How to Wear Shorts (and Look Good Doing It)

May 22 2025
How to Wear Shorts (and Look Good Doing It)
As soon as the temperatures start to rise in late spring, I start thinking about idyllic warm-weather outfits for summer vacations still months away. Having just come back from Australia, where the Sydneysiders were characteristically showing off their love of shorts, I returned to New York ready to figure out the chicest way to show off a little (or a lot of) leg. In this edition of Addressed, we’re answering the eternal question of how to wear shorts—and look good doing it.

When talking about shorts, we first have to deal with the issue of length. Last year I declared that the nu-metal short—slightly baggy with hems right below the knee—the fit of the summer, and while looking through the recent collections, it seems that designers have agreed to keep it going for another season. That’s great news for me; I wasn’t ready to give them up. However, they aren’t the only contenders; two years after Miuccia Prada proposed the idea that panties are acceptable bottoms to wear out in the world, micro shorts (their slightly more modest counterpart) are coming in strong. These opposing ideas—long, baggy, and masculine coded or extra short and literally inspired by women’s underwear—actually make sense together. The times call for decisive ideas and decisive style; now is not the moment for wishy-washy, half-baked concoctions. We’re going all or nothing.

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