How To Wear Menswear (Without Actually Looking Like A Man)

Getting the so-hot-right-now menswear trend right without literally looking like a cross-dresser can be hard. Too often we try to master slouchy and just end up baggy, (a la Katie Holmes bf jeans misfire). Here’s how to rock it and still look like a chick. A really hot chick.
Tailored Shorts
Not to be confused with your standard tailored shorts, menswear-inspired ones will generally be made out of the sort of fabric you could picture making up a men’s suit without too much difficulty. They’re a good way to switch up your work wardrobe and a bit more forgiving than your standard shorts. That said, if you’re one of those girls who’s always complaining about her knees or thighs, these shorts are not for you. [$49, Banana Republic]

  • First let’s talk about the fit. See how the ones pictured are fitted through the waist but don’t cling to the thighs? That’s ideal. Rarely do you see men sausage casing their legs into pants, if you’re going for the menswear feel, you shouldn’t either.
  • We’re lovers of ladies’ ties and bow ties and pairing either one of those with a standard, fitted white blouse will leave you looking full on adorable. A black mary jane heel will do wonders for this look, too. [$47, Karen Walker, Revolve]
  • If the sexy school boy approach is too literal for you, just go for plain old sexy with a detailed blouse like this one. The nipping in at the waist is important: You don’t want anything that’s baggyall over or you’ll end up looking like a sloppy girl/guy with his/her shirt untucked. [$58, Victoria’s Secret]

Slouchy Khakis
Here we have the perfect example of a masculine pair of pants that manage to be both slouchy and sexy. This, ladies, is what we call the ideal situation. Once again, notice the close fit through the waist followed by a looseness through the hips, still an essential part of getting menswear right. [$115, Vince,]

  • You truly cannot go wrong pairing pants like these with a black, loose tee that does a bit of clinging and flashes a little bit of cleavage. In order to end up with a top that clings in the right spots, light, floaty cotton is essential. [$78, T by Alexander Wang, OAK]
  • For something a tad dressier and more figure-forgiving, the cream peasant-ish blouse is a good bet. It’ll still hint at your shape without looking like a standard tee. Plus, the gathered bottom allows you to mess it about, maybe pulling on side slightly above your hip and the other a little lower and then acting like it happened on its own cause you’re sexy without even trying. [$68, T Luxury, Antropologie]

High Waisted, Wide Leg Pants
We. Love. These. Not only do they give you a little thigh camouflage and make your waist look tiny, they also hide cankles and somehow manage immense hotness even with the max coverage. [$207, Organic,]

  • You will be the coolest person in the room in a cropped, ’80s inspired top like this one with your high waisted pants. Really. As long as you don’t have any exposed belly button showing, a huge chest and under boob fat that’ll roll in a way you wouldn’t like, it’s not trashy. Not one bit. [$38, Silence & Noise, Urban Outfitters]
  • A casual corset like this one (tucked in, of course), will take you in a sexier, night out direction. Throw on some chunky silver bangles and you’re good to go. [$40, Topshop]
  • Note: If your pants get any longer than the ones pictured, you need to take a trip to the tailor. Good news is that these are straight legged so any alteration should be cheap, fast and easy. Ideally, they should hover about an inch above the ground, safe from street grime.

The Boyfriend Blazer
First off, do not take its title to heart and literally shop your boyfriend’s closet. Unless you’re a lady footballer and he’s a willowy little thing, that blazer will not fit. Conveniently (if confusingly), there are “boyfriend blazers” for women. Like this one. It should fit through the shoulders and be a tad long–hitting in the top 1/3 of your butt region–but slim. [$108, Aqua, Bloomingdales]

  • Wear it with a floral dress. Sounds counterintuitive but looks quite cool. The dress should be fitted at least in the top portion and then the skirt can be a bit more flowy if you like. Because of the length of the blazer though, shy away from really puffy skirts. And if you’ve got the bod and confidence for it, a super tight number will be damn hot. [$58, Kimchi Blue, Urban Outfitters]
  • A tee or tank with a tight, biker chic mini skirt. Must we say more? [$94, Mmmunt, Pixie Market]