Can You Do Shorts in the Office?

By John Ortved
Illustration by Tara Jacoby

I don’t make a habit of telling people what they should or shouldn’t wear.  It’s a losing proposition. At best, I come off as an effete know-it-all. At worst, a hater or a heckler. Style is personal. Be yourself. And all that.

On the other hand, when I’m asked, and even paid, to opine on style, well, that’s a whole other barrel of monkeys. Recently, my friend John asked if he (and by extension, you) could wear shorts to his office, and I have some thoughts. Many thoughts. So many that I thought I’d share them.

It’s less a matter of “if” than “how.”

Tailoring and propriety are like the CEO and COO of the same company. They’re in constant contact, and eat lunch together most days of the week. Their kids even go to the same school. The thing is, in most workplaces, you’re fine in shorts, as long as they’re properly tailored. You need to be able to move, and there should be no strangling of the boys. At the same time, they should stay close to your legs, if not hug them. A little. Not like a kid does a puppy. Like an appropriate camp counselor, or your favorite teacher from high school when you come back for a visit. (Bonobos shorts, for what it’s worth, have been engineered not to flare out at the sides and to fit you just close enough.)

Pay attention to length.

Length is part of tailoring, yes, but it’s a consideration that begins at the point of sale. There’s the obvious: you can always make them shorter — never longer (same with tighter and looser, respectively). Pro tip: I will sometimes buy pants and then have them cut into shorts, ensuring the perfect length. What’s office-appropriate length? I like about 4 inches above the knee, but really it’s a personal choice. Err on the longer side. At a certain point (usually a few inches below mid-thigh), your shorts can become less of a conversation piece than a conversation with HR.

Should I stay or should I cargo?

People have some very heavy opinions about things like cargoes and open-toed shoes. I don’t. Those who plant their flag in the former camp are thinking of the floppy, way-too-wide cargo shorts that guys wear inadvisable places (and that would be anywhere that isn’t your home or where there isn’t a game of pickup baseball).  As long as they are properly cut — and that means there is no room for a roller coaster in the legs — cargoes can be as refined as any other shorts. That said, keep your shit — gum, keys, pens, smokes — out of the pockets. Ironically, they are there for the look; they’re not purses for your thighs.

Do you work at a law firm?

Law firms, investment banks, and the like — these are not the places to test the boundaries of propriety. Casual Friday means you can skip the suit and tie, but the same rule applies for style as telling jokes: know your audience. Sorry: no shorts.

Can I wear shorts with a blazer?

I wouldn’t. You can, of course, do anything you want to. Wear a goddam pinata to the office. Hit your boss. But some things are just a matter of common sense. The blazer with shorts is too cutesy. It’s not impossible, but it’s a trick shot and not an easy one to pull off (if you insist, google and follow LeBron James’ example).

That’s enough!

Once you’ve taken the plunge, realize when to stop. Be like the Beatles and let it be, so to speak. The shorts are a statement (not a huge one, like a yell-whisper); feel free not to make things cacophonous by adding more. Maybe a belt, but that’s not even necessary. Skip the tie. Don’t you even reach for that damn hat. Less is more. And you’re missing the lower half of your pants, so that’s enough.

Shoe clues …

Unless you work on the set of a ’90s hip-hop video, avoid boots with shorts. It makes your legs look short and your feet look huge and it’s just plain inadvisable. Sneakers are less of a fashion crime and are more acceptable than ever, thanks to all the upscale minimalist brands out there, but I still say avoid. Go with something like loafers, oxfords, or maybe derby shoes with a short. It’s already a party down there; you don’t need to to start doing keg stands.

John Ortved is a New York City-based writer who watches altogether too much TV.  His articles and essays have appeared in the New Yorker, Vanity Fair, GQ, the New York Times and Vogue. You can twitter him @jortved.