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By Barry Samaha, Ashley W. Simpson
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With heatwaves on the horizon and summer vacation days requested, it’s high time to invest in one of the best swim trunks. Going outside for a dip, surf, or simply to catch some sun is no excuse for letting your otherwise impeccable taste falter.
What does a swim trunk upgrade mean exactly? Well, we’re looking at styles that are so thoughtfully designed and well-cut that they can seamlessly double as shorts—ideal for the pool, of course, but also great when paired with a linen shirt or knit polo. The best swim trunks are both easygoing and considered—crafted with technical precision, durability, and quick-dry utility in mind.
Indeed, there are myriad options to choose from, a whole host of swim trunks of every conceivable length, color, and pattern. But if you’re looking for the standouts, the best of the best, the real-deal upgrades, check out the list below.
Todd Snyder Montauk Swim Shorts
Best Striped Swim Trunks
Of all the hamlets in the Hamptons, the go-to weekend destination for New Yorkers, Montauk is perhaps the coolest. It is the most chill and, quite frankly, the most fun. And capturing the essence of this seaside village are these (perfectly named) swim trunks from Todd Snyder.
Buy Now on Todd Snyder: $128
Saturdays Timothy Seersucker Swim Shorts
Best Seersucker Swim Trunks
Saturdays has been a favorite of downtown surfers and cool kids since 2009, which might explain why its take on seersucker—a preppy summer staple—feels so fresh. The six-inch inseam design is understated enough to wear around town, or just add an Oxford shirt and boat shoes and you’ve got Ivy style nailed.
Buy Now on Saturdays: $135
Loro Piana Mid-Length Swim Shorts
Best Stealth-Wealth Swim Trunks
See Also12 Pairs of 5-Inch Inseam Swim Trunks For Showing Extra Leg PoolsideThe 19 Best Swim Trunks for Men, According to ExpertsAmerican Eagle Outfitters Men's & Women's Clothing, Shoes & AccessoriesSwim Trunks | BatherThe textile whizzes at Loro Piana have, of course, a technical shell fabric that looks and feels like a million bucks—particularly in this refined shade of chocolate brown. They’re a pair of trunks that you can reach for whether you’re taking a dip or running errands on a scorching weekend.
Buy Now on Mr Porter: $415
Dandy Del Mar The Stirata Stretch Swim Shorts
Most Eye-Catching Swim Trunks
With a name like Dandy Del Mar, best believe that the brand offers the spiffiest styles for reclining by the ocean. The kinds of pieces that draw the eye and spark conversation. Indeed, it has a slew of swim trunks that reflects this sentiment, but the one that tops our list is this sleek option, cast in onyx-fleur print.
Buy Now on Dandy Del Mar: $109
Frescobol Carioca Sport Swim Shorts
Most Elegant Swim Trunks
Want something fun, not too serious, but still restrained and elegant? Look no further than Frescobol Carioca’s Rio de Janeiro–inspired swim shorts. Team with a linen shirt and espadrilles to double down on the aquatic vibe.
Buy Now on Frescobol Carioca: $225
Birdwell Nylon Board Short
Best OG Swim Trunks
If you are looking for a true surfer board short, Birdwell’s are a classic. Featuring a hardy design the company produced in the 1960s, this pair is made in Santa Ana, Calif., using nylon that’s been washed to achieve the sun-faded look and softness of well-worn chinos.
Buy Now on Amazon: $85
Le Sirenuse x Tombolo Limoncello Swim Trunks
Best Swim Trunks Collaboration
Le Sirenuse, the fashion pack’s preferred Amalfi Coast hideaway, produces a range of beachwear befitting its stylish clientele. It collaborated with Tombolo on a range of fuss-free resort attire, including this exceptionally soft swimsuit made from recycled plastic and emblazoned with the hotel’s signature sirens in a zesty shade of limoncello yellow.
Buy Now on Tombolo: $108
Derek Rose Maui Swim Shorts
Best Camp Swim Trunks
Swimwear is one of the few areas of a man’s wardrobe where cheekiness is welcomed. Derek Rose strikes just the right note of wink-wink with this all-over pattern of cherries. Thoughtful details such as a seamless mesh lining and a welted zip pocket deliver comfort and polish.
Buy Now on Derek Rose: $310
Orlebar Brown Bulldog Swim Shorts
Most Cinematic Swim Trunks
Orlebar Brown has developed a reputation for the definitive swim trunks (James Bond is a fan). The Bulldog is the British brand’s signature cut, with adjustable side tabs modeled off suit trousers for an ideal fit. Choose the light blue for a look that is equal parts confident and classic.
Buy Now on Orlebar Brown: $295
Dries Van Noten Patchwork Printed Swim Shorts
Best High-Fashion Swim Trunks
Many prints can be cloying, but Dries Van Noten’s are decidedly cool. The patchwork pattern will look great on a beach and even better at co*cktail hour with the addition of a white shirt and loafers.
Buy Now on Mytheresa: $251
CDLP Core Econyl Swim Shorts
Best Eco-Friendly Swim Trunks
These black swim shorts—clean, precise, the ultimate option for minimalists—are no-fuss and simply stylish. A bonus? They are sustainably crafted from Econyl, a premium regenerated nylon fiber made from fishing nets and nylon waste.
Buy Now on CDLP: $185
Anderson & Sheppard Ikat Swim Shorts
Most Princely Swim Trunks
Savile Row swim trunks? Yes, indeed. Royal warrant holder Anderson & Sheppard can help you suit up for your next dip in its expertly tailored trunks, like this pair in a quick-drying fabric featuring an artful ikat print.
Vilebrequin Flat Belt Stretch Swim Shorts
Best Belted Swim Trunks
French line Vilebrequin is known for its extremely high-quality swimwear. The yarn is sourced from Italy and woven in Spain; they’ll even replace the mesh liner if it rips. These bold tricolor swim shorts combine traditional red, white, and blue with a sleek flat buckle.
Buy Now on Vilebrequin: $280
Connolly Rosette Swimming Trunks
Best Floral Swim Trunks
British brand Connolly may be best known for its sumptuous leathers, but it also loans its luxurious touch to more beach-friendly wares. Its shell-pink swim trunks are made in Naples, featuring an elegant floral print and brass-tipped drawstrings.
Buy Now on Connolly: $210
The Merchant Fox Clipper Swim Shorts in Prince of Wales Check
Best Check Swim Trunks
Normally, anything with a Prince of Wales check spends summertime in storage. But not these gloriously patterned swim trunks from the Merchant Fox, which are further distinguished by tailored details including side adjusters and a six-piece waistband.
Authors
Barry Samaha
Senior Commerce Editor
Barry Samaha is the senior commerce editor at Robb Report, where he oversees all things shopping. Previously, he was an editor at Esquire, Harper's Bazaar, Surface, and WWD, along with overseeing…
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Ashley W. Simpson
Ashley W. Simpson is a writer from upcountry Maui, Hawaii who has covered art, visual identity, culture and public policy for W, Interview, Vogue, AnOther and Esquire. She splits her time between…
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