Men wear short shorts. Maybe not all men, but for summer outfits this season, trend setters, Hollywood heartthrobs, and svelte models parading down designer spring 2024 runway collections all donned the thigh-grazing shorts style more than we’ve seen in recent years. But the real question for most men — regardless of their stance on the shorts length debate — is how to style summer shorts to look on-trend, flatter their form, and feel comfortable and confident while showing off those gams.

The reason for this men’s shorts conundrum comes down to the attention a leggy look can attract. Back in 2021, actor Milo Ventimiglia almost broke the internet when paparazzi snapped a shot of him in a parking lot in five-inch athletic shorts, Converse high-top sneakers, and a heavy-metal concert tee with the sleeves cuffed up to a muscle tank length. While it might not sound controversial, the “This Is Us” star’s muscular thighs naturally pushed up the shorts to show more skin than his fans were used to seeing — and the ladies went gaga. However, not all men desire that kind of ogling, yet, the trend seems to have continued in the mainstream as short hems continues to shorten.

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Short shorts outfits are not new in menswear. Sean Connery’s James Bond made the short short and Cuban shirt 007’s uniform in “Thunderball” back in 1965. In the 1980s, Hollywood Hunk Burt Reynolds effortlessly sported the five-inch short in several episodes of “Magnum P.I.” Meanwhile, Harrison Ford’s navy blue knit sweater and short shorts with brown boat shoes in 1982 Cannes Film Festival happens to be one of the most referenced men’s summer shorts outfits inspirations. Similarly, John F. Kennedy Jr.’s most buzzed-about photos from his youth features the late son of Jacqueline Kennedy sporting khaki short shorts with nothing on but a shark tooth necklace.

Not all summer shorts outfits for men have to show so much skin. Several spring 2024 menswear runway collection featured shorts that ran the gambit of lengths, especially at Louis Vuitton’s show with shorts that hit mid-thigh, just above the knee, and right below the knee. Dries Van Noten, Sacai, and other menswear collections featured a more airy, pleated Bermuda short that when styled correctly, can look modern and less of a dad-style fashion faux-pas.

When it comes to selecting the right bottoms for your best men’s summer shorts outfits this season, there are a few things to consider. First, your height can play a major factor here. Short kings should go no longer than a short that hits right above the knee or your risk appearing even shorter. While men of a certain height — such as Jacob Elordi’s six-foot-five statuesque physique — can wear a short with suiting separates, you want to make sure not to skip leg day or twig-like legs might look less than favorable.

In the spring 2024 menswear collections, the full styling equation plays a major part in discovering the right shorts for your outfit of the day. A combat boot or moto boot paired with long socks and above-the-knee short looks fresh when the ensemble is topped off with a top coat of a longer length, as seen on actor Pedro Pascal at the 2023 Met Gala. If you spied shorter shorts at Prada, Gucci, and Dior menswear spring shows, you would have noticed a wider leg opening (usually with pleated darts). This silhouette creates a nice proportion with an oversized button down with less of a look-at-me effect.

This year, actor Paul Mescal showed that confidence is key to any short length, whether he’s wearing a casual athletic outfit with short shorts or while attending Gucci’s spring 2025 menswear show in boxer shorts with a breezy blue button-down shirt, white men’s dress socks, and the Italian fashion house’s iconic Horsebit loafers — the man really sold us on this ‘fit.

Whichever way you decide to embrace shorts this summer, whether it’s channeling Ralph Lauren’s gray turtleneck sweater and white short attire from the ’70s that was used on recent runway show invitations for his spring collection or rocking a ’90s Giorgio Armani shorts outfit of classic tee tucked neatly into knee-length navy pleated shorts, accessorized with a simply stylish belt and brown loafer, there’s a way for guys to style out summer shorts outfits for all lengths of comfort.

To help you out, take some men’s summer outfit inspiration below, inspired by street style savants who aced the shorts style game.

Summer Shorts Matching Set Outfit for Men

Getty Images

When in doubt, go for the total look. This minimalist Dior runway look in blue looks effortlessly cool for any occasion during the hottest days of summer when paired with textural loafers and a sleek sock situation. A classic men’s watch and flattering shades are the ideal finishing touches.

Todd Snyder Cropped Terry Cabana Polo Shirt

$158

Buy Now at Todd Snyder

Lululemon Bowline Short 5″ Stretch Ripstop

$78

Buy Now at lululemon

Citizen Promaster Fujitsubo Super Titanium Watch

$796 $995 20% off

Buy Now at citizen

Skims Sport Crew Socks

$10

Buy Now at skims

Alo Recovery Mode Sneakers

$185

Buy Now at Alo Yoga

Lululemon Wanderlust Backpack Mini 14L

$128

Buy Now at lululemon

Tag Heuer Vingt Sept Sunglasses

$540

Buy Now at Tag Heuer

Short Shorts Outfit for Men

Getty Images

A good rule of thumb when sporting the short shorts summer outfits style is to keep proprotion in mind. Let your top have a relaxed, oversized fit while your muscular legs catch some sun. Complete the look with fresh white socks and a breathable shoe, such as fisherman sandals.

Ralph Lauren Cotton Chino Ball Cap

$49.50

Buy Now at Ralph Lauren

Proper Cloth The Aveiro Wide Stripe Linen Shirt

$130

Buy Now at Proper Cloth

Bulova Classic Necklace

$250

Buy Now at Bulova

Buck Mason Herringbone Twill Larsen Short

$128

Buy Now at Buck Mason

Bombas Men’s Modern Rib Calf Socks

$16

Buy Now at Bombas

Allen Edmonds Monaco Sandals

$229 $295 22% off

Buy Now at allen edmonds

Bleu De Chauffe Bazar Tote

$256.66

Buy Now at Bleu De Chauffe

Short Suit Outfit for Men

Getty Images

The short suit can be a tricky trend for most men to comprehend. For those who favor the bold, your go-to luxury accessories pack of punch of style that’ll give you the stylish swagger of a dapper man and feel like like a little boy in summer formal wear. Swap your button down for a classic white ribbed tank to show some skin around your neckline and flash a little touch of a thin chain necklace.

Banana Republic Corcoran European Linen Suit Jacket

$400

Buy Now at banana Republic

Mejuri Flat Curb Chain Necklance

$548

Buy Now at mejuri

Skims Cotton Men’s Rib Tank

$24

Buy Now at skims

Banana Republic Linen Pleated Pull-On Short

$80

Buy Now at banana Republic

Sunspel Cotton Socks

$32

Buy Now at sunspel

Gucci Men’s Jordaan Loafers

$920

Buy Now at gucci

Citizen Rolan Watch

$300 $375 20% off

Buy Now at Citizen

Celine Homme Triomphe Leather-Trimmed Monogrammed Coated-Canvas Pouch

$650

Buy Now at Mr. Porter

Meet the Author

Adam Mansuroglu is the Director of Commerce for Footwear News and WWD, overseeing strategy for shopping content on both brands, along with writing and editing shopping guides, product reviews, and shopping trend stories across fashion, beauty, home and lifestyle product categories for men and women. Prior to his current role, Mansuroglu was a fashion editor and stylist at Cosmopolitan Magazine, Style Editor at BestProducts.com, and Senior Style and Gear Editor at Men’s Health Magazine. Mansuroglu has been tapped as a shopping expert for editorial websites such as Wirecutter, and his writing has also appeared in Out Magazine, Esquire and other publications.

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The Best Summer Shorts Outfits to Flatter Any Man’s Form With Cool Style

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