Shorts are polarizing. Yes, they’re a summer staple. But no, not everyone thinks they look good in them. Fear of camel toe and constant wedgies aside, shorts are necessary on a hot, humid summer day. And they can be versatile: A beat-up pair of Levi’s cutoffs always manages to look cool, while a fancy high-waisted style can be as polished as an A-line or pencil skirt — with less thigh chafing. And that doesn’t even count casual walking-the-dog shorts and any others in between.
We recently went deep on the resurgent Bermuda-shorts trend, so for those we’ll direct you over here. For all other shorts, we asked a handful of style editors about their favorites, and then matched those with some look-alikes.
Anna Gray, writer, editor, and creator of the Things I Would Buy If I Didn’t Have to Pay Rent newsletter, owns just one pair of shorts: a cutoff version of Jesse Kamm’s popular Sailor pant. These have the same button-fly and waistline as the Sailor, plus an optional double-cuff that can be rolled down for a bit more length. “They do all the same form-hugging as the full-leg edition. In less descriptive terms, they make my butt look cute,” Gray says. “A loose button-down shirt tied in front, maybe Hawaiian print, with these shorts is a real cool look.” Because the Kamms aren’t widely available this season, we’re going to point you to Everlane’s high-rise twill shorts, which look nearly identical to the Kamms and come in army green, yellow, white, black, and this tangerine orange.
These high-rise cotton-gabardine shorts by Masscob have a similar chinolike structure, in a similar lightweight material.
Or for a paint-splattered artist-in-the-studio look, these chino-style shorts by Sanctuary mimic the high rise of the Kamms.
And if you just want the damn Kamms: They’re still available in this crisp white color called “salt.”
A summertime staple for Elana Fishman, style editor at “Page Six,” is this Madewell style. “My body physically rejects any clothing that isn’t high-waisted, so these navel-grazing denim boy shorts are my summertime staple.“With their nearly 11-inch rise, they almost hit my belly button — I have a freakishly long torso — and they’ve got just a touch of stretch, which means you can sit in them without suffocating.” She has them in black, but we also dig the faded blue of this pair.
If you prefer cutoffs to be nearly boob-grazing, this heavily frayed Agolde pair has a 12.25-inch rise that Caroline Maguire, fashion director at Shopbop, swears by. “I love a great high-waisted denim short. The higher the rise, the better,” Maguire says. She pairs these with everything from a tee to a crop top, or for a statement look, a button-front dress, layered on top and tucking halfway into the shorts.
Again, we can’t help but also recommend Everlane’s new high-waisted denim shorts.
Paige also makes an excellent high-rise washed denim pair of shorts (comes in white denim or regular blue denim, too).
“These high-waisted, trouserlike shorts are work-appropriate, but still look professional and polished during the summer heat,” says Chriselle Lim, entrepreneur and founder of CINCstudios. Pair with a white, crisp button-up and pumps, Lim suggests. She also recently designed her own shorts (with J.O.A. and Shopbop), dubbed the Paper Bag Waist Shorts. “I also love the elegant yet playful ruffles, plus the extra-high-rise waist is super flattering,” Lim says.
Albeit a bit shorter than the long ones she wears, these have a very Sloane–from–Ferris Bueller’s Day Off feel.
These on-sale Derek Lam shorts have a very cool Great Gatsby vibe.
But we also like these swingy shorts, at a much more accessible price point.
These very ladylike, very heavily discounted, Diane von Furstenberg shorts in the Abel cross-check would easily work in the office or on the weekend.
Levi’s can’t really be beat in this category. Maria Dueñas-Jacobs, director of brand development at Stitch Fix, likes to get hers from vintage shop What Goes Around Comes Around because they tailor them precisely. But the quest for excellent jorts is ongoing: “Like jeans, I can never get enough of, or stop searching for the next, great cutoff denim shorts,” she says. There are myriad styles on sale at Spring.
The Wedgie Fit jean, converted into a short.
Or, try a playful pair in an ultralight wash with frayed hems, colorful embroidery, and a removed back pocket, like this pair recommended by Karla Martinez de Salas, editor-in-chief of Vogue Mexico. “I wear these all summer; at the beach, at least, as Mexico isn’t really a shorts city.” She adds, “These fit well, and you can dress them up or down.”
For a high-rise style that’s got some stealth flexibility, and is available in a wide range of sizes, consider this pair of cutoffs from Good American, Khloé Kardashian’s denim brand, suggests Katie Sturino, founder of the 12ish Style, a blog covering size-12-to-18 fashion. “They have stretch, but they don’t look like they have stretch, you know?” Sturino recommends sizing up with these, “but I love the fact that they cover an inclusive size range,” she underscores. “Good American is the first brand that allows plus-size girls to participate in some classic summer cutoff styles; it’s the first time I have had ‘cool’-looking denim cutoffs.”
Skirts are far preferable to Michelle Lee, editor-in-chief of Allure, “so if I’m going to be in shorts, I want cozy,” Lee says. “These are soft fleece with an elastic waist, but still cute enough to look like you put in some effort.” The retro-tinged striping is a slight upgrade on the sort of shorts easily available at your local Modell’s or Dick’s. “I’ve bought those generic, cheap, institutional high-school gym shorts before from sporting-goods stores, which aren’t bad, but I love the ’70s stripe on these so much more.”
A full range of sizes aren’t available in Lee’s favorite shorts, but these John Galt shorts are similarly retro and stripy.
And these on-sale Cosabella shorts have a cozy, vintage gym-short look to them.
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best women’s jeans, rolling luggage, pillows for side sleepers, ultra-flattering pants, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.
Every editorial product is independently selected. If you buy something through our links, New York may earn an affiliate commission.