world of men's style / fashion / grooming

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When It’s Okay (and Not Okay) for Men to Wear Skirts

  • Jessica Rusinak

Ewan McGregor

In light of recent shorts-related controversy here at Kempt HQ, some of us have been pondering the great gender-based injustice of summertime wardrobe options. While a man risks ridicule (and even threats against job stability) if he chooses to wear shorts to the office, a woman is allowed—encouraged, perhaps—to wear a skirt. The more sartorially adventurous gentleman may begin to consider a similar alternative to shorts... but please, before you make any moves we’ll all regret, consider our advice.

Herewith, Kempt’s rules for when it’s okay (and not okay) for a man to wear a skirt...


Someone has asked you to be his best man. In Scotland. Consider skipping the rental and securing a bespoke number. Keep it classy. At least until the after-party. (And obviously, if you are Scottish, anything goes.)

You’re attending a Halloween party as one of those Spartacus dudes. Good lead-in for photo ops with any ladies in Game of Thrones garb. Just be sure your abs are still in beach-going form first, and watch where you’re swinging that sword.

You’re off to a metal festival. Pockets to hold your cash, flask, sunglasses, caught guitar picks—plus a refreshing breeze when the sun gets as brutal as the blast beats... Note: if you plan to crowd surf, be considerate of the crew and do wear something underneath.

Ensiferum at 70,000 Tons of Metal


It’s 102 degrees in the city and you’re headed to the office. And you don’t work for Marc Jacobs. (But even then...) The walk may seem less of a sweltering ordeal, but the risks here go far beyond those of mere shorts—sudden subway-grate gusts are no joke.

You’re going to Coachella/Pitchfork/Bonnaroo. Shorts will do you fine here. No need to chance a Tumblr scandal. (And leave the feather headdress at home.)

You are Kanye West. Sorry, Yeezus.