She. Him. 

Boys in Skirts, Girls in Button-downs... Cross-Gender Funtimes!

Full disclosure: I love a man in eyeliner. There’s something about a pretty-and-tough mix on any guy that I think most women find attractive: burly guys who don soft sweaters, leather-jacket-wearers with twinkly blue eyes, and the like. In reverse, few things have the sex appeal of a woman wearing a man’s shirt. Yet I feel like women are playful about gender and dressing — wearing ties, tuxedos, etc — and men seem hesitant to make the jump.

Granted, the metrosexual movement has done a lot to bring men out of the I-slept-in-this-shirt ‘90s phase, but I’d disagree with those who say they’re getting in touch with their feminine side with beauty products and skinny suits. Historically, men have been just as dapper (if not more so) than women — picture Louis XVI or the put-together gentlemen of 1870s New York. Granted, I think my first reaction to a man meeting me for brunch in a dress would be laughter, but any guy who’d play dress-up with you telegraphs confidence and a real comfort in his own skin. Then again, I also find a man in tights weirdly sexy (years in the theater, maybe), so I might not be the best judge. At any rate, for those willing to bust through some gender fashion barriers like Kool-Aid Man (“oh yeah!”), here are some to try.

Steal his T-shirts.
Ladies: Summer’s the perfect time for big, airy clothing. If you can’t afford Alexander Wang’s boyish shorts and faded jeans (Peep the drop-crotch! So spot-on!), a simple trip to the men’s section at Levi’s or your local Salvation Army will probably do the trick just as well. While you’re there, grab an oversize blazer and a big ol’ men’s watch. I’ve even seen gals styling men’s belts by cinching and tying them at the waist — it’s a great take on the knotted belts that were on the runways for fall.

Wear her jeans.
Gents: My family’s from cowboy country and nobody knows how jeans should fit quite like them: slim through the hips, tight on the thighs, with a straight leg. Now, for a lot of guys, women’s jeans just fit better — they’re slimmer and often have a hint of stretch. I also advocate women’s sunglasses for guys with narrower faces — those Ray-Bans are basically the same, just a better fit. I’ve also been seeing some great pink tones for summer (T-shirts, neon pink kicks and the like) and surprisingly delicate accessories (a slim, tight bangle or a slender chain) for men. I know skirts seem like a stretch, but consider a sarong at the beach. Trust me, they look cool.


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