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 would like to share my own experience to maybe help those on a budget and struggle with weight variances.

    Growing up I had three different influences that helped me figure out my “style”I have now. My mother, who was a beautiful ,albeit irresponsible, fashion figure in my life bought and “borrowed” (IE PERMANENTLY “borrowed” ) her wardrobe items. She helped me dig through clothes left in boxes of evicted tenants in local apartments. She helped me figure out that thrift stores in “rich” neighborhoods had the better stuff. (Things like brand new clothes with price tags on them and more variety. ) She also introduced me to the world of pure underground shopping which was just a mix of yard sales, asking friends and friends of friends for old clothing, and goodwill and salvation armies were our “mall”. Shopping with her brought my creativity and imagination. If you like the thrill of the hunt, and clothes with a good price tag, this is the way to go. The only issue I’ve found is finding varying sizes. When I was younger this worked well with my body and build, but as I got older and curvaciously freaking awesome, it became bothersome to see a load of stuff to only be able to fit in just a few things. That being anything above the 2X sizes.

    Second influence is my grandmother on my father’s side. Budget aside, this woman would get me my school clothes from dress barn at full price. Granted, I had some great pieces that lasted me for years…(of course before my mom “borrowed” those as well). I will say this, I was thrifty somehow in my genes from the beginning so I learned that yes even Old Navy, Charlotte Russe, Vanity fair, Target, and yes…even Eddie Bauer has clearance items..like plus size jeans for ten bucks. =) Through careful research of sales, I’ve been able to catch a LOT of name-brand clothing for my budget formula easily through patience and compromise. So though my grandmother did NOT help with the budgeting part of this, I did notice and learn that even those scary expensive-looking stores can carry items a LOT cheaper than you think. Even asking discounts on damaged items helps too (as long as it doesn’t say as-is, otherwise its not a flea market and they will look at you with deep-seeded anger if you try and negotiate.) Oh and after working at a mall, for those REAL green lovers out there- retail clothing stores DO throw away certain clothing they deem unsaleable. As long as you aren’t committing crimes, dumpster diving for this stuff can truly be worth your time, as I know some people have made local ebay businesses out of doing this.

    Last but not least is my frugal grandmother who had no sense of style, but her budgeting mantras have helped me all through my life. Everything from “If its not on the way, I’m not wasting the gas to get there.”, to ” If you’re old enough to receive allowance, then you should be able to reasonably buy some of the things you need AND the things you want. Budget badly, and you’ll just have to do without!” (This was applied for school supplies..YES! I DID buy my own with allowance and coupons at the age of 8 and WAS NOT SCARRED FOR LIFE!! She built up rewards systems so the less money I asked for other than my allowance, chores and grades worked on a commission system that worked for us. She was a VERY OCD organized lady. I’m not kidding, she would cry if it was raining and she had planned to do something outside. Still love her to death though. Her simple cut-and-drive budgeting advice made a lot of sense and still makes sense to me now.

    Personally my budget goes as follows,
    $5.00-$10.00 for blouses and shirts.
    Up to $15.00-$20.00 for dress pants,up to $15.00 on jeans.
    up to $30.00 on dresses. Depending heavily on the quality and occasion.
    Accessories need to stay under $10.00
    and Shoes I splurge up to only 50.00$ depending on the quality and use for. sandals must stay underneath $10.00. Flip flops should stay underneath $2.00. Boots can go up to $100.00 heavily depending on quality and use.

    I have varied from size 14-22 and this formula has worked for me for over a decade in four different states. I have had to walk away from some AWESOME and BEAUTIFUL items. But I always remember that clothing is just a thing and that just because its pretty does not mean i should put a ton of money towards it. Clothing is a reusable source that is always in a cycle. Styles will come back and I may have another chance to wear them. but who knows? My sense of style may change, I may change, but I know I won’t something simple as clothing rule over my personality, my money, or my confidence. I “make” as in I MAKE my clothes look good on me. Changing your sense of style will mean nothing if you don’t have the confidence to overcome insecurities and move forward with what you truly want. I wish anyone who read this article does realize this and will pull that confidence from within themselves. Good luck!

  2. The people who look best style-wise, are generally people who don’t really care what people think of what they wear. I believe everyone has their own sense of style, it’s just not always what we are taught is ‘fashionable’ or ‘feminine’. Personally, I live in skinny jeans, leggings, ankle boots and oversized jumpers. Until recently, I was called ‘a hobo’. Now suddenly I’m ‘following the trends’. Just wear what YOU feel comfortable in. Being comfortable = confident = enviable. To me anyways 🙂

  3. Here is my biggest thing and I can totally relate on the tech school thing, I am not finished yet and I am in my 30s but I always retreat to nerdy character tees, or a cute pin up look one day and a fun sort of boho style the next I can never find anything specifically me, and the Goth me from my teens and 20s is still following me as well when my mother buys me skull tanks and sweaters that are super goth, I love them everything about those years of style in my life I do still gravitate towards but who am I as a “grown up” mother of two adopted children and one bio? and most recently due to some family drama I have put on a lot of weight and I keep thinking I want to figure out who grown up me is, but is she this size will she stay this size will she decide to have another child someday what is it that this woman is going to do because it would be my luck that i do this I break it all down and “find myself” and then boom I get some bug that makes me lose 40lbs or, I get motivated and actually lose it some other way and then I have wasted all that time and energy figuring out who I am and then have to do it all over again for my new body, This is not the qualm of just whats my personal style, its who am I and that is where my struggle is internally, I love EVERYTHING about this article but it makes me really look at myself like DUDE crap or get off the pot already!

  4. This is really helpful! I also wore a lot of jeans and t-shirts in high school . I did pick a few things up working at Salvation Army, but when I went to college, it was back to basics! This helps me get back into the swing of things!

  5. I don’t have confidences in wearing dress or even not so girly clothes.. I do like romper.. But I just dare not wear them. All I have is shorts and tee shirts in my woredrobe.. I do see clothes that I like but I dare not even go near them.. Maybe I’m just scare of being judge by others.. There’s one point of time I just wear plain tee shirts until recently I started wearing tee shirts that have prints on it.. Got a few dress but didn’t wear it once.. Some advise pls! Most of my clothes are dark colors.. And I only have black shorts.

Read more comments

Comments are closed.