Girl Meets Boy

Menswear collage 2

There’s nothing new about women in menswear. Coco Chanel, Katharine Hepburn, Marlene Dietrich, Diane Keaton all became icons of menswear-inspired style. Lately we’ve been awash in boyfriend jeans, boyfriend sweaters, boyfriend jackets, brogues, fedoras….  I certainly get the appeal. Menswear worn by women conveys a confident, insouciant attitude.

Karen pointed me to this October article in the Wall Street Journal about fashion insiders shopping in the men’s department for wardrobe basics. Nothing particularly new there either, but it’s interesting that the focus is on value as well as style. (If you can call $275 shirts a “value,” but the point still holds at lower prices.) I’ve been tempted to try menswear, especially after seeing how much better made men’s clothes seem to be.

“Men have a lower tolerance for high price tags and expect higher quality,” Mr. Grant explained. “They want to buy a sweater and have it last forever.”

But in the past when I’ve tried either men’s clothing or even some menswear-inspired styles for women, I’ve found that rather than looking insouciant and chic, the effect is well, a bit… butch. (Butch is a valid style choice, but it’s not what I’m aiming for.) Back in the 1980’s after reading a profile of Tina Chow where she mentioned that she loved wearing men’s white cotton undershirts, I dashed off to Thrifty Drug to grab a package of Hanes. The shirts were nice, a soft and heavy cotton, but looked awful on me. I gave them to a neighbor.

I’ve periodically tried on men’s jackets, but somehow the effect is always…

David Byrne big suit

The women who really can carry off menswear (at least the clothing) tend to be a bit more on the tall and/or willowy side.

At J.Crew, president and creative director Jenna Lyons said the men’s cashmere sweaters are a big hit with female customers, so she often requests them in brighter colors. Two years ago, Ms. Lyons introduced a women’s version of the company’s popular men’s Ludlow jacket. The blurred gender lines are a part of the brand’s DNA, Ms. Lyons explained, recalling that, when the company was run by Emily Woods (daughter of founder Arthur Cinader ) in the 1990s, it offered unisex sizing. “Emily did this because she liked to wear men’s clothing herself,” said Ms. Lyons. That’s also true of Ms. Lyons, a willowy 6-footer who has bought menswear all her life.

For those of us who are a bit curvier (or short, or both), it gets tricky. The line of most men’s clothing is basically designed to drape from the shoulders, and a bust gets in the way of that. “Slouchy” or oversized on a curvy body can easily read as “sloppy.” My short stature also complicates shopping in the men’s department, as few, if any, men’s clothes are designed for a 5’1″ frame. I’m willing to have alterations done on a superior piece, but a simple men’s shirt that fits my bust is too big in the shoulders, too long in the torso and arms, and huge through the waist. Sweaters hit me mid-thigh. Boys’ sizes are too narrow in the hips and bust.

Another thing I’ve noticed about women who successfully incorporate menswear into their wardrobe is that they often choose pieces and fabrics with a bit of movement, drape and fluidity. Look at the suit Katharine Hepburn is wearing in the top right picture in the collage at the top of the post. There’s nothing stiff or starchy about that fabric. Likewise with this picture below of Coco Chanel from the WSJ article, you get the sense of movement in those trousers even though they’re structured. (I’ll grant that probably neither of these were actually men’s clothing, but rather custom made based on men’s designs.)

Coco Chanel menswear

I love outfits that mix masculine and feminine elements, but find that in general it works best for me when the “masculine” bits are shoes and accessories. A bespoke suit is a nice idea, but has little place in my life.

Are there men’s items in your wardrobe? Do you have them altered? What do you look for when shopping for yourself in the men’s department?



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  1. No menswear items in my wardrobe. I agree that you need to be tall AND willowy to pull off a good look with menswear. I have the tall, but not the willowy.

  2. Same thing here…the shirts make me look quite round…not a good look. Have been experimenting with men’s ties, as a belt and fem scarves tied in traditional mens’ tie knots….not having much luck with that either. LIke the whole idea but doesn’t seem to work for me. Cathy W.

  3. I love the look of menswear but with my HH chest, its not a reality. I do wear neckties on occasion but with my women”s shirt and jacket. At this point, thats enough for me.

  4. As close as I get is stealing Le Duc’s cashmere mufflers. I am 5′ 10″ and average weight with long legs and I can’t wear men’s clothes- the shirt armholes are too big, among other fit differences. With so many menswear pieces cut for women, why bother? Also, what is cute on a 23 year old- men’s plaid flannel boxers and a rugby shirt- is not so appealing on me, 40 years older,

  5. Except for suits/jackets and “man-tailored” shirts, I just don’t think this is true anymore. It’s also the free tailoring/alterations that one gets as a matter of course in the men’s dept.

  6. I’ve never tried shopping in the men’s department. I love the look, but I think you are right……it’s for the tall and slender woman. I’m 5’5″ so I think I need fitted clothing. I did see a brocade tux that I tried on and it look great. I was in women’s sizing so it fit, maybe I will get it.

    blue hue wonderland

  7. I used to wear slouchy suits back in the 80’s and I really loved that style, my hair was shorter and so, much curlier and I liked the juxtaposition, I would really like to brogue up, I might try in spring/summer when I can go back to ankle length trousers.

  8. Absolutely agree. My approach is generally through fabric, so I might try to pick up a menswear vibe through grey flannel or tweed, as in a favourite box-pleat skirt or a pair of dark, fine wool, tailored pants. I like to wear brogues, occasionally, or military-style boots with a skirt or dress. But otherwise, at 5’3″ I can’t afford too much bulk or sloppy fit.

  9. “Menswear-Inspired” is the closest I get to actual menswear! I have the ‘man-ish’ Michael Kors watch and a pair of oxfords, but as much as I appreciate the slouchy appeal of boyfriend jeans, when trying on in a dressing room, I look like a tree stump standing in a very deep hole! I own a couple of boyfriend cardigans for very relaxed occasions, but always feel sloppy and somewhat unkempt. And LOVE the look of a crisp white shirt worn alone, but have never pulled that off to my satisfaction, either. Always wear mine under sweaters or cardies. So no, I don’t do menswear !

  10. I have a couple of men’s cashmere sweaters I picked up at Goodwill and a wonderful men’s scarf. I rarely shop men’s departments in regular retail…but when I thrift…I always stop at men’s! I often will find sweaters which are high quality and fit really well…and I am curvy!

    1. Idem. I’m absolutely the wrong build for menswear – short, plump, busty and hippy (and was busty and hippy even when very young and slender) but I do look at pullovers. I have a very, very warm merino one on right now, on an utterly frigid evening. I paid $2 for it at a charity shop, and it seemed brand new.

  11. I am 5’1″ with an ample bosom so men’s wear is totally off my radar.
    When I paint in acrylics I wear a men’s shirt as a smock with the sleeves rolled up,
    and I wear a man’s ESQ watch but that is about it for me.

  12. Love love this post, but mostly just love this blog. I stumbled upon it, directed by Pinterest, and have spent hours scrolling the pages. I’m 28 years old and find endless outfit inspiration for myself as well as for my mom, who has hit a real fashion roadblock at the age of 62. I so appreciate this blog as a space to direct her to when she needs reassurance that stylish options do abound for women who are past the days of low rider jeans and cheap Forever 21 tops. Endless thanks!

  13. Nobody likes a tailored look more than I do, but I sure as heck look for it in the women’s section of the store. We are sorta kinda built the same more or less. 🙂

  14. I wish more designers would offer us the same quality as men . British designer Margaret Howell pays the same attention to detail in her women’s range as her men’s . Jacket sleeves & trouser waistbands etc are just as immaculately finished . I still choose carefully though . At my age , in a man’s cut of overcoat I can look like an old bag lady .

  15. Sometimes my boyish figure comes in handy. I’ve embraced the boyfriend jean fad (scored two fine pairs for less than $4 each via Goodwill) and one of the half dozen basics I bought before my shopping sabbatical goes into effect is a man’s dress shirt, thrifted for $6, and inspired by Patti at Not Dead Yet Style’s fabulous incorporation of menswear shirts into her wardrobe.

    P.S. Fixed the Bloglovin issue!

    1. I didn’t realize I was in the minority. I’ve been purchasing my cotton shirts from the men’s department for decades. It started when my Father died and I was given all his beautiful cufflinks. The only way to consistently find French cuffs were in a good men’s shirt. I’m not tall at 5’5″ but I am on the slim side. I do like that word willowy but it somehow doesn’t apply. A small men’s will fit a woman nicely and with the length it also works well with leggings. I’ve worn a mans watch long before it came in vogue and the only thing I took from my ex were all his lovely silk pocket squares!

  16. I tried my future hubby clothes often but does not work for me either most of the time
    I like how Patti’s of Not dead yet style does the man’s style, wearing a masculine shirt with a girly skirt – that is pretty on her – I wonder how it would look on me?

  17. I love the look but can’t wear it. 5’4″ with an hourglass figure. I do have 3 men’s watches and wear them all the time. One is my husband’s; he no longer wears watches, uses his cell. But I think of them as statement jewelry.

  18. I have the lack of curves required, but am too short for menswear to fit me and/or look any good. My teenage daughter buys shorts and t-shirts in the boys’ dept because she doesn’t like ‘girly’ colours and designs and doesn’t want to wear shorts that are small enough to be underwear. And the clothes she buys there are cheaper!

  19. I have to admit my wardrobe is absolutely exclusively menswear – I thinks its pretty dull, but thats life. I’m stuck with it – the downer of it all is that it doesn’t even look good on me haha

    I think David Byrnes big suit is just stunning !!

  20. I agree with Tiffany’s daughter, and buy my shorts from the boy’s department or the men’s if the waist is small enough. I wear men’s shirts on weekends, and men’s small sweaters during the week (and my dad’s from college/Air Force days, 60-plus years later, on Fridays and weekends). I hate suits and so don’t bother with men’s, women’s, or boys jackets. Men’s watches, cuff links, and menswear inspird trousers, loafers, smoking slippers? I love them. I usually wear either a fitted top, loose bottom or the inverse, and think men’s clothing is less ridiculously colored than women’s.

  21. When my father died, a sister-in-law sent me a men’s zip-neck cotton/cashmere sweater from Brooks Brothers. I’m 5’4″, 120 lb, mid-size bust. That sweater is just about the most comfortable clothing item I own that is wearable outside the house. I don’t know why it seems so comfortable, but it is. I also have one of my father’s old sweaters that is also fabulous. So maybe for me, actual menswear is limited to comfy, loose sweaters, and for other clothing items, as others have said, I stick to “menswear-inspired” clothing.

  22. I like the look of men’s clothes tailored for women, especially if they’re sort of glam, like the photos you used. I have a couple of men’s shirts, but I do try to avoid looking too butch. With my short hair, small bust, and thick waist I could easily look too manish!

  23. I have a couple of thrift shop sweaters and the brogues, but that’s about it. When I was in my early 20s & 20 lbs thinner, I wore my boyfriend’s clothes all the time. Those days are long gone.

  24. First – thank you for your wonderful blog (long time lurker, first time commenter). You inspire me to ‘step it up a notch’. I am in the Navy so most of my life is ‘menswear inspired’, but in my private life, I rock it exactly as you suggest – shoes, scarves, watches. That way they don’t interfere with my not so mannish body. As a 38 year old woman, my best menswear outfit this year was a slim cut gray tee with a bit of drape, slim cut black cigarette pants (both women’s department), no socks, my patent brogues (Navy, we have the best shoes!), a large man’s watch and a draped cream scarf (men’s department). Classic, understated, on trend.

  25. I realize that even MEN look bad in menswear if they are non-standard shapes- for example, if they have big round butts or thick thighs. Most mens’ clothing is cut for slim-hipped men with average to narrow thighs. I know a number of men who have to resort to bespoke tailoring to get pants or shirts that really fit. But, unlike women, that option is there for them.

  26. There are men’s shirts in my wardrobe and I often pinch Mr TNMA’s things (scarves/jumpers) but these days I tend to stick to women’s styles that look mannish. I’ve always been a bit of a tomboy so I live in jeans/brogues/Chelsea boots/jackets.

  27. I have always worn a “mens-wear” type of look, but never bought in the mens’s department. I like “men’s” fabrics, a blazer in a herringbone, brogues or loafers, man tailored shirts, but in a silkier fabric, etc. At a time in my life when I went to a lot of black tie events, I got a black tux pants suit and wore than often, sort of my signature look as I couldn’t afford many different gowns, and I liked the look on me. And I’ve worn a man’s watch since I was in my teens. You have some nice choices up there!

  28. I stole my brothers’ oxford shirts when I was a teen – and flat-chested! I spent most of my 20s and much of my 30s in Levi 501s. Love the look, but I can’t seem to pull off the baggy pleated mens slacks in my 50s.