Style
Where the runway meets the street

I’m just going to come right out and say it: men shouldn’t wear shorts. Their legs are hairy, gross and some have even been decorated with shitty tattoos. There isn’t a man on the planet that looks better in shorts than pants. In a perfect world, we would all live in climates that allowed men to comfortably wear pants year-round.

But the world is far from perfect, and on a blistering summer day (in New York City especially), it’s simply unfair to expect my fashionable male friends to suffer through existence in jeans or trousers while I feel the breeze in a pair of microscopic hotpants. So while pants are always a better look than shorts, if you absolutely must liberate those fuzzy man gams, I’m here to help you do so in the least offensive manner possible.

When it comes to dudes in shorts, the most important factor is length. Of all the unpleasant areas of a man’s leg, the thigh is by far the most unpleasant. So while some of our European readers (and even some of you over at the Highsnobiety Berlin HQ) may find this stance to be controversial, short shorts are a hard NO – I don’t care if they’re Kappa x Gosha. No one ever watched Wet Hot American Summer and thought, “Boy, those guys look cool. I’d like to look like those guys.” Shorts should never cut more than an inch (maybe two) above the knee. I cannot stress this enough.

While jean shorts are a popular option, they’re trickier to pull off than men seem to think. Too tight and you’ll look like the sort of Williamsburg hipster bro you’d find chugging craft brewskis in McCarren Park. Too baggy and you’ll look fit for the parking lot outside a suburban mall. The sweet spot (slim, yet effortlessly relaxed) is elusive and, for many, nonexistent. The truth is it takes a certain amount of God-given lankiness to look cool in jean shorts. If you’re rocking a bubble butt or some thunder thighs, this is not your summer look.

If you feel as though you may be the (very) rare fellow who can pull this thing off, remember the cardinal rule of length (which is perhaps even more important when it comes to denim), avoid cut-offs (a rolled hem works) and destroyed denim (lest you look like you shop at Hollister). In fact, Levi’s are probably your best bet.

The good news is that the most acceptable shorts option for men is also the most comfortable. The athleisure short has long been a staple for street style icons, and the look has never been more on-trend. While a drapey, drop-crotch pair from Y-3 or Rick Owens (you know, the kind that are practically but not quite pants) was once the de facto look, a fashionable basketball short feels a little more current. They should be quite loose and either graze or fall just past the knee. The look here is baggy baggy baggy, so if it’s not too sweltering, up the ante with a hoodie or a bomber.

Pair with kicks that are more fashion than function (like some leather Common Projects sneakers or even Vans) to avoid looking like you’re coming from the gym. This no fuss pair by Fear of God is a prime example:

If you’re feeling a little bolder, opt for this killer pair by Gucci:

And if you’re trying to not break the bank, you can’t go wrong with this option by all in x Champion:

If you’ve got to look a little more put together (or if athleisure isn’t and never will be your thing) there’s always the work short. I happen to think a work short should fall just past the knee (any shorter looks plain dorky). If you’re a tuck in sort of guy, a loose tuck will work. Top with an unbuttoned short-sleeved shirt for extra swag and finish with sneakers or oxfords (you’ll notice I’ve never once suggested sandals – if there’s one thing I hate more than seeing a man’s legs, it’s seeing a man’s feet). We love this classic black Topman option:

If done correctly, pleats can add a certain something to a twill or canvas short, but once again, mind your length. Too short and you’ll look like a prepubescent schoolboy. And please, never a short suit (I will never forgive Pharrell for that). With pleats, a loose tuck definitely works.

Stay cool, dudes (but not too cool).

Here’s what women really think about guys wearing ripped jeans.

  • Photography: Eva Al Desnudo / Highsnobiety.com
What To Read Next