It’s now consistently warm enough in Brooklyn to retire my leather jacket and flannels. My selvedge denim will soon follow them into storage. Shorts weather has arrived—and with it, two important implications. First, you can no longer get away with skipping leg day. Second, you must invest in flattering shorts and tweak your wardrobe to complement them.
Shorts are neither as dressy as chinos nor as versatile as jeans. For all their comfort and convenience, they’re trickier to pull off. A few caveats for looking natty in shorts: Unless you’re going swimming, skip the flip-flops. This ain’t the rec room at Camp Chippewa, bud. Avoid exterior pockets, keeping in mind that nobody’s gotten laid in cargo shorts since Vietnam. Bermudians, those tropical Anglophiles, like to don shorts with blazers and ties. Far be it from me to disparage other cultures, but I’ll offer this: whoever sets fashion standards in Bermuda needs to lay off the Gosling’s rum.
From classic khaki to breezy seersucker and jaunty pastels, these are the sickest shorts for summer 2025. Pair them with a guayabera, vintage sunglasses, and Amberjack loafers for a complete summer playboy aesthetic. And for God’s sake, hit the squat rack once or twice.
Photo via Vineyard Vines
Vineyard Vines – Seersucker Breaker Shorts
Shep and Ian Murray, brothers from a family of New England haberdashers, left high-octane finance jobs in Manhattan to live on Martha’s Vineyard under the pretext of building a clothing company. They began by selling ties and bowties—pastel-colored and playfully patterned with motifs like martini glasses, fish, and lighthouses—straight off their boat in Edgartown Harbor. Since then, Vineyard Vines has expanded its product line to include blazers, button-downs, and all manner of luxury attire with preppy flair.
Seersucker has long been associated with Southern aristocrats, but you don’t need to be a Charleston boulevardier to pull it off. Woven from lightweight cotton, the Seersucker Breaker Shorts are breathable and light as a dream, perfect for staying cool on even the hottest August days. The besom pockets secured with polished brown acetate buttons add dressy flair to an otherwise laid-back summer staple.
Photo via Huckberry
Flint & Tinder – Cotton Linen Shorts
Echoing the origins of Ralph Lauren, Flint & Tinder set out to honor classic American attire—from the denim of ranchers to the cotton-twill jackets of factory hands. They manufacture most of their clothing domestically, a commitment aligned with their revivalist approach to the American cut-and-sew industry. Huckberry, a nonpareil online purveyor of men’s clothing, acquired Flint & Tinder in 2012, helping the brand expand into leatherwear and footwear.
Crafted from a blend of cotton and linen, the Cotton Linen Shorts are feather-light but sturdier than pure linen. I favor them in off-white, a color that looks sharp with a button-down, a guayabera, or a pastel polo. A discreet change pocket tucked beneath the waistband secures coins, cufflinks, or ticket stubs. When I wear these shorts on a summer evening, I light a cigar and imagine I’m a Mediterranean shipping magnate.
Photo via B. Draddy
B. Draddy – Big Daddy Shorts
Based in New York City, B. Draddy designs upscale golf attire. Personally, I don’t give a whit about golf beyond Happy Gilmore fandom, but I admire B. Draddy’s unapologetically preppy ethos and meticulous craftsmanship. The Big Daddy Shorts are made from Peruvian Pima cotton, the crème de la crème of cotton textiles, and come in rakish hues like Nantucket red, crushed mint, and sky blue. Nota bene: avoid wearing more than one pastel piece per outfit, lest you resemble a walking Easter egg. Pair brightly colored shorts with a subdued white polo or crisp button-down. Conversely, if your shirt is a loud color, stick to neutral khaki shorts.
Photo via Bonobos
Bonobos – The Chino Short 2.0
Bonobos founders Andy Dunn and Brian Spaly were fed up with the ill-fitting, balloon-legged chinos in department stores, so they set out to design trousers and shorts that were tailored, comfortable, and durable. Khaki shorts are the linchpin of my summer wardrobe, and Bonobos makes the best pair I’ve found. With pockets spacious enough to carry your phone and wallet without bulging, the inseam hits just above the kneecap. Bonobos’ cut flatters the legs without veering into obnoxiously tight territory—unlike shorts that recall a cheap hotel: cramped, with no ballroom.
Photo via Smith + Rogue
Smith + Rogue – M’s Oeste Shorts
Born in Montana cattle country, Smith + Rogue crafts genuine cowboy gear. This is no transnational conglomerate cashing in on yuppies’ eagerness to cosplay Yellowstone—it’s honest workwear worn by ranchers from Bozeman to Cheyenne. Accordingly, Smith + Rogue clothes are built to last, with no corners cut on materials or craftsmanship. In smart, neutral shades like stone, black, and chocolate, the M’s Oeste Shorts feature a water-resistant finish and a loop concealed within the pocket to secure your keys while hiking or fishing. They’re less dressy than other shorts on this list, but they’re my go-to when I’m throwing on a T-shirt and sneakers.
