Style 911: How Do I Make “Menswear” Feminine And Sexy?

“I keep wanting to try the menswear-inspired trend, but every time I try things on I feel like a manly cater-waiter. I really need help rocking that look in a sexier, more feminine way. Thanks!”– Laura

It’s pretty easy to cross the line from menswear-inspired to just plain dressing in drag, and once you cross said line, you quickly go from sexy to dowdy and just a tad confused-looking. But we’ve been hugely in love with menswear-inspired womenswear for a while now, so get ready for a whole lot of tricks and ideas.
If you’re just starting out, try a wool short instead of full-on wide-leg pants. Make sure they’re not too short– slouchy and at least mid-thigh is a good rule of thumb– or you’ll just look slutty. [$23, Forever 21]

Pair your shorts with a tailored blouse. Rebecca & Drew make awesome blouses that are sized by height, body type and cup size for those of you have have a hard time with blouses. If you do something simple like the black Rebecca & Drew shirt above, roll up the sleeves a couple times and add a girl tie and maybe a chunky cuff bracelet to make it a bit more playful. You can also pick a somewhat sweet blouse (right) that has built-in detailing. The bow at the neck is adorable and would look great with a brooch stuck through the center. Bonus points if the brooch is vintage (try eBay for that). [black shirt: $195, Rebecca & Drew; white shirt: $49, Armani Exchange; tie: $45, Zazzle; brooch: $20, eBay]

Ditch the flats for killer heels with a manly twist. And, of course, you’ll need some opaque tights to keep from looking like a moron wearing tights in the winter. [pumps: $875, Christian Louboutin, Saks Fifth Avenue; tights: $20, Topshop]

As with the rest of the outfit, you’ll want your bag to skew towards the masculine side of feminine. Something fairly solid with heavier details (as opposed to ruffles, for example) works best. [$160, Topshop]