Dress Like a Man, Think Like a Girl

Girl, not to be confused with lady because there is a vast difference.


During a requisite conversation with a close male friend some three months ago, he divulged what seemed like the opinion that wouldn’t end about the way in which he would dress had he been born a woman. I didn’t ask for the assessment but that didn’t matter. Before this particular conversation, he had been eager to let me know that if he were me, he’d have worn pumps in place of cape shoes virtually every time I brought my Alexander Wang pals out for a spin. When I’d wear unusual silhouettes in even more unusual fabrics, like a chartreuse sack shaped something, his response to the wears would never fall along the line of “that’s what you’re wearing?” but would instead reflect his inner fashion female. “If it were me,” he’d say, “I’d have opted for a classic pair of denim shorts with a cool airy blouse.” He finished this sentiment with, “it’s so easy for you girls.”

I looked at him in bewilderment. On the one hand, how much longer would he continue to pretend that he didn’t drink skim cappuccinos, wear leopard lining on his insides, if you know what I’m saying. And on the other hand, Easy? In a market so over-saturated, one oozing with talented designers, some so fixated on creating the next “it” trend, we the consumer, often get caught up in their game of rise to the top and subsequently turn out falling, how could he possibly dub the fashion conquests of our day to day, “easy.” I put myself in his shoes, hoping I might understand what he was getting at a bit more clearly but ultimately realized while standing in his three year old Adidas sneakers that this wasn’t about me. This was about him and his fervor to step outside his square-ass box. See, here’s the problem with finding yourself stuck in a box in this day and age though: we live in a world where there ultimately is no more box. We can’t “think outside the box” anymore because that shit doesn’t exist. How then, can you possibly find yourself still living in one? I gave him a small dose of his own unfortunate medicine and concluded that if I were a man, not he were a woman, I’d be running wild circles around him. With ease.

Denim blouses paired with straight leg denim jeans, nice burgundy belts, loafers–no socks. Colored pants, white pants, boxy blazers. Interesting shades, dyed hair. Murses! A certain Emily Weiss uses the most majestic Coach men’s dob-kit as a handbag every so often.

I got to thinking about it more internally. It dawned on me that in the last couple of months, while I hadn’t shopped very often, the only times I had purchased anything were of the male variety. This particular friend and I found ourselves at the new A.P.C boutique in the west village a few Sundays ago and I indulged my upper body in two blouses. One plain white–it could put Lands End to shame, but I’d never turn my back on that discovery–and one pajama striped. Blue and white with brown buttons–it was the exact color contrast I’d been looking for in all my women’s shirts. At Uniqlo shortly thereafter, I was looking for the proper proportionate loose fit white jeans. The female versions all rendered too tight so I looked toward the mens apparel where I found, not only a perfect cotton twill trench coat, but a very small pair of white jeans that would thereby be dubbed my Asian-brother-jeans. I ripped them at the knees and at last: Current/Elliott brilliance.

Forward by Elyse Walker is notorious for hosting some of the most provocative offerings high fashion has to offer. Charlotte Olympia, Givenchy, Jil Sander, it doesn’t matter. The mens sweaters are wear my heart is. Note: Uniqlo’s cashmere crew necks are everything and not in the fashion girl sense of that word. Just kidding, that’s precisely the sense I’m depicting. On a similar site, Mr. Porter reminds me on an almost daily basis how regretful I am to have been plagued with a foot so small I can’t even so much as ponder the notion of purchasing mens shoes. Unless that is, I look to the little boys department which is theoretically not a bad idea–thanks for helping me through that, guys.

But what does it all mean? Has womenswear taken a turn for the uninteresting? Likely not. Have I? Maybe. But I think this might be deeper than that. It may in fact tie back to a control tale as old as the 19th amendment. Is this a game of role playing? Am I using menswear as a vehicle to quantify an absolute sense of equality? I was always told, “dress like a lady, think like a man,” but maybe that ism isn’t the most successful way to conquer what needs conquering. Maybe we need to scrap the “lady” all together. Dress like men and think like girls. Girls are genuine, awesome, playful and often get yeast infections for staying in their wet bathing suits too long, ergo ideal Man Repeller.

Recently, I have found that my male friend hasn’t had much to say about my wears. I’d imagine because they are precisely what he’d like to be wearing. Nevertheless, I’ll further explore this hypothesis and report back. In the meantime, what say you?

All photos shot by Tommy Ton.

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  • Elise and Margot

    So cool! Love it ūüôā

    x For Happy Days

  • Shanice Khoo


  • Shanice Khoo

    I think women’s fashion has been too widespread. It is hard to find a blog with invigorating mens fashion. And men probably care less, which makes it even more intriguing! I love mens fashion, to me, it’s harder to put together a palpable outfit for them than it is for us. Oh well.



  • generally, ALL i am interested in is the male, y chromosome variety. boys have all the fun!

  • Dudette

    I work in retail. Dressing men in 1000x more natural to me. I wanna drag women back to the men’s shop and say OK NOW…thats where the magic happens.
    i think womens clothes ARE boring, in a predictable-styling sense. oversized shapes and different prints/color combos made specifically for men are lacking in girls clothes. i dont want florals. i want fun ass stripes, pinstrips, gingham.. 

    • Maureen

      ¬†Funny, I have been saying men’s clothes are so boring.¬† Minimal color options (blue, black, brown and grey), cotton, denim, wool jackets & suits, low quarter shoes.¬† Men invented high boots – but we can’t wear them now.¬† And how many boots look masculine!¬† Maybe if clothes were just put out as clothes – and wear what you like.¬† Get rid of gender specific styles – just clothes.¬† The Romans conquered all of Europe in tunics – ie sundresses!¬† N one laughed a them!

  • Sam

    You are the coolest of the cool. 

  • Jasmine // WebHauteJas

    i have most def worn the above outfit {white/black striped tee, red pants} …thats a” go-to” for me!!

  • Leigh Ann Fisher

    I am so over florals and the mom of three girls. What they put on shocks me sometimes. It’s as if they rolled out of bed, slapped on the tackiest shit they could find and call it fashion. Guys on the hand have been playing with the same colors and prints for years. I think it’s easier for them than us. We are overloaded in what is fashionable when we should just listen to ourselves and figure it out own our own. On that note, I’m in yet another strapless dress and I love it.¬†

  • funny you are finding those basic gems in men’s because I have to look to women’s for bold print and color ūüėČ

  • ClosetCravings

    Sometimes I think we over-analyze fashion. Fashion is meant to be fun and playful. One should simply wear what they feel good in. =)
    Satisfy Your Cravings For Celebrity Style and All Things Stylish and Sweet

  • Emilie

    Yes! I very much agree with you.. My favorite piece in my wardrobe is a mens grey cashmere sweater.. That i paid a dollar for. I just feel sexy in it! And comfy, and actually very feminin. Nothings like a mans crisp white shirt.. That is something you reminded me of!

  • I do this all the time. Take inspiration for men’s fashion, there’s a real freedom that comes with it.


  • Chelsie M

    Amazing article as usual!



  • Alexandra

    I LOVE this essay!! ¬†It’s thoughtful and funny and an overall joy to read. ¬†I like that it’s slightly less sarcastic than usual. ¬†I love my sarcasm, but it’s nice to hear a slightly different tone. ¬†Book material? ¬†

  • As a menswear blogger I can’t help but find myself both sporadically jealous of and inspired by the women I read about, i.e. you. It seems that not only are the options larger for women but just so much more easily accessible. Living in downtown Toronto, seemingly everywhere I turn there’s a new womenswear boutique popping up out of the already peplum-saturated street. What does that mean? I dunno. It just seems that no matter the sex or height of the heel, the grass is always greener.¬†

  • KZ

    i spent the last six or so years going on first dates in filmy white tees and skinny jeans with boring-ass ballet flats and inconspicuous accessories. i cannot thank you enough for pointing out (what should be) the obvious. i am proud of my love of art, my various advanced degrees in art history and consequently my love of fashion and various degrees of man-repelling bib necklaces, high waisted pants, and loafers of the penny variety. and since fully embracing your way of life (ie: just be yourself and wear whatever the hell it is that makes you happy), I too have found myself with the perfect manfriend. he may or may not wear a canadian tuxedo to our wedding. with bowtie. obviously. 

    lobeee your blog. keep doing what you’re doing. and you’re a knockout. andddd that’s all folks.¬†

  • Well, at least, we’re lucky to live in London, or Paris. They do care about clothes. In Russia, they just don’t. ¬†And, yes, my man’s jumper is the best jumper in the world.

  • Me Gusta o No Me Gusta

    Mens are wearing girls shoes everywhere, so we do the same and its perfectly acceptable. 
    Great post!


  • Angels of the Night

    Women still have something to prove and until the job is done, i will try whatever!  LOL

  • Mariposa

    Great outfits!
    k√ľssien from germany

  • marinacasapu

    In Europe men are more stylish than here! But unfortunately america (the majority of americans) )sees and portrays their style as gay…


  • Becckitt

    I agree–women’s fashion has become a bit boring. I think it’s partly due to trends filtering down much more quickly (or maybe I’m just noticing it more) from the runway to fast fashion chains. It also seems that we’ve ushered in the era of Pinterest style–the cute, uber-girly clothing styles that girls repin the shit out of (see: anything floral, braided, pastel, or long, flowy and chiffon). I’m guilty of it as well, but I’ve definitely seen a lot more girls recently wearing things that are very similar to the pins that do well on Pinterest.¬† Just a theory, but I do think Pinterest has changed the way we dress.


  • Sketch42

    Ha! I just today wrote on my blog about how I was in topshop yesterday and the only things I wanted to buy were from Topman. Also, I was wearing Boy. by Band of Outsiders, and also I think I was born the wrong gender. 

  • Calla Nassif

    I have massive feet (size 10) on a good day. I have often pondered buying men’s shoes but have stopped myself short – hoping to not make my look…. well, mannish. You’ve given this once forgotten desire new legs. Off to the men’s shoe rack i go!!

  • nataluya85

    i do this daily!!! dress like a boy, think like a really immature feminist teenager!


  • MIukoridi

    Dress like men has never been so cool and comportable, I always try to pair oversize mens shirts with skinnies or parka with a short silk dress & booties. Mens fashion works for me, especially considering that I have no hips… I think if you have a boyish figure, mens items look even bettr on!

  • Oppositelipstick
  • Madisson

    We were actually discussing this the other day at work. I think men’s fashion has been getting attention lately largely because of the oversaturation you mentioned that’s plaguing the women’s department. Menswear tends to have a certain easiness and nonchalance that we always strive for, making it very alluring. There are far too many designers doing womenswear that are hyper focused on coming up with something new and different, rather than just perfecting and slightly twisting established basics- which is what menswear often does so well!

  • So true!






  • Lisa Daniels

    magic magic! 



  • Love this post. Menswear has always been popular in women’s wear and it’s only become more popular with the vast variety in prints, cuts, and general overall comfort. Bravo on a topic well addressed.¬†

  • Isabel Y Chen

    Small feet? Try children’s size 2, a women’s 4 in heels. For whatever reason, size 4 flats are still too big. Sad times.

    I think men’s clothes are boring, but in a classic way. Their styles don’t change too much, as far as I can tell. The lapels on their coats get a new slit here or there, or get wider or narrower, but it’s always essentially the same: shirt, jacket, tie, pants, and shoes. In that sense, I think shopping for menswear is a bit of a relief from the hectic and turbulent tides of women’s fashion.

    • Arxsyn

      I think men’s fashions have to be more clean in line and yes, while the template is the same, the devil’s in the details. The excruciating minutiae in male suiting alone is mind boggling yet fascinating to me. Not all men are chained to pants. Some are enlightened to wear kilts too!

      I have tiny feet like you. They’re a half size smaller than yours though and infinitely harder to dress. There’s no physical retail store that carries my size. But thanks to the miracle if the Internet and a vintage store I’ve acquired a number of high heels. Ok, 10.



  • Serdane-elie

    OH yes ! It’s so funny because I do the same about the difference between my male nature and my female way of life and conception of fashion.


  • Mady

    this is fun! cool outfits…



  • Guest


  • I believe women have the world on their feet when it comes to fashion. I have written, a while ago, about the immense advantages we have in the toilet rooms due to the fact that we can wear skirts — envy the penis no more. We can wear skirts, ladies. And dresses. We only need shoes and a single piece of clothing to be fully dressed (ok, it would be recommendable for most of us to wear some kind of support for the twins, too). And we have the entire masculine wardrobe at our disposal. A man in a dress looks rather bizarre — did anyone enjoy seing Marc Jacobs in black lace and white undies? A woman… we can do it all and look really good.

    So I don¬īt think we should dress like men and think like girls. We should dress like women, and think like women too, because that means having every possibility.


  • Men typically dress for themselves.¬† We girls have a tendency to dress for everyone else…ergo – harder.¬† Maybe once we start dressing how WE want to dress and not worrying about what the guy across the street reading the newspaper, texting, drinking coffee and biting his nails thinks….it will get easier.¬† One can dream.

  • the coattail effect

    I think men’s style isn’t as versatile as women, but that being said, they also can’t be called out for dressing skanky


  • When I last lived in Japan a few years ago I found myself gravitating towards the men’s fashion. ¬†Partly because men’s clothes in Asia are cut for slim builds so it’s easy to wear them as a girl. ¬†But also because I felt like the women’s fashion was either boring and professional or ultra-slutty and fetishy without a lot in between. ¬†These days I am coveting some of the men’s outfits I see in Korean dramas.

    I just found this blog today and I’m loving it! ¬†Gotta read some archives now.

  • jlondon218

    saturated market… you’re right on with that. dress like a man , think like a girl… i like that concept. it couldn’t have been seen any better.¬†

  • Pull it together!

    Argh! Nothing pulls on my heart strings like a well-dressed fella! Thanks for sharing. 

  • I love men that dress good. Ones that have blue hair are cool too.


  • Myblissisthisway

    very interesting post, love the pictures that you provided too!  its hard to find a well dressed AND fashionable men!


  • Leslie


  • One of the best things about being a girl is that we can wear and combine both men’s and women’s clothes, and pull it off with sass! That, and the fact that we’re able to think outside of that non-existant box in ways that men still have some catching up to do.
    Really loved this post… One of your most insightful and thought-provoking ones yet!¬†

    ardena rose

  • Seekingstyleblog

    Haha this is an interesting post!

    xo Jennifer


  • totally agree with you! ¬†there have been some great leaps made in menswear. ¬†as a dude who loves your blog i feel that it is a great time to be a guy in fashion. ¬†we are finally starting to get some attention and better options.

  • JM

    Leandra, posts like this are what give your blog meat – they underscore the brilliance of your blog’s philosophy. And so, as a reader, I am incredibly happy to see this post. And as a male reader, I could not agree more. However, what happens when the equation is reversed? You may have an easy time finding great finds for yourself in the men’s department, but what about men finding great finds in the women’s department. Women’s sweaters and shirts are often too small for the average male body; pants too shirt; and skirts too tight. Men don’t have the same accessibility that seems to make it easier for you and other women to shop in the men’s department. Furthermore, the last few seasons have been saturated with “menswear” looks in womenswear, thus creating clothes that looks like men’s but fits like women’s. When was the last time men found “womenswear” inspired collections? Your friend may not be living in a box – he may just have harder access to the creativity and brilliance of womenswear.

  • guest

    This is the most thoughtful, intelligent post you’ve written! So smart. I like that you’ve kept true to the Man Repeller tone, but are introducing more thoughtful content that goes beyond ridiculous outfits. Hope to read more like this!

  • Claire R-M

    always the best reads!!! 


  • Whaaa? Men have half the silhouettes women have and one tenth the prints! I think it is laughable to say that women are cornered in the world of fashion and that they have to turn to menswear. I suppose attaining a certain oversized fit is another thing. But finding a particular fabric or color… puh-lease.
    Not to mention shoes, bags, make-up, etc.
    No I’m not a cross-dresser nor do I have any motivation to dress like a woman but it is surprising to hear an article from this perspective and hearing women reaching into a man’s closet so exhaustedly. I ENVY the selection that women have.
    So go out and enjoy your VAST assortment.

  • I have discovered the wonders of menswear since I moved in with my boyfriend. We’re about the same size so I can wear his awesome shirts, jackets, hoodies, t-shirts… I don’t even care if it made my personal style boring or whatever, it made it really easy and simple and that’s what I’m all about. That, unicorns and the universe.


  • Sabina

    I definitely can’t argue about there being no more “outside the box.” Of course it’s all been done. Still that’s doesn’t mean it’s necessarily easy for anyone to find their style. Or that it can’t be interesting when someone revives a look from 15 years ago, or sticks with the classics as long as the outfit has some sort of edge or rocks a pair of cape shoes. It’s not about shock value, but, as this blog has so often pointed out, dressing in a way that impresses YOU.

    And I’d love to see your take on menswear trends.


  • Alice

    I think shopping at mens sectioms is very clean amd straight forward. You have your oversized blouses (ca-ching!), your jeans-that-we-girls-can-turn-into-denim-shorts (ca-ching!) and dont get met started at bowties… Conclusion: no confusion

  • vira

    love the rhetoric ”
    ¬†Am I using menswear as a vehicle to quantify an absolute sense of equality?” its a feeling a lot of us are left wondering about without being able to phrase it exactly like that.¬†

  • The notion of shopping for men’s apparel is¬†soo much more exciting than womens. It never follows the conventional shapes of a womanly body,¬†so we are able to tweak everything to suit our style. MENS APPAREL 4 LYF!¬† P.S. men do have it easy in a way¬†as they have fabulous¬†women like you to give them style advice.

  • Zoe Arevalo King

    Love it! So tell me….Bondage collars, man repelling or man appealing?

  • All I can say is, I feel bad for men. They can’t wear dresses and skirts like women can. In a cool non-repelling way, of course.

  • abigail lind

    as someone who frequently steals clothes from boyfriend/brothers/dad/hobos, i feel you boo.  big time.  thinking like a man child!


  • Bel√©n cavas

    I love navy with red trousers and the last one picture i like the mix colors in that tshirt.




    First dude can get with us ANY time. 


  • Lotus Blossom Design

     Haaa loved reading this.  Rock that menswear!

  • Fkh

    Love it.. I’ve been noticing this as well.. I was shopping with my brother and couldn’t help but want half the things for myself.


  • Blaastyle

    It’s an amazing article you’ve written. I guess it makes me want to think about it too… I always take pleasure in reading your blog because you’re writing skills are really good and your pictures are always fun. Your blog makes me smile.¬†x Romi

  • christa

    Aside from the cool outfits that you put together, your writing voice is very intriguing and I never get bored reading your posts! Love it.

  • Sarah Wasser

    Perhaps my favorite post of all time. Get em girl! 

  • I don’t usually click on individual posts because I’m lazy and the internet ups my laziness by a lot but because I recognized the man in the first picture, the picture that can be seen from the MR home page, from my current favorite series on YouTube (Model Files), I clicked. And I’m glad that I did. Lately, I’ve gotten very tired of what we as women are being told to wear and especially because I’m on a babysitter’s budget (I’m 17), I don’t get to indulge myself in the spectacular treasures that are featured on blogs like these. Also, I like the idea of shrinking the gap between the clothing expectations of the genders. It’s always puzzled me that regardless of the season, men will wear long pants, socks, a¬†long-sleeved¬†shirt, and a jacket at a formal event while women are expected to wear a dress that is short and usually tight. That standard doesn’t make any sense and I think that it’s about time the fashion community and the rest of the world creates more equality of dress.¬†

  • This blog is so fabulous I cannot believe I haven’t stumbled upon it before!! So hilarious!! We <3 your blog! Check us out and find some fun, fabulous & unbeatable fashion ūüėČ you won't be disappointed! xx,¬†The Golden Girls

  • liuccia

    agree.. recently my fav blogs are blowing up with interesting mens fashion and women’s is just a bore.. unisex clothing line where are you??

  • Ekah

    this is a great post. like really, really great.  

  • italianchick

    In this new and ever-changing generation, we have gotten to the point where men and women can (in most ways) be coinciderd the same, therefore we have been given the liberty to express our selfs with a vast variety of things among them: mens clothes.
    Where years ago we had different faschion statements for men and women. Men pants and ties, women long skirts. And as well as specific gender roles. With time we have been able to brak trought hose bariers and free our selfs and fashion sense.
    So we can almost be coinciderd ribellious of gender roles but as well as fashion.

  • Tania_here

    Before reading this, i was telling a friend of mine, that if i¬īd be ¬†a man, my outfits would be certainly more √ędgy¬® (if you may). Told her i would probably have millions of sneakers and all types of ties in my closet.¬†
    Men’s clothes ¬†for me, allow you to have far more less ordinary ensambles….

  • veyron_cat

    Very good article. Congratulations! Personally, I think that women that can pull off men clothing are just… well, awesome really ūüôā
    Hope that you¬īre having a great day.


  • women are the new men. ¬†

  • Chelsea Tubbs

    I’m so impressed by your work, it always gets me thinking a bit deeper than your average ‘fashion blog’. Please continue providing us with something a tad more thought provoking., love it!


  • TheGreenHedgie

    I have an unhealthy obsession with menswear. I went into all the high end boutiques and haberdasheries in Dublin just to see if there was a size 3 men’s loafer available anywhere, I finally found a pair of fabulous black and white oxfords, I wear them practically every day. I actually find womenswear to be more boring than menswear because I find that many girls and women these days dress like clones with their sundresses in bright florals, toms, skinny pants, and god awful tylersesque tshirts (do they have tylers in states other than texas?). Where menswear done right is full of clean lines, sexy shoes and even sexier suits. They can still wear bright colored pants but, instead of paired with a flowery top, thin belt, and gladiators; it is paired with a crisp button down, cufflinks or a straw fedora, and oxfords. Men may not have the most options but in my opinion they have the better ones.

  • There was a period back there a bit when I felt like I REALLY had to hunt to find anything particularly out of the box for women. I love lots of colour, prints and interesting shapes, and the runways felt sadly devoid of any of this kind of action – with a few notable exceptions. I did find plenty of treasures in the local designer sphere here in Australia though. I kind of feel like fashion for the fellas is still a little sensitive to having pushed things too far in the 80s and is venturing tentatively out of the box. The gals love it, but it remains to see whether the lads will embrace it…

  • Jackie May

    Men’s fashion really agrees with me. I have a rather curvacious figure and sometimes I don’t want to show it off. Therefore my go to is a baggy t shirt and jeans. My uniform is porbably 15% men’s clothes. And I’m proud of it. What I’m trying to get at is what you say has value and I appreciate you’re opinion. Especially the bit about thinking like a lady.

  • H&M Men’s section is my Mecca for tops and sweaters and hats. Really the only girl stuff I wear is probably my jeans but that was not always so. I believe dressing like a lady means more then wearing a dress and pearls. I believe it means to cover it up and carry ones self in a strong yet modest way. I don’t believe I need to think like a man per se to be successful for they do always say behind every powerful man is a woman. I believe that some men feel stagnant in their fashion due to lack of real options while we have so many. I do not feel that having so many options is a bad thing it just means a bit more self discovery is needed to find ones real style and to figure out how to best showcase that style.


  • Esme McGlasson

    Rei Kawakubo said it best…

  • Justin Gaberial

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