Sky's Out, Thighs Out

Who Wears Short Shorts? Men Wear Short Shorts!

In the words of Sarasota Magazine editor Cooper Levey-Baker, "If the inseam is longer than 5.5 inches, GTFO." Here are five pairs we like.

By Megan McDonald June 22, 2022

The products listed here were independently selected by a member of the editorial staff. Should you choose to purchase a product through a link on this page, we may receive an affiliate commission.

Here's a photo of Paul Newman in his short-shorts in 1960. You know, just as an example.

Here's a photo of Paul Newman in his short shorts in 1960. You know, just as an example.

If it's true that history repeats itself, fashion is the first place to look for clues. Gen Z is dressing like it's the 1990s, Millennials are embracing their grandparents' style and men... well, men are wearing short shorts again.

@mikerocco7 Reply to @lindsaylikesfire Is this another Oops?😈. #5inchseam #outfitchange #DIYfashion #waitaminute #shouldervibe #single #dating #funnyy #fyp ♬ Wait a Minute! - WILLOW

As is so often the case, the trend started on TikTok (search #5inchinseam to see what we mean). Since then, celebs have jumped on board, too. Last year, a photo of This Is Us actor Milo Ventimiglia in a pair of teeny-weeny gym shorts—really, we're talking hotpants, here—went viral thanks to Ventimiglia's thigh-to-shorts ratio. Harry Styles, one of the most interesting dressers in the world right now, wore super-short jorts in a campaign for Gucci. And Irish actor Paul Mescal, late of the Hulu series Normal People—where he showed off a lot more than his thighs—set hearts aflutter when he rocked what The Guardian calls "budgie smugglers" while out and about.

Who knew showing so much thigh could be so liberating?

But while the trend feels fresh right now, short shorts for men were the norm for years. They debuted in the 1930s, albeit only for athletic activities, and grew in popularity—though not length—in the '40s, '50s and '60s.

The short shorts trend continued until the mid-1980s. Then, in 1984, Michael Jordan asked the NBA to sign off on longer shorts for play. That request—and its approval by the league—helped pave the way for the baggy, below-the-waist shorts trends of the '90s, which were also embraced by skaters and grunge and hip-hop artists. We saw a lot of boxers back then. There's even a term for the style: sagging.

But now short shorts are back. Men's calves can breathe, and it's their thighs' time to shine. We've rounded up five pairs we like, from a modest 7-inch inseam to a much shorter 4-inch one. As you shop, we invite you to remember these words from Sarasota Magazine editor-in-chief Cooper Levey-Baker, a longtime proponent of short shorts himself: "If the inseam is longer than 5.5 inches, GTFO."

Lululemon Bowline Short, 5" Stretch Ripstop

Lululemon Bowline Short, 5" Stretch Ripstop

Image: Lululemon

Bowline Short, 5" Stretch Ripstop, Lululemon Local

$78

140 University Town Center Drive, Sarasota

Casual and comfortable, these shorts from Lululemon are a great starting point. They come in several fun colors, have an easy elastic waistband, are waterproof and are perfect for working out or just wearing with a casual T-shirt.

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Chubbies "The Staples" 4-inch

Chubbies "The Staples" 4-inch

Image: Chubbies

Chubbies "The Staples" 4-inch 

$59.50

chubbiesshorts.com

On the other hand, if you want to go really short, Chubbies—which has been selling this style for years—offers a 4-inch option in stretch fabric and an elastic waist that still looks perfectly tailored. "Nothing will make your thighs look as good as these," the Chubbies team proclaims, and we suspect they may be right.

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Sun Farer 6" short from Island Pursuit

Sun Farer 6" short from Island Pursuit

Sun Farer 6" Short, Island Pursuit Local

$69.50

400 Madison Drive, Suite 206, Sarasota (941) 587-5316

Head out to St. Armands Circle to pick up a pair of these shorts from Sun Farer. They have a 6-inch inseam, an elastic waistband and drawstring, and plenty of pockets. In classic navy, they're ideal for a walk on the beach or a day on your boat.

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J.Crew's 5" stretch chino short

J.Crew's 5" stretch chino short

Image: J.Crew

5" Stretch Chino Short, J.Crew

$69.50

jcrew.com

These shorts might be the most formal of the bunch—made of chino, with just the right amount of stretch, they've got slanted pockets, a zip fly and belt loops. Pair them with Birks and a T-shirt or dress up your 'fit with a button down. We're partial to the Clay Sand color.

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Levi's 501® '93 Cut Off 7" Men's Shorts

501 '93 Cut Off 7" Men's Shorts, Levi's

$51.98

levi.com

We can't believe we're saying this, but jorts are on trend—just check out that Harry Styles Gucci ad we mentioned. If you don't want to splash out the cash for a luxury brand, Levi's makes an excellent alternative. These cut-offs, which have a 7-inch inseam, are an easy way to try out the trend—or, if you want to go shorter, cuff 'em as you see fit.

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