Gender-bending fashion lines: How to look smashing in men’s clothing when you’re shaped like a woman

Guest post by SonyaG

This is not a post on gender-identification, and much less about sexual orientation. It is not a post on being trans or trying to pass. This a simple post on how to look good when gender-bending fashion from someone who has been doing it for years.

I generally rock a dapper look. Shirts, ties, vests you get the idea. Also, a word on my body type. I am tall and skinny with round hips and very little boobage. I would appreciate people with experience in cleavage to post their tricks, because I can’t speak from experience here.

Wear men’s shirts:

Like, literally, NOW. Men’s shirts are better constructed, better quality and there are so many more options than women’s shirts. And do you know what? Men’s shirts are loooong. They actually cover your butt and stay in your pants, unlike the annoying waist-baring cut of women’s shirts.

Try sizes and cuts to see what works. Men’s shirts kindly have all that info printed on the label! For me, that would be slim-fit. There are online shops that have gender-neutral shirts now, but I have not tried them yet. From what I gather, they are a huge help for people with boob fit issues?

Avoid excess flappy fabric that makes you look like a kid playing dress-up. There will be problem areas, for sure. Personally, I generally have too much loose fabric pooling at my lower back, where the shirt tucks into my pants. One way to minimize this is to wear either high or low waisted pants. Mid-waist seems to make it worse. Also, leave the bottom button(s) that are hidden in your pants undone. It creates a less snug fit around your hips, and you can tuck the shirt better. You can also just throw on a vest or sweater.

If you own a sewing machine, sew two darts up the back of the shirt. I promise, it’s easy. Pinch the fabric from high up, near mid-shoulder blade and create a crescent-shaped dart to where the shirt is in your pants. It’s just sewing two straight lines. You can do it, promise.

I have given up on sleeves. They are not worth altering. I just roll the cuffs. If you have a nice shirt with a cuff in a different color/pattern (cause guys shirts do that and it looks awesome!) there is a way to roll and not lose the effect. It’s called the gangster cuff, Google it.

Wearing a men’s shirt will not make you look like a man. Just like a better-dressed woman. Start with a plain white button-down. You can look absolutely femme if you pair it with a flirty skirt, leave a few buttons undone and add a necklace. And once you’ve tried it, you might get hooked. Just saying…

how to wear mens clothes when you are shaped like a woman


I love ties. They are the equivalent of statement necklaces. They add color, pattern and snazzy up an outfit. Go bold. I like to do the opposite of my shirt, pattern-wise. A patterned shirt with a solid tie or a crazy tie with a plain shirt. And I also leave my top-most shirt button undone for a more casual look. (Okay, it’s actually because I feel strangled all buttoned up.) Try a bow-tie too!


If you want to invest in proper tailoring for one item, choose a vest. A good quality vest in a classic pattern — like black or a subtle pin-stripe — that fits you well will become your most treasured possession. You can choose to have it tailored to mask or emphasize your feminine curves and waist. It will not only look amazing, but it will also help hide any fit issues with shirts.

Men’s accessories:

Try a hat. Or a men’s sleek belt. Or dapper-boy tooled leather shoes. Wear them with a skirt to better show them off.

Photo from Notorious-mag
Photo from Notorious-mag

Go all out dapper. Or not:

Sometimes, I purposely wear a push-up bra with my shirt and tie, just to muddle people. Not usually, but sometimes. Or pair a very feminine up-do with a strict business look. You can be as blatant as you like about gender-bending, or you can smile secretly at the feeling of subtly toying the line.

Tips on shopping:

It can be intimidating to shop in the men’s section. If you’re anxious, start online maybe. I say “maybe” because fit is hard to get right online even if you know your proper size.

Better to start in a big discount warehouse type place. You know, the one where there is no service if you need a different size and only one blasé attendant manning the cavernous changing rooms? My first time, I brought both men’s and woman’s wear to try. Even if I had no intention of trying on the dresses.

A word on dealing with judgey people:

Most people in my rural area, either assume it’s a fashion choice, or that I’m lesbian. I don’t much care what clients assume, and I am not about to embark on a rant on the difference between gender and orientation in the middle of the grocery store.

Just ease yourself into it until you are confident. The first time I wore a tie to work, after months of wearing men’s shirts and belts, I was pumped up. Bring on the comments, I was ready. There were hardly any. I think one older man said I “looked cute.”

The few degrading comments I’ve had can generally be dispatched with humor. “Is that a men’s tie?” Can easily be replied with “Well, it’s on a woman, so technically it’s a woman’s tie now.” Children can be brutal. I don’t hold it against them — I like to explain simply that I wear what I like and I like the color of this shirt and so can they if they want. If anyone persists in being a jerk, a firm “I like it,” and walking away, works well.

In conclusion, it’s just clothing

Wear what you like, what looks good on you. Don’t worry about a label, or which section it came from. You be unapologetically you.

Comments on Gender-bending fashion lines: How to look smashing in men’s clothing when you’re shaped like a woman

  1. I love this article. My daughter rocks a style she calls “gentleman girl”: boys shirts and blazers paired with leggings and tutus, comfy cargo pants paired with dainty blouses, and a mish-mash of accessories. I go all melty at the sight of a woman in a tailored suit, and personally prefer mens dress shirts over blouses as I can actually get them to button up over my boobs without leaving the button gap.

  2. Really, “when you’re shaped like a woman”? I love this fashion advice, but it seems exclusionary to imply that there’s a specific shape that makes someone a woman. How about: “How to wear men’s clothing when you’re a person with curves” or something along those lines? I’m thinking of all my trans sisters out there whose bodies may not fit your definition of womanly, but who are most certainly still women, and trans men who might have curves but are definitely NOT women.

    • You read my mind. I was interested in this article until the “shaped like a woman” part **Rolls eyes** What exactly is a woman shaped like? I’ve known many cis-women throughout my years and they were all shaped quite differently. The idea that women are shaped are certain way is quite frustrating.

    • With respect, I don’t think the title constitutes the author saying that all women are shaped the same. Or even what a woman is or might be.

      I read it as alerting me to the fact that this article is specifically about what it’s like to buy and wear clothes designed for the kind of body that society typically (and I am not saying correctly) designates as male if you do happen to have a body that society typically (again I am not saying correctly) designates female.

      Let me make it totally clear that I have a huge problem with society dividing bodies into two types and then designing and marketing clothes to only these two types, when all know that bodies and identities are infinitely more varied than that. We all know that prominent breasts and hips do not equal “woman” but society thinks they do and therefore clothes on offer to “men” do not accommodate humans with these features as well as those marketed towards “women”. This is simply a guide to how to navigate that if you are a human who is shaped like (what society calls) a woman.

      This article doesn’t cover the entire spectrum of body types and identities (which is an impossible task any way given that it is any individuals right to decide and create their own) and what it’s like to clothe them given the limited range of options based on the assumption that there are only two types of body. Given the article’s very specific title and the fact it’s clearly this person’s own experience, I think that’s ok. If the same article had a title claiming to be about trying to clothe all body types then that wouldn’t be ok with me because that’s not this article.

  3. This is a great start! I’m looking forward to comments from people with suggestions on how to wear men’s clothes when you have big (sexy) curves. This has what’s been keeping me away from buying/wearing men’s dress clothes so I’m ya’ll have some tips and tricks to share =)

    • Might I suggest just diving in and trying a few shirts next time you shop? Everyone’s body is different, and be prepared to try a few sizes, but I think you might be surprised.

    • I believe OP is referring to something like this:

      If you have a smaller waist / larger hips darts can be used to reign in some of that excess fabric around the midsection. Many women’s dress shirts have these already sewn into the shaping. The benefit of doing them yourself is you can customize how much darting you want (pinching in more or less fabric) based on how “fitted” you want the shirt to hang – or even leave them off all together. Start by experimenting pinching the shirt with clothespins.

      • Yes! This! I would post a photo but I have no clue how to go about posting a photo in a comment. A regular dart is usually more a triangle shape. I make the dart more shaped like a long slim half-circle moon so it tapers both at the top and bottom. This allows me to make the shirt fit straight up and down at the side.

        I agree that you can easily play with it to adjust to your body type. I use safety pins before I sew. My first times, I tended to start it too low. Up to at least mid-shoulder blade or more works for me.

        • And I’ll add that it is typically easiest for me to do darts if I can have someone else pull the fabric and help pin while I stand naturally. This way, there’s no awkward twisting for you and you can really see how the fabric will hang, hopefully giving you a more even dart.

  4. What about for petite women? I have a hard enough time finding pants and things in women’s sizes, and I just assume that any men’s pants that fit my waist and butt will be wayyyyyy too long…

    • The nice thing about most men’s pants is that they are sold by waist measurement AND inseam, though some combinations may be more difficult to find.

    • Personnally, I haven’t had much luck with men’s pants. I have too much hip and thigh compared to my waist and I get the dreaded baggy back-gap.

      However, this also happens to me with women’s pants.

      Oh well. You work with your body type!

    • I buy a fair bit of stuff from boys sections. Mostly I buy shirts, but if you’re very petite you might be able to find some boys pants that fit.

      • But please please, no boys ties! I had a well-meaning sister-in-law who gifted me with a ton of boys ties. They looked horrible. They were cheap and too short and several were clip-ons. *shudders* A proper tie looks posh, with rich colors and nice pattern and more importantly; it reaches your belt buckle. Otherwise you look like a clown. Skinny ties definitely work best for me!

    • We should switch. I love that some women elect to wear mens’ clothing, but due to my size (6’4″) I am often forced to wear mens’ clothing. Before the advent of internet shopping all my jeans and shoes and sweaters were designed for and sold as “mens” styles/sizes (and the pants still weren’t even long enough!).

      Maybe there can be a follow-up article– how to dress like a woman when you’re shaped/sized like a man!

      • Sounds like you need to start writing! I’m sure an article like yours would be a huge help to both tall girls and trans girls! However, since I am close to a foot less than you, I won’t be the one writing it! I am not a professional writer at all. I just felt I had something that could help others and that I wished I had read ten years ago. Go girl! Share your experience!

    • yes, you’d probably have to drastically take up the legs… so anything with a flare at the leg would be lost. But it works fine for chinos and skinny jeans, they can be taken up without looking odd. Its easy to take up pants, you can sew it by hand. And you can even just cut off jeans and let them fray.
      I am petite and so far I have figured out a few tweaks when wearing mens clothes. The darts in the back are a good help, having more boob in front they actually fit better and don’t gape like womens shirts. I also take in at the shoulder, as I have very narrow shoulders. I just love a lot of the patterns and fabrics in mens shirts too…. the colours suit me and of course, I never see mens clothes that can’t be machine washed and tumble dried. There is hand wash separately dry flat in the shade for mens clothes. I am so sick of my clothes falling apart. And… there is more cotton in mens clothes, I am not paying through the nose for polyester.
      The only thing I haven’t figured out is mens pants…. dress pants just have way to much fabric in the fly… I started wearing mens clothes slowly… it stated with borrowing my boyfriends jumper and finally actually being warm. So all my jumpers are from the mens. Then tee shirts and singlets. I have always worn mens socks as I used to steal my dads simple all black pairs. Now I am adding mens shirts to the mix.

    • Minimisers are great, I get very similar ones to the one you linked to from Marks and Spencer in the UK.

      Loads of support with those full cups and wide straps and the holding the boobs to you rather than pushing them away is more secure (and so less wobbly, like a sports bra but still with some shape). I tend to look like the prow of a ship in anything else and shirt closing becomes very problematic. An added bonus is that as they are unpadded and usually light on lace and trimmings etc they are comfy when its hot and sticky too.

  5. On dealing with judgy people: I’m inclined to agree with Eddie Izzard “They’re not women’s clothes. They’re my clothes. I buy them.” Clothing doesn’t really have a gender, wear what you want. People will get over or they won’t, and then you’ll know that about them and you’ll be happy either way.

    Busty ladies — fear not the men’s shirt! They are so much more comfortable and will not gap open! You can tuck them in and they will stay tucked in! It’s a miracle! You can buy really nice ones at the Goodwill and they will cost like $4. Unfortunately my waist to hip ratio is not compatible with men’s pants unless I alter them.

  6. I’m what I believe is “cello-shaped” as far as a body type (plus sized with a relatively small waist to boobs/hips). I’m tall so the idea of wearing men’s pants has always appealed to me, but unfortunately because of my waist/hip ratio the pants really don’t work. I haven’t tried the back darting on a mens shirt, but in general i find that shirts that are large enough to button over my bust are enormous in the waist. What I typically do with my husbands dress shirts is to tie them in the waist over top of a skirt or maxi dress. It’s nice way to diversify some of my outfits, stay warm, and avoid overuse of cardigans.

  7. Wow this is… my post. I’m a steampunk who discovered a STRONG love of gentlemen’s clothes. I grew up wearing my brothers hand me downs and was never particularly femme day-to-day (I do like dressing up but that just that dressing up). So discovering I could wear tailored gents style was so cool for me. (Esther Quek is a fashion idol JUST LOOK AT HER!)

    I found the best thing to do (with the D cup I have) was to find some well tailored ladies waistcoats (mine’s from pepper-berry) and combine them with shirts and braces positioned to the sides so they don’t get the awkward over boob effect. Braces are god’s gift, they hold your trousers up without constricting your waist!. The waistcoat covered any fabric gather.

    I get ton’s of compliments about my ‘style’ at work which makes me really happy. I also have my pride and joy a tailcoat I found in the back of a charity shop. I have no idea where it came from but now it works perfectly with my stripy trousers.

    • Well hello there, sister-in-gender-non-conforming fashion! 🙂 Nice to meet you! I am sure you look fabulous!
      And, uh, braces are suspenders, right?

      • Nice to meet you too.

        As for the braces… I… think so (British Lass here) not the ones that go in your mouth. The ones that clip to your trousers. Suspenders go on a garter belt over here 😉

  8. My first forays into combining clothes were with women’s tops and guys pants, normally cargos. I think it is cute, and then I have real-people pockets, instead of something that is lucky to fit a piece of lint. I’ve also done combinations of women’s dress bottoms and a top with a men’s vest.

    Mixing it up is the best! And guy clothes are just so much more well constructed and comfy!

    • “then I have real-people pockets, instead of something that is lucky to fit a piece of lint”

      One time I watched my boyfriend put his phone in his jeans pocket, and I did a double-take and it clicked in my mind: Wait, how DEEP is that pocket??? His phone was several inches below the opening. If my clothes even HAVE pockets, there’s no way they’re big enough to fit my phone all the way in. He amusedly rolls his eyes when I get on my pocket-equality soapbox. 🙂

      • I’ve been with my partner for nearly seven years, and it’s gotten to the point that now he gets on the pocket equality soapbox instead of letting me. 😀 Down with the pocket-archy!

  9. While I haven’t forayed into the land of some of the snazzier men’s fashions, I have discovered a love of wearing men’s jeans. Frankly I find jeans made for women to be too thin of a denim, poor construction, and often too fancy for me. The pants I’ve found in the men’s section are very durable, plus they have big pockets! Wearing a belt is a must though, because of course men’s jeans were not designed with women’s hips in mind.

  10. I’ve found some wonderful women who like men’s style clothing and can sew will also sell them! In australia I’m very fond of Charlie Boy Clothing. I have small boobs, so I can do mens shirts easily, but not mens pants, my waist and hips are not shaped for them. But now that I work out more, my thighs are too big for womens pants too! Annoying. So for now its all about leggings.
    I think if you look in some queer online forums for tailor recommendations, you could find a pro to help you alter any clothes, for any size boobs waist legs etc. Hopefully they exist all round the world! There are so many rad weddings with non traditional clothing choices these days, pro tailors have gotten on board. Or a sewing class- lots of sewing shops have short courses and I’ve found older ladies who have been altering their clothes since the 60s are often a bit alternative already!

  11. Men’s trousers and the gaping back thing:

    If you are having problems with men’s trousers being too large at the waist due to needing a size to accommodate hips and thighs, then one tip can be to get men’s skinny fit styles but in a larger size. This sounds mad but bear with me…..

    Most men’s jeans styles are generally straight legged (leg tubes same diameter all way along, no hip allowance) this is really clear in this image of a pair of jeans laid flat. These days even the straight legged type are also less roomy than they were even 10 years ago.,type%5BSTILLLIFE_FRONT%5D&hmver=3&call=url%5Bfile:/product/main%5D

    Women’s jeans (with the expectation of flares and bootcut) generally tend to have leg tubes that are be wider the hip and tapered at the ankle, even if you lay a pair of women’s straight leg jeans flat you will see this. So if you have hips and thighs that that are wider than your waist (and yay to that!) and you want that straight legged look (typically associated with men’s styles) then you will need extra hip and a little less at the ankle to some degree otherwise the extra hip width makes the lower leg part looks a like you are ready to hit a rave circa 1998 (although yay to that too!)

    Men’s fitted skinny styles have this wider at hip tapered at ankle shape, in the pic linked to below of a pair laid flat, you can see this, it’s subtle but it’s there:,type%5BSTILLLIFE_FRONT%5D&hmver=2&call=url%5Bfile:/product/main%5D

    If you get them in your exact size they will look like a fitted skinny jean (although not as much as women’s fitted skinny jeans) but if you get them larger, then that slightly narrower lower part of the leg will hang like a straight legged jean and the slightly wider top part will give a little extra accommodation for hips and thighs. The waist also tends to fit better with less gappage.

    My gorgeous sweetly butch wife who would not be caught dead in a skinny fit jean that looks like a skinny fit jean (but loves them on me) does this and it works like a dream, especially about the bunching at the back of the waist. It took a while to figure out just how much to size up (she goes up one waist size but it will vary for different bodies) but after the all the annoying and sometimes upsetting trying on, she now has a formula she can use to re-order online.

  12. This article is so inspiring! I love ladies who can rock a suit, but I always thought they managed it through…I don’t know. Some kind of witchcraft. Now I’m thinking about all the beautiful cufflinks I’ve passed up over the years. Le sigh.

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