I’m actually really curious – what’s you’re main focus in mechatronics? Electrical, computer, mechanical, etc?

          I ask as I’m trying to get into robotics (currently a grad student) but as a mechanical engineer feel like I have so much to catch up on because I only know a bit of AI and computer stuff and very minimal electrical stuff.

          • Woo robotics! My focus right now is actually everything, since I work as a consultant. Lately it’s been a lot of coding, with some mechanical design/fabrication and wiring thrown in. Electrical is certainly my weakest point too, but I happen to live with four EE people, two of whom are getting PhD’s in analog circuits.

            My degrees say mechanical, but I actually switched over from EECS in my junior year and managed to get away with doing a sort of hybrid course of study before I even knew mechatronics was a word. I think I just like too many things, but now it’s really useful for my job!

          • *butting in* Robotics you say? I mentor a high school FIRST robotics team (And I’m so not even close to an engineer) but its super rewarding to see what these kids can do. And I know teams are ALWAYS looking for adult mentors – and working with other engineers will help you boost your skills too.

            The web site is usfirst.org and if you click on FRC (high school) and then go to ‘find a team or event in my area’ you should be able to find something. The season is winding down now (build is january – mid feb, and competition runs from March to end of April) but jumping in with a team on the off season might be an ok thing. πŸ™‚

  6. Interesting, and I think this can go the opposite way too. I spent most of my late teens/early 20s intentionally cultivating a fairly “adult” style, which was exacerbated by my move to a large city whose wealthy class I sought to emulate. It wasn’t until recently I’ve felt comfortable saying “fuck you” to a consumer culture I never believed in, and started dressing in a way I’m much more comfortable (I’d describe it somewhat self-deprecatingly as “heavy metal dirtbag”). While it might not be the most grown-up seeming appearance, I’m no longer wracked with anxiety over the cost of maintaining a yaletown-approved wardrobe, nor over my lack of perfect body/skin/hair to go with it. Personal style is just that–a style that makes you personally feel awesome!

    • I love this! (And your description of your current style–it’s helped me to try to find a description of what I was aiming for; so far mine is “colorful nerd with a rock and roll twist.”) Sounds like we had both put ourselves in boxes we didn’t really like. Glad you feel more like you now!

  7. I finally started doing this during this past year. I’ve been re-inventing myself through my clothes and I’m much more confident in my own style in my 30s that I was in my 20s.

  8. I very much believe in “dress for the job you want, not the job you have”, and I’ve been wanting to look more like a grownup. I’ll go out and buy some accessories and nice shoes, but it never lasts more than a week. Bracelets, earrings and necklaces always end up snagging on my hair, and I take them off after a few hours. My arches begin to ache in flats or pumps, and after a day it’s back to my sneakers. Blazers and button downs just don’t come in my bust size – there’s always tailoring, but now you’re talking about a level of effort that exceeds my interest. A college friend once told me, “beauty hurts, baby”. Well screw that, I’ll stick with the sneakers and tshirts.

    • Totally unsolicited and possibly unwarranted advice:

      1. If your shoes hurt, they’re the wrong shoes. There are nice, stylish shoes that don’t make you want to murder people. I like Clarks. Some of their stuff is cute, and SO COMFY. I have weird feet, and the right Clarks don’t hurt. Also, inserts are your friend.

      2. I, at a 12 inch difference between bust and waist, also have problems with shirts. Draped jersey shirts want to be your work-appropriate, grown-up friend. They will love your boobage and not pop open at inopportune moments.

      3. It is often worth it to find just one blazer or jacket and get it tailored. You really only need one.

    • I completely understand the button down shirt problem. I am not crazy busty, but I am not flat either. I also have broad ass shoulders from swimming. In order for my boobs and shoulders to fit into a shirt it I have to always go for at least a large if not XL. Then I can wind up feeling like I am swimming in the shirt because it doesn’t give me any waist.

      I am also struggling with trying to add to my wardrobe because I keep thinking maybe I finally start losing weight. It’s more of a I know if I try to buy more clothing my current size, I will wind up losing like 15 lbs and nothing will fit again.

      • Elasticated belt around the waist sometimes solves that provided the shirt doesn’t get vertical creases too badly. If you know a crafty person they might be able to put darts in a shirt for you to tailor it.

    • just a quick comment here about arch support – those Dr Scholl machines, that you stand on and it reads your feet and recommends one of their products? they are MAGIC. my husband had custom orthotics and didn’t love them. he decided to give this a whirl and LOVES them. 2 pairs for about $60. They’ve lasted over a year so far. And are easy to move from shoe to shoe. I know I sound like an informercial, but, if you have sore feet all the time, it can’t hurt to try. (do the machine three times – make sure you get a consistent reading.)

      • Oh and you don’t even need the Dr. Scholls version. I need the arch support and Dr Scholls would charge like $30 what the other brand is only $8 and honestly have much stronger support so this is more of a do their machines and look at ALL the inserts in the store that help with support there if you need to save money.

    • I feel you, I totally do. For pretty much the same reasons. If it takes much time or isn’t comfortable it ain’t happening. For me the trick was to step a little outside of the narrow box of what is appropriate. Think oxfords or chunky low heeled leather boots. I second the comment below, drapey jersey shirts are a win for the boobs and can make you look slim below.And maybe try adding sweaters over a clean plain fitted t-shirt and slacks. Lots of nice sweaters these days from super drapey layered open front cardigans to button or zippered front more form fitting stuff. The latter can be surprisingly more forgiving than a button down or blazer because they’re soft and stretchy.

    • I hate wearing necklaces for that very reason. Also, I wear a key chain around my neck at work, and a microphone. I don’t need anything else around my neck, thank you!!

      But I looooove brooches. My favourite etsy stores* for handmade wooden brooches are:

      Nothing dangling off my wrist to clink on the desk while typing, nothing to get caught up in my key chain/microphone/hair and nothing to make my ears itchy. But still pretty!! Yay! πŸ™‚
      /suggestion for jewellery.

      *I haven’t been paid to promote any of these stores. Nor do I own any of these stores. But I have bought from (most of) them and wear those brooches proudly.

      • I really want to get into brooches – I think they look so cool and so personal! – but I never know where to put them. On my coat? On my shirt? But then does my shirt get pulled down by them?

        • Well, that depends on the weight and size of your broach and the material of your clothing. The thicker and/or stronger the fabric, the larger and heavier a broach it can support. For example, a large metal broach that looks great on a heavy wool coat would hang terribly on a tee shirt, and possibly even damage the cloth.

          You don’t need to only put broaches on shirts, either. You can pretty much use broaches on any fabric you can get the pin through. Just be careful the pinhole won’t end up permanent, such as with leather.

  9. I think all of us engineering school grads wound up in the same basket on this one. I still cannot wrap my mind around proper office attire (without resorting to polo shirts and khakis like the guys around me), and my sense of personal style is stuck somewhere back in the punk-goth persona that I identified as in high school. Toss in some not-so-great body image issues, and fashion might as well be Everest.

    Since I work from home (yay freelance!), I can afford to hang around in jeans, woot! shirt T-shirts, or fluffy peasant skirts. My problem is that I just don’t feel up to par with the boy, our group of friends, and the adult world when I step outside of my home office. Taking that step and working on a personal style is something I feel I should do…but I have absolutely no idea where to start. Your post actually helped with that a little (giving me a direction to begin researching in, for one), so thank you so much πŸ™‚

    • Wow, you are basically me. In every point you made. Not really sure what my personal style is, body image issues, jeans, tons of woot! tshirts and fluffy peasant skirts… no idea where to start… Good luck! I just want something that is comfortable physically and confident mentally.

  10. I tend to wear my clothes more if a friend or my husband picks them out for me because they see me much better than I see myself. If I shop alone, I end up feeling stupid because nothing seems right. Being short and fat just doesn’t help. And here comes summer, and heat, and……*sigh* more jeans.

    I do love me some earrings and necklaces and scarves though. I have tons of those. And insanely funky socks.

    • i’m totally incapable of clothes shopping without my wife. come to think of it, i pick out most of her clothes, though. i think it’s something about “outside perspective” both visually and emotionally.

      plus, if your partner thinks it looks good on you, well, mission accomplished =)

      • I can very easily pick out clothes that I know my husband will love, but for me it’s completely different. The style of clothes that I love just doesn’t mesh well with what I look good in.

        And you are absolutely right. If my guy thinks I look sexy in it, mission accomplished indeed! πŸ™‚

    • I actually feel more comfortable in a jersey or cotton material just below the knee length skirt than jeans. It’s hard for us short people to pull off the long maxi skirts, but I think skirts are more forgiving than jeans. Especially if they have a little ruffle. And casual skirts can still be paired with tshirts or short sleeve button downs!

  11. I’m kind of slowly going through this phase, too. I am also another tee-shirt and jeans girl. Partly because I ride a scooter all the time, and tees fit under armored jackets well, and jeans are obviously decent riding clothes (I personally can’t do armored pants). Generally, the first thing I do with any new clothing that catches my eye is ask myself if I can wear it on the scooter. If I can’t, I’m highly unlikely to get it (though this applies to shoes more than other clothing). I felt like I was really breaking out of the box the other day when I picked up a few skorts on sale. I’m even wearing a cute pair of oxfords more often now as opposed to sneakers. I guess we’ll see if it goes anywhere from here…

    • Oxfords and skorts sound really cool! For a while it just plain didn’t occur to me to wear non-sneaker shoes–I assumed if they were cute, they would hurt. I am now all about the flats.

      My limiting factor for work days is “can I wear it on my bike without flashing everyone.” I’ll have to figure out a solution to that soon since summer is coming and I want to wear more skirts and dresses…hmm.

      • Skirts on a bike are doable, you just need to pick your skirts carefully, and/or be willing to wear bike shorts or something under them while you’re in transit. I have one twirly knee-length skirt that I wear on my bicycle all the time β€” the fabric is heavy enough that it doesn’t have a huge problem with wind (although ΓΌber-windy days still sometimes pose an issue…), and it’s short enough that it doesn’t get tangled in things.

      • When I was still in school, bicycle or similar shorts were basically a personal requirement if I ever wore a skirt shorter than my knees. It’s easier to find uber-thin dress shorts these days, and some even have cute lace on the bottoms. Kind of like the modern version of ladies’ bloomers. Obviously that won’t work for a mini skirt, but it should for just about everything longer. And hey, you don’t have to wear a slip if you get shorts that kind of match the skirt.

        I’d like to be able to wear skirts on my scooter. But I have one that goes fast enough, no amount of heavy fabric would escape being blown around too much. And anything that’s skinny enough not to fly up is too skinny for me to safely put my legs down to hold the scoot up at a stop. I have been known to bring a change of clothes with me if I’m going somewhere I really shouldn’t wear my “safe riding” clothes to.

  12. I know this seems simple, but look around at what people are wearing wherever you go. When you find yourself thinking “she looks cute, nice, professional, etc,” make a mental note of what she is wearing. This is especially helpful if you notice someone with a similar body type!

    Even subtle changes like wearing dark sneakers instead of dirty white ones and a sweater instead of a sweatshirt can make a big difference in your appearance. And I was shocked to discover that sweaters now are not the itchy terribad sweaters of my youth!

    Sizing is also important. I don’t like wearing tight clothes. They call attention to the bulges, and they just aren’t comfortable for me. But clothes that are too big also add bulk! So I try to go with the size that skims my body without clinging to it.

    Also, if a style makes a model look awkward, you know it probably know it won’t work on you (a normal person) either. Sometimes certain styles just don’t work with your body type, so wait until next season for the new styles! (I’m talking to you, high/low shirts and skirts!)

    • My non-work attire has become basically an adult version of my jeans/hoodie/chucks or vans routine of high school and college.

      jeans–> dark and fitted
      hoodie–> fitted T shirt and cardigan, they don’t even really have to match
      chucks–> rubber soled leather flats (usually naturalizer, clarks, or born)

      This kind of routine requires no more thought or effort than the hoodie and is every bit as comfortable but looks much more polished. All I have to do is throw on a scarf or a big piece of jewelry and I can go out to dinner or whatever.

  13. Gawd, this post is awesome. I am the WORST at dressing myself. My fashion skills are about on par with my cooking sills. This is making me wonder if, much like the cooking challenge, should do a fashion challenge one of these weeks where I’m not allowed to wear my work-at-home uniform of pj pants and a tank with a built-in shelf bra?

    Ha. Oh fashion, how I appreciate you from afar.

  14. This is a well timed post for me! I’ve been filling bags with my clothes to be donated, leaving me with very little. I’m happy getting by with my “uniforms” for now as it’s finally giving me time to look for things I REALLY want to wear.

  15. I am still working on this… I have a love/hate relationship with fashion. I LOVE to look at it, a lot, but when it comes to wearing it—not so much. You’ll find me in jeans, Chucks, and a simple top pretty much every day. The ‘My Style’ Pinterest board contains dresses, cute heels, and other awesome things but in reality that just doesn’t work for the majority of my life. I have one job where I have a uniform, plus I am an artist so anything that I wear has the potential to be completely destroyed by clay or paint. When I am not doing one of those two things I’m working on the house or chasing my very, very exuberant toddler. AND being plus size? Damn, I know the fashion has come a long way but all the cool stuff I like is crazy expensive!!

    I guess one day I’ll get it. I just have to take baby steps πŸ™‚

    • You and I need to hang out together. You just described me down to the size. I’m almost to the point where I want to learn how to make my own clothes! I pin a lot of outfits that are adorable but I doubt they would look great on me in reality.

  16. I have a wardrobe full of corporate outfits that I wear at work to project an aura of credibility and professionalism, but I’m really stuck as to what my “personal” style is in my spare time. I either have farm/home clothes, corporate clothes, and nothing in between to wear to a cafe or the movies. I just don’t know what I want my casual clothes to say about me, and it’s not what it was when I was in uni anymore. I like your tips, especially the one about breaking your own rules and being brave about what you wear.

    In New Zealand we are heading towards winter, and I’m really stuck for how to look stylish and be warm and cosy at the same time. Either the clothes in the high street shops are too flimsy, or the warm woolly clothes are a little too close to what my Mum and Gran wear!

    • I’m with you on winter clothes. Tights, boots, layers? If you want to be daring, maybe a brightly-colored, well-fitting coat. It’s only risky half the time, since you take it off when you go inside!

    • I know this is a fashion-101 type tip, so maybe you’re already up on this… but somehow it never clicked in with me until last November/December: SCARVES. Tossing a scarf on with my general t-shirt and jeans uniform made it look so much more put-together this winter. I got them from this woman on etsy (https://www.etsy.com/shop/ModLux?ref=pr_shop_more – I don’t have any affiliation with them whatsoever, but I love her grey chevron infinity scarf!), and they’ve made me feel so much more adult this past winter.

      • Yes, they help so much! A black/grey/brown one can tone down a bright shirt. And a bright, textured, fun one can brighten a neutral outfit! Also they stop me from reaching for my hoodie in winter, when I know I can wear a funky v-neck shirt and still stay warm in the office with a scarf.

        For summer, there are lots of breezy lightweight scarves that are great for over sundresses when you go in the air conditioning. Scarves are great year-round!

      • YES, YES, YES!!! Scarves are the best! I probably have 20 or more of them. I’m pretty conservative in the way I dress (mostly solids, lots of black, gray, white, and brown, no ruffles or lace), so most of my outfits are pretty boring, but I go NUTS with scarves. Even a plain white button down and black slacks look great with a gorgeous scarf!

    • Layers are your friend! I wear a lot of long skirts in the winter, and I’ve found that I can hide a lot of extra skirts under a long flowy skirt! Also, for non-frumpy but warm & wooly, I’d recommend Ice Breaker whole-heartedly. I love their stuff! (And they’re even New Zealand-based, so you can feel good about shopping locally. Unlike me. I live in Canada, and buy New Zealand wool.)

    • absolute staples for a good Kiwi winter, in my opinion: 1. at least one really nice long sleeved merino top, preferably in a colour other than black – it doesn’t matter whether you pair it with jeans or a skirt, a nice bright jewel tone or colour that makes you happy will make the outfit look much more “purposeful” than (cough my own default) black all the things.
      2. a really nice, good quality pair of boots; I love calf length boots because I have trouble fitting knee high ones, but find a pair with a low heel or that are flat and again, you can wear them with a skirt and tights or jeans!
      3. if you’re a skirt person, wool tights. All of them. I always found the best range at Farmers, but from personal experience the cotton ones are usually rubbish – wool and nylon mix will keep you warm and not sag as much!

      I really like what you say about not knowing what you want your clothes to say about you; this has been the spur to several wardrobe overhauls for myself. I’ve found that if I go towards things I like and feel comfortable and confident in, a style will develop around that. I’ll pick up a couple of pieces I like and work from there – what do I like to wear them with? what kinds of ways are other people wearing these that I might not have thought of/think looks cool?
      and wow that was a really long comment I’m sorry I have a lot of feelings about clothes and being warm in winter!!!

    • Zappos- free shipping

      Amazon- free shipping on some things

      Athleta- free ship over $49 and free returns and exchanges if you call and talk to them and not do it over the internet, plus a lifetime guarantee (I’ve returned things over a year old if they aren’t worn)

      Sahalie not free shipping or returns, but a lifetime guarantee (I’ve returned items worn and hemmed when they still weren’t what I really wanted)

      Title Nine- Lifetime guarantee

      LL Bean- Lifetime guarantee

      Save your reciepts!!

      • Yup–Zappos has free shipping, and free returns. A lot of places will let you print out a label online and then you just drop it off at a UPS store without paying anything.

        Many, many other places offer free shipping if you reach a particular minimum amount. For example, at Modcloth it’s $50.

        I’m in the US, though, so it may be different for other countries.

      • Icebreaker has something like a 1-year guarantee, too! They make wonderful merino wool clothes, which I wear basically constantly, and when I wore out the elbows on the sweater I got from them (less than a year after I got it), they sent me a new one free of charge!

    • Nordstrom and right now Macy’s do too.

      Sometimes Ann Taylor and Loft do when they’re having a promotion.

      For cheaper stuff, Old Navy. Even if shipping isn’t free, you can return/exchange at the store what doesn’t work from your online order (and you can do so at almost any brick and mortar store from it’s online counterpart).

  17. I love this post! I’ve been slowly trying to upgrade my own wardrobe. I think my biggest problem is that there’s plenty of things that look good in a store, but just leave me feeling awkward in public. Like shirts that are just a bit to low cut or just don’t go with anything I own. I should probably go back through my drawers and remove things a little more harshly.

    Goal 2 is new shoes and boots, so I stop wearing a half-destroyed pair of boots all winter, and a pair of black and pink runners all summer. Trying to find shoes I can wear for more than 3 hours is hard though.

    • Every so often Target or some other store will have a sale on “long and lean” tanks, which is a stupid name, but they are great because they can be worn under shirts that are too low cut or not long enough.

      And even though I am in NO way conservative or modest, there are a few websites that have really cute ideas to refashion a top so the goods don’t spill out…things like adding fabric panels and such. I’m sure if you google “modest is hottest” you can probably find them.

      Also, scarves help with covering up a too low-cut shirt. And easily removable, haha.

  18. I’m trying to figure out where my evolving sense of style (or lack thereof) is going right now. I’ve worn out a lot of clothes recently, so I’m trying to decide what to replace them with. I’ve been realizing I own a lot of black (three black skirts, three plain black t-shirts, a black button-down shirt for choir performances, a black hoodie, and a black shawl…), so my current challenge is adding some colour back into the mix. I also just bought a couple pairs of jeans, since my previous only pair of jeans had holes in it.

    What I wear has changed a bunch over the years, generally for comfort or practicality. I grew up in sweatpants & turtlenecks handed down from our (wheelchair bound) neighbour across the street, then eventually switched to t-shirts and jeans, which I wore for many years (probably from sometime in elementary school-ish to sometime in highschool-ish, but I’m not really sure, since I was homeschooled…).

    Sometime towards the end of highschool-ish, I started going to a lot of contra dances with my best friend. Contra involves a lot of twirling, so it’s way more fun in a skirt. (At dance festivals, a lot of the guys also wear skirts!). I usually borrowed my friend’s skirts for the dances, and sometimes they came home with me and I wore them to school, and then I decided I really liked skirts, so I went to the thrift shop before I left for university, and I bought a bunch of skirts. I also have a lot of funky socks (knee-socks are my favourite), so skirts and knee-socks were my style through the first couple years of university β€” knee-length skirts in the summer, long skirts (with lots of other skirts under them for warmth) in the winter.

    Around third year, I started biking everywhere. Now most of my clothing basically has to be bicycle-compatible. Not so many long skirts, since they get caught in my chain, or tangled in my wheel. (I’ll wear them in winter when there’s salt on the roads, since I don’t have a winter bike, and I don’t want my bike to rust). I can still wear a few of my shorter skirts, though, so my current go-to outfit is a black knee-length skirt with black wool leggings, knee-high funky wool socks, and generally a wool top and wool hoodie I have. Wool is great for bicycling, in that it stays warm when wet, and doesn’t get smelly too fast. Unfortunately, it tends to be really expensive, so I wind up wearing the same clothes over and over again.

    I’m not entirely happy with my current look, and I’m not 100% sure why. I think maybe it’s a little on the unprofessional / student-y / not-yet-a-grown-up side, and since I’m now a part-time student, I don’t really want to look like a funky university student anymore… Maybe part of it is that I think I should have more of a sense of style, given I’m a graphic designer. Maybe part of it is that I can’t really afford to go out and get new clothes, and I generally hate shopping anyway, but that doesn’t really lead to me having a lot in my closet that I like, since I wear things I like obsessively until they wear out. I’m not exactly sure what I want to get, yet, although I know I want to buy at least one dress, since I like dresses, and the only one I currently own is my wedding dress.

  19. Thank you. I’ve struggled so much with developing a personal style. I feel like I have a few factors that make it difficult:
    1) having been pretty broke for a long time, and not having the money to buy new clothes. This would not be a problem if I knew how to shop at consignment stores. I do not, at all.
    2) I have no idea where to buy the few things I know I do like. For instance, I love twirly skirts: pleated skirts, circle skirts, patched skirts, gored skirts, broomstick skirts, I don’t care, I love full skirts. But where on earth do you get them? As a teen, my go to was asking my mom for them for my birthday from Sundance Catalog. Which is WAY out of my pricerange right now.
    3) I have NO IDEA what to do on top. Jeans and a t-shirt, I can do. But what do you put on top with a skirt? With different kinds of skirts? No idea at all.

    I really want to be more fashionable, but I struggle with it. Thanks for the kick in the pants to work on it more, and try to learn to thrift store shop.

    Updated: Wow, it put the link it itself. I wasn’t trying to promote Sundance, although I love their skirts, but the comment thing put the link in. Kinda amazed.

    • Twirly skirts are the best! As to what to wear with them, it does depend a lot on the skirt. If it’s a heavily patterned skirt, then you’re probably best with a solid colour (black goes with nearly everything, although if you can pick up a colour from the skirt’s pattern, so much the better), whereas if it’s a plain solid coloured skirt, you can wear a top with a little more pizazz. Some people can probably pull off patterns top and bottom; I’m not one of them. When I wear a skirt (which is most of the time), I tend to wear fitted Ts (short or long-sleeved, depending on the weather), tank-tops occasionally, and sweaters in cool weather. Depending on your personal style and the particular skirt, you could also wear a button-down shirt with a belt (wide and narrow belts both seem to be “in” right now, as far as I can tell…). Basically, any nice-ish shirt goes fine with a skirt, as long as you more or less match how fancy the skirt is with how fancy the shirt is. There’s also often a pretty big range of how dressy any given skirt can be, which is one of the things I love about them. πŸ˜€

      • My big issue is what to pair with the dressy ones (basically all my twirly skirts right now are pretty dressy, although I’d love some more casual ones.). I do fitted t-shirts (mostly black or white) with the casual ones, but how do you pair something a little fancier, say with a silk tier skirt? Or other full, fancier skirts?
        Other than t-shirts, I have the hardest time finding/figuring out nice shirts. I basically have nice t-shirts and tunic shirts (obviously not the best with a twirly skirt, but I like them with jeans and a belt). What else goes though?
        Thank you, I think a belt would look awesome with a shirt and a twirly skirt and I hadn’t thought to pair that way.

        • I know what you mean about the fancy skirts! I have had success with tops that are essentially t-shirts but have more “blouse-y” details, like lace or some structural element, or are made of a material other than cotton, that makes them feel more fancy. I also feel like sleeveless tops tend to look good with fancy skirts for some reason. If I’m still stuck, I look at catalogs to see what they pair with that type of skirt, and look for something similar in my price range.

    • Hi, my name is Hintzy, and I have an addiction to twirly skirts…

      I keep an eye out for skirts at places that are not malls… the farmers market near me has a few stands run by middle eastern and indian families – they carry some awesome skirts and are pretty reasonable for the price (like under $20 is my usual rule of thumb). That might not work for people who don’t live in the coastal metropolis suburbs, but if you do – look there. Also, it might be easier than you think to make a paneled A line skirt if you have a sewing machine.

      As for what to do on top, I like to do a solid colored shirt that is fitted, like the $5 v necks at H&M, or a tank top and a cardigan (that’s not floaty) basically if the skirt is fitted you can be floaty on top, if the skirt is floaty then you probably want to be fitted on top. I wear my skirts year round with the addition of tights, fleece lined tights, and/or knee high socks in the winter. cut off sweat pants and knee high socks with boots under a long skirt is rediculously comfy in 20F weather… just sayin.

  20. Perfectly timed post! Over the last few months I have been taking note of my wardrobe and it doesn’t reflect how I see myself at all. Even being a former hairdresser I never ‘got’ fashion, it was always for other people. And raising my children full time doesn’t leave a lot of money for non essentials. However, I have found that just wearing slightly nicer shoes (as opposed to thongs/flip flops), adding a bit of lip gloss and some cheap statement jewelry has been a good start and already has given me a big self confidence boost.

  21. I found it really difficult identifying as “goth” during my university years then moving into a professional arena where this wasn’t “appropriate” anymore. I had to ditch my lip rings (I still miss them SO bad, but if I only put them in at the weekend it just makes them swell) and the leather trenchcoats and corsets and big boots. Sadface. I feel like I lost a massive part of my identity when I became a professional.

    Since then I’ve tried to incorporate little details whenever I can – skulls etc on jewellery or scarves, or crazy shoes (I picked up some purple and orange paisley ones in Paris and wear them ALL THE FREAKING TIME). But it’s still hard to just find excuses to dress up and feel like me again sometimes! (Especially since the FH only knew me in more recent times, so doesn’t really “get” the dressing up either)

    • I’m kind of in the same boat – EVERYTHING I wear in my free time (long story short, my style is typical of a blackmetaller: fitted band tees, skinnies, Docs, hoodie with band patches, lots of black, part of my hair is shaved) is not remotely compatible with a corporate environment.

      I see work as an opportunity to experiment with styles that might be too out-of-place for everyday as they’re fancier or more feminine. I still wear mostly black, but I wear a few color pieces on occasion so nobody can box me in as “gothic” and stick to classic, unoffensive cuts like blazers, dress pants, pencil skirts, and plain heels. The rule of using 1 statement item in a neutral outfit is useful and allows me to wear some OOT things to work without drawing too much attention. I can wear leopard print, huge art deco prints, damask, Barbie-pink pants, etc. without raising any eyebrows so long as I wear them one at a time in a purposeful way. Personally, I avoid: kinky boots, corsetry, tight-fitting outfits, showing shaved parts of my hairstyle, shoes I would wear to a club, collars, anything spiked. It sort of helps having an unpierced face, growing out my natural hair color, and preferring minimal/natural makeup; consider that if I had facial piercings, still had blue-black hair, and shave-and-draw brows, I could probably get away with less. Working in IT, as opposed to law, corp sales, or management is also a factor that gives me some leeway but we still have a business-casual dress code that leans more on the “business” side.

      There’s no need to sacrifice most of any free-time personal style if you need to wear professional clothing for work. Money may be an issue for maintaining two separate wardrobes of clothing, but I find it forces me to focus on buying only things I really like and will actually wear many times in both clothing realms. It may take some experimentation, though, to find a happy medium between being acceptable for work and feeling like yourself.

  22. This is very good advice. I struggle a lot finding my own ”personal” style while maintaining a professional/not-too-girly look at work, your tips are a reminder of what I need to do more!!

  23. Hmmmmm. I am also a t-shirt and jeans kind of woman, and work in a STEM field, albeit formally trained in the social sciences, and I love love love high fashion/couture (Alexander McQueen, oh my god, the recent collections Sarah Burton has been creating are just GENIUS). But I don’t like wearing skirts or dresses, it feels like the bad kind of drag despite the fact that I have no gender identity issues otherwise. And it is okay to be a jeans-and-t-shirt kind of woman!

    What I have done is invest in my jeans and t-shirts. Every single one of my jeans is tailored to my body (not as expensive as it sounds, I swear, especially if you live in your six pairs of jeans). My shirts are long-sleeved (preferably bell-sleeved, but do you know how hard that style is to find?) v-necks, which show off my collarbones and necklaces and keep me warm, and I only buy the ones that come in my favorite colors — crisp white and bright turquoise and deep emerald and sometimes they have embroidery on the cuffs. I have a few old band and activism t-shirts in the drawers for weekends, but I don’t really break them out much.

    There’s nothing wrong with a uniform that you’re comfortable in. Since I work in STEM, I can get away with jeans and long-sleeved tees at work; I have little to no thoughts on dressing in a corporate environment.

    All of my clothes make me happy. The colors, the fit, there is something in every piece of clothing I own that makes me smile. If there isn’t, I get rid of it.

    • Man, your sense of style sounds awesome. I try to work on a similar basis, with good jeans and shirts that flatter, but well, jeans and t-shirt environments beget more jeans and t-shirts, and I keep finding myself backsliding in the morning to whatever is comfy. That, and my favourite shirts are almost all a deep grey or black, which starts to feel repetitive.

      • I feel you on the grey and black + jeans = too much monochrome. Necklaces and scarves are your friend there, I think, as well as colorful cardigans or sweaters if you live somewhere that layering is a possibility. I mean, a black shirt is a GREAT canvas for a sparkly necklace!

        Flattering + comfortable is the best possible combination, I think — once I put my clothes on in the morning, I don’t want to think about them for the rest of the day. One of my friends likes fussing with her clothes, making sure the skirt hangs right, that her necklace isn’t twisted, etc., etc. Which would drive me crazy.

    • Awesome! Sounds like you’ve found something that is definitely you, AND it’s a sweet grown-up version of the old formula.

      Just to clarify, there is absolutely nothing wrong with being a jeans-and-t-shirt kind of woman! But when for me that means defaulting to unflattering college t-shirts with ripped jeans, just because I don’t know anything better to do and it isn’t making me happy, it’s time to change it.

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