Reader Request: Menswear Looks for Curvy Women

How to create menswear influenced looks for curvy women

Reader Eliza had this request:

I’d love to see something about wearing menswear inspired outfits when you have a curvier shape. I’ve seen so many cool photos and have many classmates who shop for little boy’s blazers, wear suspenders or flat caps, chop their hair short, etc. Somehow these things never seem to work for me. Real menswear doesn’t fit and adds twenty pounds, clothing that was actually designed for women loses the masculine edge, and it all looks sloppy or dated on me, rather than nonchalant and cool. Right now, the only way I can get a hint of this look in my closet is through tweedy fabrics and my beloved wristwatch (which is still a bit feminine, though it belonged to my great grandfather). Any styling advice you could give would be great!

I am still experimenting with and exploring menswear and androgynous looks myself, so this request falls a bit outside my comfort zone. But I’ll give it a whirl, then turn the question over to you knowledgeable folks!

Balance fitted and loose

This is good advice all around, of course: Loose with loose will simply swamp most figures, while loose with fitted allows some curves and proportions to shine through. Since relatively few menswear looks utilize dresses and since you’re likely to be working with separates, just pick one fitted item and one loose one. If you’re doing wide leg trousers, pair them with a fitted shirt or sweater. If you’re doing skinny jeans, a looser top can work. Careful, though, my curvy friend. If you’ve got a larger bust and hips you may want to temper a loose top with a belt, vest, or blazer.

Seek slim shirts

As Eliza pointed out, shirts designed with male-shaped humans in mind don’t look quite right on women with pronounced breasts and hips. That swamping effect, yet again. But there are contoured, fitted shirts available in this wonderful day and age, and many of them work for curves. I my own curves are in the butt/hip area and I’ve worn Banana Republic‘s fitted button-fronts. However, if you’ve got the dual curve combo of bust and hips, try Pepperberry instead.

Quest for a vest

In my opinion, a menswear-reminiscent vest is the ultimate tool for crafting fun androgynous looks. However, vests and curves sometimes fight and vests that work for curvy shapes can be hard to track down. So don’t add this to your shopping list and expect to find it the minute you saunter into a nearby mall. It may take a while. Even multiple seasons. But keep your eyes peeled for a vest that will cinch your waist yet sit above your hips, and also accommodate your bust line. I seldom use Kim K. as an example of stellar style, but this vest fits her quite well. Note that nice, low v-neckline. My guess is that her vest has a good percentage of spandex, or might even be a knit instead of a woven. (And, of course, it was quite possibly tailored …)

Embrace masculine accessories

Again, Eliza is already on the right track, here. Oversized watches, oxfords, ties, boots, plain-buckle belts, and fedoras are all far easier to fit to a curvy form than clothing. If you’re struggling to find menswear clothing that works, create a neutral-to-androgynous base with items like white tees, jeans, crew neck sweaters, or khakis and load on the accessories.

Image courtesy Amazon

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Originally posted 2011-10-04 06:02:26.

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43 Responses to “Reader Request: Menswear Looks for Curvy Women”

  1. Erin

    Shout out for Jones New York fitted buttondowns. I’ve got broad shoulders and a big rack, and they’re the only ones that fit me properly. Also bonus, they are made in plus sizes!

  2. Cynthia

    For someone who wants the look of a “menswear” shirt without compromising curviness, I found the PERFECT shirt. This one. Newly available in a bunch more colors. It looks crisp because the front, back and collar are woven, but it has side panels of knit material. My friend and I tried them on when we accidentally wandered into a Lucy store in San Francisco, and we both bought one. She has the typical “apple” figure where I’m more straight and they looked great on both of us. I’m wearing mine here. I’ve since acquired a white one and might go for the new dark red, too. I’ll wear an outfit with the white one today and post it.

      • Anne

        I bought two tops like this at Nordstrom. Virtually the same, but a believe they were a bit less expensive.

      • Bekka

        For cheaper options, you may also still be able to find this one at your local Target, which I like as well because it’s all cotton. I’ve also just seen them at the Evil Empire (otherwise known as Walmart). As soon as someone comes up with a formal version, I’ll be set for life!

        • E

          I bought two of those shirts from Target a couple years ago and I absolutely love them, since they are the first button-down shirts I’ve ever found that buttoned all the way down. One of them gapes a tiny bit in the bust area, but it’s nothing a well-placed piece of garment tape can’t handle. For whatever it’s worth, the medium fits my 34D chest and 28″ waist with enough room to layer over a camisole or tank top.

  3. coffeeaddict

    Menswear has always been one of those style options I’ve always wanted to try myself but due to my body shape all experiments ended horrifically.
    I would suggest to Eliza to try the following combination: feminine wardrobe with some cool male accessories. Something that has traditionally been the sole domain of men: cuff links, pocket watches and ties for example. This is where it can get very creative like scouting out vintage watches and cuff links and turning them into statement pieces.

    • Jen

      I know I’ve seen some pocket watch necklaces on Etsy which would kind of combine the masculine and feminine, I think. I like the look of ties on women–especially if it’s in a pretty pattern or color. I think thin ties can look better on curvy women because it falls better between the girls. Also I’ve seen a belt made from two coordinating ties sewn together–can’t remember where I saw it or I’d post the tut. Maybe check out places that have jewelry for men. That can give a masculine or rocker edge to an otherwise female outfit and might actually fit better if you’re curvier/heavier. Solid metal pieces, leather bracelets, or chunky rings are a neat look for women.

  4. Gwen

    While I usually try to downplay my long torso, it actually works well for pulling off menswear looks. I seek out tall sizes when shopping for button down tops–even though I’m kissing the underside of 5’5″. Aside from everything fitting in the right places (who knew?!), the added length has the side effect of de-emphasizing my curves.

  5. Maria

    How I, the definitely-an-hourglass-who’s-1.60-cm-tall-and-on-the-edge-of-plus-size-girl, do it:

    – pick colours that are traditionally used in menswear, such as black, grey, white and navy, with a touch of red or brown.
    – high-waisted, wide pants are a godsend. I found my favourite pair in a thrift store, and saw lots of similar versions there. The good thing about those “old” ones are that they’re usually rather fitted in the waist, but still wide enough for my hips and thighs. I pair them with simple, stretchy cotton button-ups with 3/4 sleeves.
    – old leather messenger bags are an instant masculine touch, whereas a very soft, girly bag does the opposite.
    – SHOES. Flats, of course, and particularly anything resembling brouges or military boots. I sometimes tuck those high-waisted pants into almost-military boots, and it looks great.
    – Accessories in general: anything oversize is good. Silver usually looks more masculine than gold. Structured is better than soft and floppy. Keep it simple and functional.

    Still, I always add something super-feminine as well, because it is the CONTRAST between masculine and feminine I like, and it definitely works well with curves. 40s hair, red lipstick or diamond earrings does the trick for me (though rarely all at once, of course).

      • sarah

        I am a novice at the menswear look but must agree with two points:

        1. Old Navy sells some great fitted button downs
        2. Adding one striking feminine touch seals the deal. I am not curvy by any stretch, definitely bean poll-ish, and I risk looking tooo boyish with the menswear trend. I curl my hair and wear pearl earrings and viola… outfit comes together.

  6. meg

    Two good tips for menswear-y dressing: boy blazers and any old dry cleaner/tailor. Boy blazers are great because they fit in the shoulder rather than being giant and man sized but they’re still boxier than a traditional women’s blazer. Get thee to the thrift store – another benefit of thrifting boy blazers is that they’re usually barely worn (likely having been bought for one wedding/funeral/christening before being stored in a back closet).

    A tailor also helps because you can buy big tweedy menswear pants and get them taken in to your own proportions. Or get subtle darts put in really crisp menswear button ups so they flatter rather than just hang like a costume.

    Oh, and depending on the circumstance/your comfort level, tweed shorts over thick tights is a great look for fall winter that suggests boyishness while being kind of sexy and feminine at the same time.

  7. Alice

    Thanks so much for this! I had kind of accepted that as a curvy woman I wasn’t really going to be able to do the whole menswear look this season but these are some fantastic ways of incorporating it into my wardrobe. Wonderful post Sally xo

  8. Elizabeth Ann

    I recommend my go-to menswear inspired formula: any top + any dark colored pants (preferably dark wash jeans) + blazer in a neutral color + menswear inspired shoes. Optional scarf for colder days. The shoes shouldn’t be too hard to find. The look has become so popular that there are a wide range of options for every budget and shoe size. The blazer may sound tricky, but it’s really not. If you are wearing the look for a casual occasion you don’t necessarily need the blazer to be a perfect fit. If it fits elsewhere but won’t button across your chest just leave it open all day. Long and loose is also acceptable as long as the rest of your outfit fits proportionately (Sal, I thought your tips were spot on here). One budget option would be to purchase a man’s blazer at your local thrift store. Look for something that fits well (but not perfect) in the shoulders and ignore the rest of the fit for now. You may be able to find one that gives you the look you want right off the rack, but if not the key element to consider altering is the sleeves. Altering sleeves is going to be cheaper than major reconstruction to the jacket, and if the sleeves fit well the too long or open and baggy look of the rest of the blazer will seem intentional. Katie Holmes and Victoria Beckham aren’t my usual style icons but they’ve both rocked open blazers in a variety of shapes and fits.

  9. Courtney L.

    I second the comment on tailoring. I don’t generally do heavy menswear-inspired looks because it feels like going back to the oversized 80s styles that I wore when I was 14. However, as I read you suggestions about where to find things that will fit a curvier shape, “Men’s suits are tailored” kept popping into my head. If I were to branch into menswear-inspired styles, I would start with a quality, thrifted blazer and/or vest in a neutral fabric that fit me in the bust and get it tailored to fit. I would also consider having button-down shirts tailored if I couldn’t find any that fit close enough that the vest would make up the difference without looking sloppy.

  10. Courtney L.

    My comment above was not meant to bash anyone doing an 80s-inspired look. I just personally can’t bring myself to wear things I wore as a tween or young teen as it comes around again. Well, OK. I could wear the silver mary janes again, but that’s about it.

  11. Katharine

    I’m curvy, and I actually very often look better in men’s pants that hang off my hips than I do in allegedly “woman” shaped trou, which far too often gap or bag at the crotch. Of course, YMMV. (That fits in with the discussion of proportion yesterday, actually. If I find the right pair of loose-ish, flat-front men’s pants and wear them with a long close-fitting top, the combination surprisingly makes my stumpy, short-torsoed figure look much longer and leaner.)

    Anyhow. I didn’t come here to talk about my pants, but to recommend a site (for which a friend of mine writes articles). is directed primarily at genderqueer and “masculine-presenting people” but has great advice for anyone with a female figure who wants to stylishly wear men’s fashions.

    • Clarice

      Thank you for the recommendation. It’s a really interesting site and one I never would have stumbled across otherwise.

  12. Patti @ NotDeadYet Style

    I am not that curvy, but I avoid menswear because it overwhelms me – so these tips are good for me too. I like a fitted vest much better than a blazer, for example. And I love a man’s watch!

  13. Elizabeth

    I’m curvy and I love Brook Brothers’ non-iron shirts. I sometimes have to use a little fashion tape or wear a camisole to address some puckering around the bust line. I buy them when they go on sale. Or – let’s be honest here, my mother buys them for me. She found out about them because Oprah raved about them on one of her “favorite things” shows. My mom now gives them to me and my sister (and brother, and husband, and father) and declares each Christmas “I’m just like Oprah! I give away my favorite things!” She’s a very waspy white lady, but, yes, my Mom’s just like Oprah.

  14. Elizabeth

    Regarding men’s watches – anybody know of any men’s watches made in a smaller scale? My husband has thin wrists – thinner than mine and has avoided watches for a long time because he can’t find ones that fit. I finally bought him a square-faced Kenneth Cole one a few years back with a leather band that suits him. I’d like to get him one with a metal band, but every men’s watch I try with a metal band does not fit my wrist so I know it wouldn’t fit his.

    • Katharine

      Metal bands with links can be adjusted by a jeweller. I’ve had watches like that in the past, and links can be quite easily removed and the band reclosed at a smaller size.

    • Tara

      You can get links removed from metal watch bands at any jeweler or usually anywhere you buy the watch. My husband always has to have some removed too.

    • Sarah

      If you get one of the ones with the individual links, the store can take out any excess to make it fit. Hubby has had to do this with at least 2 of his…

      • Elizabeth

        Yeah – I’ve tried that, but, no joke, the actual face of the watch+side hinges is often too broad for his wrist before we even get to the taking out links part. Hmmm.

  15. Bubu

    I’m quite hourglassy AND have broad shoulders with a short neck to boot, so I tread very carefully on this trend. My faves so far: stacked or platform oxfords, both brown and black, with pants or leggings or tights, are a nice twist on menswear. Also, I picked up a v-neck sweater with argyle pattern down the front- I somehow think of that as a bit meanswearish, but the fitted shape, vertical pattern and vneck keep it from feeling too broad. I like it with jeans or skirt or slacks, quite versatile really.

  16. Autumn

    Ooh ooh! I met one of the women behind Campbell & Kate ( and their shirts are amazing. They’re geared toward busty women and their button-down shirts do a great job of giving a professional line without looking bulky or dowdy. I’m not particularly curvy (and don’t wear button-downs anyway) but I’ve seen these shirts on hourglass-shaped women and they look wonderful, and it’s high-quality fabric.

  17. Anne

    This is really not in my wheelhouse. I’m built more like Kate the Great herself: “Not many curves but the ones she has are choice.” I recommend the blog Tomboy Style. It has lots of great style icons for inspiration and plenty of diverse examples of modern, and dare I say, still feminine, Tomboys.

    Happy experimenting.

    • Clarice

      Another great recommendation, thank you! I have always felt inspired by women with strongly menswear inspired feminine looks but have never done much with that inspiration. This article and comment thread are filling me with motivation I didn’t know I needed.

  18. Kate

    I’m a size 20, and consider myself curvy, though I know that I carry most of my weight in my hips and butt (I’m a D cup, which I realize sounds to you skinny girls like I’d be busty, but proportionately, I’m really not). I’ve recently started experimenting with men’s wear. Here are some of my favorites. Sal, you really hit a lot of things on the nose! Oxfords. They’re super in, super cute, and obvi, men’s wear inspired. Trousers. Jeans, and cords both look great, and for my big hips, I find they balance me out. With a tucked in button down, it can look feminine and masculine at the same time. Love it. My vest. I used to work at Old Navy, and about a year ago, we got a vest that was uncharacteristic for ON, a cord vest that came in chocolate and olive. I knew it wouldn’t be a big seller, because typical ON shoppers don’t go for things like that, so I waited until it went on clearance, and with my employee discount, snagged it for $7. It is seriously one of my favorite things to wear. It makes me feel classy, and it makes my waist feel defined, and I just LOVE it. So, hang in there, and keep looking. It’s possible to be a men’s wear chic bigger babe.

  19. Vildy

    I’m not liking the Kim K vest for this look because it seems like the reader is looking for a certain nonchalance and it’s anything but nonchalant.

  20. lisa

    My body shape has changed in the past year: I’m a 34C in the bust now and my waist is still quite small. So hard to find a fitted button-down that fits my torso without gaping open at the chest! I packed up most of my button-downs for donation and these days am now opting for silk button-down blouses and tunics. They’re not as constricting as fitted cotton button-downs but still channel a bit of masculinity into one’s look.

  21. Laurel

    Sweater vests are another great option for curvy women who want a menswear inspired look. One of my favorite winter outfits is a charcoal gray sweater vest, dark colored top and brown corduroys.

    • Jen

      That reminds me, if you’re at all crafty, it’s rather easy to buy a fitted sweater at Goodwill, unhem the sleeves, and hem them back to make a custom sweater vest. I’ve done this with jackets and blazers as well to make vests–harder to find vests in plus sizes I’ve found.

  22. Aziraphale

    LOVING the comments here. So many good suggestions. The menswear/androgynous look is one of my favourites, and I’ve been focusing on it lately because I’m boyishly shaped anyway, so why fight it? For me the bigger issue is that I’m very petite, so often menswear-inspired clothing totally swamps me. (Any suggestions would be welcome!). But I think I’ve got the button-down-shirt-with-skinny-jeans look down right, and as several people have suggested, having menswear-inspired shoes helps complete the look.

    One thing that has not been suggested, but that works for me, is a menswear HAT. I recently bought a — trilby? fedora? not sure what it’s called, but it’s black felt with a narrow brim that goes all the way around and tips down in the front. It’s cute as all get out when worn with the right skirt. I think it works because of the contrast between masculine and feminine elements in the outfit. I don’t like it as much worn with an already masculine outfit.

    Sal (or anyone), speaking of waistcoats (vests), I have been on the lookout for one for at least a year, with no success. Do you have any suggestions where I can look?

    • Katharine

      H&M has a whole selection of vests right now (at least, my local one does). Many black ones, and some greys and pinstripes too. They don’t fit me, because nothing “fitted” at H&M ever fits me, but they might you.

      My best luck finding vests has been in thrift stores. They keep coming in and going out of fashion, so there’s almost always a few decent specimens at my local thrifts (buried though they are among hideous boxy 90s teacher styles with appliqued cats on them).

      • Aziraphale

        Thank you, Katharine! I’ll stop by H&M with my fingers crossed.

  23. Tabithia

    The best vest I ever had was from Lane Bryant. I was lucky enough to find it for $6 at a thrift store. It was a halter style but it was grey with a very small plaid/checkered? pattern on it with a tiny bit of purple so it worked well with a fedora, button up and wide legged pants.

  24. Sonja

    I love the menswear look so much, but it usually doesn’t flatter my face, which is already a bit masculine, so there are some things that I’m avoiding. But I love my oxford shoes, and in winter I wear a brown tweed newsboy cap for a hat. I love it and it looks really good with my facial features.