Why Don’t More People Wear Shorts to Work?

As people continue to push the boundaries of traditional office wear, shorts can still feel like a risky choice. Our critic explains why that is, and offers a few styling tips.

To give you a … well, short answer: not at all. Shorts are often longer than skirts these days and often more conservative. There is no reason a woman shouldn’t wear them to the office. It’s a little more complicated for men, even considering the success of Thom Browne, because of our more complicated feelings about men’s legs. But that’s a whole different story.

If there’s any hesitancy about women, work and shorts, I think it comes from our deep-seated associations with the garment, which generally have to do with summer, weekends and childhood. Shorts are what we wear when we aren’t at work, so it can seem uncomfortable, or even subversive, to wear them in the office.

In our psychographic wardrobe, they represent leisure, and sports. Opting to wear them in a professional capacity for anyone who isn’t an athlete is as much a mental choice as a fashion decision. Which may be why they seem to be the last frontier of dress code revisionism. We’ve abandoned the tie, accepted the hoodie, but shorts … well. The jury is still out.

In practical terms, however, there is no reason not to wear shorts to work — or at least a certain style of shorts. As with any garment, it’s the kind of shorts you wear that matter and how you dress them up.

Very short shorts, no matter how tailored or office appropriate the fabric, should be avoided, just like very short skirts. So should rompers. (No one will take you seriously in something called a romper.) So should anything resembling bike shorts. Demi Moore wore them once with a brocade skirt to the Oscars, but the resulting derision is all you really need to remember about that.

Instead, opt for shorts that reach almost to the knees or fall below the knee, so they have more in common with their sartorial ancestor, short pants (or at least capri pants), than, say, underwear. Not to mention Bermuda shorts or walking shorts. Then, said the stylist Karla Welch when I asked for her recommendations, add a T-shirt (tucked in and belted), a blazer and “conservative shoes”: platform loafers, say, or kitten heels or even pumps. Another option: an oversize button-up shirt.

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