41 Dos and Don’ts for Getting Dressed for the Office

In a work environment, intentionality is key. Criales-Unzueta avoids outfits that feel overly casual, an inclination he credits partially to growing up in Bolivia: “Latinos in general have a very specific concept of elegance,” he explains. He prefers a hard-bottomed boot to a rubber-soled sneaker, balances out casual pieces (such as a concert tee) with dressier pants, and reckons he’s never worn a hoodie to the office—or, for that matter, a pair of short shorts, as much as he appreciates them. “I wear short shorts all the time to work out [or] on the weekends,” he says, “but I’ve never, like, shown a thigh at the office.”

Do not, under any circumstances, buy a shirt “designed to be worn untucked.”

As a general rule of thumb, most dress shirts are cut a little longer to stay politely lodged beneath your pants. Wear them as designed. But if your shirttails naturally hover an inch or two below your waistline, feel free to let ’em fly.

Fit is everything.

Many of our interviewees say their coworkers don’t seem to know how their clothes should actually fit. Typically, especially in tech and finance, they are too small and tight. “You can still carry yourself with confidence if your quads don’t look like someone put a 10-pound honey glazed ham in a tube sock—I swear,” says Byron, the tech sales executive. Meanwhile, at the high school where he teaches English, Bret says many of his colleagues veer too far in the other direction, shrouding themselves in shapeless, blousy shirts and baggy slacks. “Everything they wear is too wide and too long,” he says, “and not in a fun way.”

Fashion trends, of course, cycle between slimmer and looser silhouettes every few years. But the middle ground—that is, properly-fitting clothes—is enduringly flattering, which is precisely what you should be aiming for with your office wear. Just look, for instance, at these two older Italian gentlemen that Byron clocked on a recent trip to the island of Favignana: their clothes are neither sprayed on nor falling off, they’re comfortable enough to ride bicycles in, and they look as sharp in 2024 as they would’ve in 1953. That’s real style.

Take care when complimenting a coworker’s outfit.

The barriers to dressing up nicely for work are myriad: limited time for ironing in the morning, sweaty commutes, etc. But self-consciousness about taking a big swing on a big, buttoned-up fit shouldn’t be one of them. One way to look out for your fellow colleagues stepping out on a sartorial ledge? Avoid paying them undue attention or dropping stray commentary, such as the dreaded (if jokey) “Ooh, got a job interview today?” when you see them in a suit. If a coworker looks more dressed up than usual, skip the “Well, you look awfully fancy today” and instead opt for a less-loaded compliment. A simple “I love your outfit” never hurt.

Additional contributions by: Eileen Cartter, Nick Catucci, Yang-Yi Goh, Avidan Grossman, Samuel Hine, Noah Johnson, Martin Mulkeen, Cassandra Pintro, and Cam Wolf.