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4 Chic Ways to Wear Shorts

Here’s your cheat sheet to surviving the last dog days of summer in style.

Designer Shorts for Men Photo: Courtesy

Shorts are undeniably a casual look, and sometimes it can feel impossible to style them in a way that feels grown-up and clean-cut without becoming boring. And while many of our favorite brands have begun to roll out sumptuous knits and wool trousers we can’t wait to slip on for fall, considering the inescapable scorching-hot weather outside, shorts are going to be a weekend essential for at least a few more weeks. So, get yourself through the last of these dog days of summer by refreshing your shorts wardrobe—not only will it make dressing when the temperatures hit triple digits a snap, but you’ll also be thanking yourself for investing in a fresh pair when you head out on that tropical vacation once the seasons change.

The following four styles run the gamut from edgy to preppy—but all are far from feeling boyish or like you’re channeling your dad on vacation. And, they’re guaranteed to keep you looking and feeling cool during the last of those hot August nights.


Gucci’s cotton shorts ($650) display the brand’s penchant for playful, slightly subversive pieces at its finest. Though they look like plain khaki at first glance, a second look reveals a personality-packed detail: Tiny golden bees, one of the icons of the Gucci Garden, are embroidered throughout. The shorts’ sharply tailored cuts keep them feeling mature, so pair them with a blue button-up shown here to keep things formal (though we’d suggest sticking with traditional loafers). Or, let a T-shirt hang loose over the top to dress them down.

Gucci Shorts

Gucci Shorts  Photo: Courtesy Gucci



Made of lightweight (read: ultra-cool) nylon, Theory’s reflective print shorts ($185) are the ultimate easygoing late-summer short. The minimal style will slot right in with the rest of your weekend wardrobe, and thanks to their water-resistant construction, they’re the ideal pool-party companion when you can’t get away with wearing a pair of trunks all day. Wear them with crisp whites for a casual day out, or throw on a bolder shirt—a patterned camp-color style would work nicely—for alfresco dinners.

Theory Shorts

Theory Shorts  Photo: Courtesy Theory


Despite their undeniably bold yellow hue, Dunhill’s twill Bermuda shorts ($195) are the type of summer essential that will be in your closet for the next decade. They are made of comfortable stretch cotton, but their sharp darts and cuffed hems keep them from looking overly relaxed. Finish this look with a relaxed white tunic-style shirt and your favorite sandals for a sophisticated vacation vibe.

Dunhill Shorts

Dunhill Shorts  Photo: Courtesy Dunhill

Thom Browne

A cropped version of your favorite sharp suit pants, these shorts ($945) from Thom Browne are a playful take on summer tailoring. They are cut from wool twill, giving them that familiar suit-style structure, but Browne’s signature red, white, and blue stripes running down the leg adds a subversive, sporty twist. They’ll pair nicely with a tucked-in white shirt for a low-key summer wedding or will work with a lightweight black sweater once the temperature finally starts to break.

Thom Browne Shorts

Thom Browne Shorts  Photo: Courtesy Matches Fashion

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