okay but how do i wear it?

How to Look Good in Bermuda Shorts

Julia Roberts wears long shorts in Pretty Woman — The Strategist reviews the current Bermuda Short trend.
Julia Roberts, giving a master class on long shorts.

“Long shorts are stylish again,” my mother told me last weekend. Then, dreamily, “I love long shorts.”

“Long shorts” is a euphemism for Bermuda shorts, an article of clothing that became popular in the ’40s and then again in the ’90s. These truncated jeans, or extended shorts, are, as my mother wisely announced, making a comeback: Brands like the Brooklyn-mom-favorite Caron Callahan, playful French label Bless, and even the Reformation have recently released updated takes on the style. And the beautiful people have been photographed giving them a spin: This Instagram of model Paloma Elsesser is what piqued my interest in the style in the first place. This picture of Man Repeller editor-in-chief Leandra Medine didn’t hurt, either.

In theory, I like Bermuda shorts: The length makes them appropriate for work and could solve the problem of how to dress comfortably for both freezing offices and sweltering commutes. But let’s address the obvious: Worn incorrectly, the things can be ugly or unflattering or both. The cutoff point draws extra attention to the thigh, an area some of us take great sartorial pains to hide. But as with most things, if styled properly, this does not have to be the case. Since I haven’t worn a long short since middle school (denim, Abercrombie & Fitch), I turned to the designer Caron Callahan, the Cut’s fashion news writer Emilia Petrarca, and the Cut’s fashion editor Lindsay Peoples Wagner, all of whom gave me some helpful pointers on how to wear these strange in-betweenies.

Accentuate your waist and ankles

“If your longer short is slightly loose,” Callahan told me, “it’ll look great belted with an oxford shirt tucked into them, to show off your silhouette. As for shoes, I’d go with something a little more covered up, like an espadrille.” Petrarca suggested a kitten heel, or sandal that wraps around your ankles, “so your legs look longer, and not like SpongeBob SquarePants.”

Mother Denim Bermuda Prep Short
$178 at Garmentory
The Air Oxford Shirt
$58 at Everlane
Original Dali Espadrille Slip-On
$42 at Nordstrom
Esparto Linen Wedge
$35 at Spring

Dress them up

“Another way to go is to dress it up,” says Callahan. “When I think of longer shorts, I think of Lauren Hutton in American Gigolo. Wear them with a nice blazer and a blouse.”

Bermuda Short in Stretch Linen
$80 at J.Crew
The Italian GoWeave Classic Blazer
$125 at Everlane
The Silk Short Sleeve Square Shirt
$88 at Everlane

Make a suit

“Or treat them like trousers, and wear them with a matching jacket, like a little summer suit,” says Callahan. “This look would look great with a pair of oxfords.”

Just Female Amalie Houndstooth Shorts
$113 at Need Supply
Just Female Amalie Blazer in Houndstooth
$208 at Need Supply
The Modern Oxford
$168 at Everlane

Go loose

Petrarca feels that looser is better, when it comes to long shorts. “I have a pair of green ones which hang at my hip,” she says. “I roll up the hem to make them a bit shorter, and wear them either with a tight T-shirt or a blouse tucked into the front. If you go loose on loose, you’ll look like you’re at camp.” But, she warns, don’t wear a top that’s too buttoned up — otherwise, it’ll have a militant effect. “Try a floaty Nili Lotan top,” she recommends.

Caron Callahan Stewart Short
$265 at Caron Callahan
Cresta Trail Bermuda Shorts
$55 at L.L. Bean
Dickies 1922 x Opening Ceremony Painter’s Shorts
$140 at Opening Ceremony
Miles Gathered Yoke Blouse
$275 at Nordstrom

And if you’re going to go tight …

“Kim Kardashian, who often wears a tight Bermuda short, does not look good in them to me because of how she styles them — heels and a bodysuit, which makes her look like a bad workout video from the ’80s,” says Wagner. “But the model Paloma Elsesser wears tight Bermuda shorts and makes them look amazing — she wears them with dad sneakers and a T-shirt, or a printed loose shirt and Adidas slides. Her tomboy aesthetic really compliments them.”

Levi’s Women’s Bermuda Shorts
$28 at Amazon
Adidas Originals 3 Stripes Ringer Tee
$35 at Urban Outfitters
Fila Disruptor 2
$70 at Urban Outfitters
Adidas Adilette Comfort Slide Sandal
$25 at Nordstrom Rack

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How to Look Good in Bermuda Shorts