Men's Lifestyle July 24, 2026 0 Comments

Unlock the Secret Moves to Rock Any Men’s Swimsuit This Summer—Avoid These Rookie Mistakes!

Here’s a life hack that’s as simple as it is oddly profound: always pack a swimsuit. Sounds cliché, right? But hear me out. It’s not just about having the gear for a spontaneous dip—it’s about embracing that little spark of optimism, that unshakeable belief that, no matter where you are or what you’re doing, there’s a chance you’ll stumble upon that perfect pool, beach, or hidden cove begging for you to jump in. Now, the real kicker? Choosing the right swimsuit isn’t just a matter of style—it’s the all-important foundation for literally putting yourself out there, nakedly confident (okay, almost naked). Whether you’re a swim-trunk traditionalist, a board-short surfer, or toeing the line with something a bit more tailored, this guide breaks down the essentials so you can not only look good but feel unstoppable when you hit the water—or just pretend you might. Ready to dive in without all the sweat over what to wear? Let’s make swimwear your new secret weapon. LEARN MORE

6 min read

Years ago, I received a piece of advice from a colleague here at Esquire that doubled as a sort of overarching approach to life: Always pack a swimsuit. No matter where you’re going, what you’re doing, or what time of year it is, pack a swimsuit. On the practical side, it’s a good idea because a swimsuit doesn’t take up much space and putting one on is simpler than dealing with a public-nudity charge. But there’s also a philosophical implication, because packing a swimsuit isn’t just being prepared; it’s a way of tapping into the optimistic part of yourself that believes, however unlikely it seems, that you might just need it.

Because going for a swim—in the pool, in the ocean, in some magical cove at the end of a hiking trail—is a genuine pleasure. You float. You splash. You dive. It’s a freakin’ lovely experience.

What can be less lovely, though, is picking the swimsuit to wear while you’re doing all this. When a single item of clothing is the only thing you’re wearing, it has to do all the work, stylistically speaking. For those of us who care about the wide world of menswear, that can be anxiety inducing. Throw a bunch of different options into the mix, all with their own pros and cons, and one would be forgiven for feeling a minor sense of dread when choosing a new suit.

The first thing to remember here is that sense of optimism I mentioned earlier. The point is swimming, soaking, wading—enjoying yourself. That’s what really matters, and pretty much no one else on the beach or the pool deck is going to give a damn what you’re wearing (so long as you’re decent). But looking good can go a long way toward feeling good, so picking the swimsuit that makes you the most comfortable is a worthwhile endeavor. This guide will help you do that, breaking down the core styles to know now, where to get them, how to wear them, and more. Let’s get into it.

The Classic Swim Trunk

©AMC/courtesy Everett Collection

Lead image: John F. Kennedy Jr. at Hyannis Beach in 1980. Above: Of course Don Draper was a classic swim-trunk guy.

The concept of the quintessential swimsuit has shifted drastically over the years. At one point, it was pretty common to see a guy in a singlet that covered his entire torso doing laps at the pool or splashing around in the ocean. But the classic swim trunk is what most folks tend to think of when they think men’s swimsuit these days. It’s usually got an elasticized waist with a built-in drawstring, a liner, and a couple of hip pockets complemented by a single back pocket, though the configuration of those features can shift from trunk to trunk. Inseams tend to be five, seven, or nine inches. (Seven is a good middle-of-the-road length these days.) It’s basically an easygoing pair of shorts converted to be water-friendly with the use of quick-drying fabrics—polyamide and nylon are favorites—and mesh pocket bags that let the water drain out with ease.

You can find options in pretty much every pattern and color you can imagine, from a list of brands so long that it’s pointless to try to name them all. That said, we can call out a few Esquire favorites. Patagonia Baggies are an easy go-to that don’t cost a lot and can pull double duty as shorts (so long as you’re comfortable with the liner). Specialists like Fair Harbor, Onia, and Bather make great trunks, as do not-crazy-expensive fashion brands like Buck Mason and Todd Snyder. And if you want to get fancy, you could always opt for the St. Tropez–inspired Vilebrequin, the Rio de Janeiro–inspired Frescobol Carioca, or major fashion houses like Loro Piana, Brunello Cucinelli, and Tom Ford.

Wear it with: Anything you like, really. The classic trunk is a style chameleon. But it really shines with chilled-out summer basics like plain tees, loose camp-collar shirts, canvas sneakers, and Birkenstocks.

Patagonia Baggies 5” Shorts

Credit: Patagonia

Todd Snyder Montauk Swim Trunks

Credit: Todd Snyder

Vilebrequin Coral Mandala Swim Trunks

The Tailored Swim Trunk

Archivio Cameraphoto Epoche//Getty Images

Paul Newman at the Lido in Venice in 1963.

If the classic trunk doesn’t feel sartorial enough for you, there’s always the tailored swim trunk. Finished with a set waistband instead of an elastic one, it’s cut slimmer and shorter so you can prove to everyone at the pool that you didn’t skip leg day—or any other gym day—during the winter and spring. As with the classic trunk, you’re usually getting a couple pockets, which is all the better to mimic the look and feel of regular shorts. But don’t bank on a liner. And don’t get overexcited at the prospect of loud, colorful, overtly “beachy” prints and patterns either. The tailored swim trunk has carved out a space in the world by aiming for a certain degree of sophistication, so solid colors and classic patterns like seersucker are the order of the day. One of the most famous makers of the style is Orlebar Brown, which offers a luxe version that is well worth the investment if it fits your style. If you’d like to spend a little less, investigate brands like Spier & Mackay, Sunspel, Bonobos, Buck Mason, and Dandy Del Mar; they all consistently offer tailored trunks that won’t break the bank.

Wear it with: Slim-cut shirts—try something in linen or, if you’re feeling extra bold, crochet. Big sunglasses that suggest you might be an incognito celebrity. Leather sandals or espadrilles.

Spier & Mackay Side Tab Swim Shorts

Credit: Spier & Mackay

Sunspel Tailored Swim Shorts

Orlebar Brown Bulldog Seersucker Swim Shorts

The Board Short

Jean Baptiste Lacroix//Getty Images

Matthew McConaughey wearing boards is al… well, you know the rest.

If you surf, you already know about one of the biggest advantages of the board short: security. Instead of an elastic waistband or a single snap, it’s secured with a cord that’s been passed through a set of grommeted holes and tied off. (Kind of like how you tie your shoes.) If a wave hits, there’s very little chance your bottoms are going to slide off and reveal, well … your bottom. Board shorts also tend to be longer than trunks, offering more coverage to protect from friction (from the top of a board) and UV rays.

From a style perspective, board shorts were something of a punchline for a while, as they hung comically low, loose, and long in the 2000s. Nowadays, though, brands like Outerknown (the brainchild of revered surfer Kelly Slater) have revived the style’s credibility with improved fits and updated tech like welded seams. A couple brands that were already mentioned—Buck Mason and Bather, for instance—do great takes. You can also find dependable board shorts from Birdwell, a stalwart on the scene, as well as Sundek, Florence, O’Neill, Katin, and Pilgrim Surf Supply. Prints aren’t as popular as they are with trunks, but bright colors (think fire-engine red) and stripes really fit with the board-short vibe.

Wear it with: Graphic tees and rash guards. Sporty sunglasses (maybe even wraparounds) that, whether ironically or not, reference the ’90s. Slip-on shoes, preferably of the checkerboard variety. Flip-flops, if you must.

Birdwell 300 Comp Stripe Board Shorts

Credit: Birdwell

Outerknown Apex Evolution Trunk By Kelly Slater

Buck Mason Japanese Oxford Board Short

Credit: Buck Mason

Okay, but What About…

Nancy Moran//Getty Images

Harrison Ford playing football (?) in a Speedo-type swimsuit (!) in 1981.

A Speedo? Well, technically that’s a brand name, but it’s pulled a “Band-Aid” (or a “Velcro”) and become shorthand for a whole category. In this particular case, that item is a low-slung brief that leaves very little to the imagination. It’s a look, for sure. And you may be able to carry it off, especially if you’re in a foreign country. But as a general rule? Avoid.

When to Wear Your Swimsuit

The simple answer here is crushingly self-evident. You should wear your swimsuit when you’re swimming. Or soaking. Or floating. Anytime you’re in the water, basically. But there are further considerations to keep in mind. What if, for instance, you’re going to be beach- or poolside and don’t plan on going in the water? You could wear something like shorts or breezy trousers. But a swimsuit is still your best bet. It looks right at home, for one thing. There’s also the off chance you’ll decide you do want to take a dip. Dress optimistically. It’s better to be prepared than to find yourself sitting in soggy shorts for the next few hours.

Archive Photos//Getty Images

Sean Connery and Claudine Auger in Thunderball, 1965.

Can I Wear My Swimsuit…

…to the Gym?

In a pinch. But it’s a little weird if it looks too swimsuit-y.

Notable exception: If the gym has a pool. In which case … c’mon. Why are you even asking?

…on a Hike?

Great idea! Provided it’s the right kind of swimsuit. A classic trunk—quick-drying material, supportive liner—is great for a hike, especially in the summer heat.

Notable exception: If the hike is serious—like overnight with camping equipment—you should not be taking notes on your gear from a story about swimsuits.

…to the Bar?

Is it a beach bar? Go for it. A swim-up bar? The suit is downright required. Any other bar? Proceed with caution.

Notable exception: If you’re wearing tailored trunks, you can get away with them in any environment in which shorts are acceptable.

…out to Brunch?

Maybe. They should look like shorts instead of obvious swim trunks, though. Even then, wouldn’t it be easier to just wear, you know, actual shorts?

Notable exception: It’s laundry day.