I know what you’re thinking. How on Earth can you complicate wearing a swimsuit? You put it on; you go in the water. Done deal. I get where you’re coming from. If all you want to do when it gets hot is grab whatever you have lying around and start splashing, you are absolutely free to do so. It’s summer, which is not the time to worry unnecessarily. It’s the time to take it easy and enjoy yourself by the pool, at the beach—hell, even running through a sprinkler.
Ah, but there’s the rub. Because this is the season when swimwear becomes not just an occasional necessity but a staple of your off-duty wardrobe. And as is true with so many things in the world of menswear, a greater understanding of the nuances of what you’re wearing can make for a far more enjoyable—not to mention more stylish—experience.
So, we’re going to get into those nuances. We’ll get our feet wet (sorry) with the core types of swimsuits on the market. We’ll dip our toes (sorry again) into how to style them. We’ll even go against the current (ugh) and explore a few instances in which wearing a swimsuit for something other than swimming is an entirely acceptable idea. Ready? Let’s dive in (ha!).
The Classic Swim Trunk
Of course Don Draper was a classic swim trunk guy.
This is what most folks imagine when they think about men’s swimwear. 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, and 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-expensize fashion brands like Buck Mason and Todd Snyder. And if you want to get fancy, you could always opt for St. Tropez-inspired Vilebrequin, 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 Shorts 5″
Todd Snyder 5″ Montauk Swim Trunk
Vilebrequin x Highsnobiety Swim Trunks
The Tailored Swim Trunk
Tailored trunks have been a good call since the days of Connery’s 007.
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—or any other gym day—during the winter and spring. As with the classic trunk, you’re usually getting a couple of 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 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. Strappy leather sandals or espadrilles.
Bonobos Tropez Swim Short
Sunspel Tailored Swim Shorts
Now 31% Off
Orlebar Brown Bulldog Swim Shorts
The Board Short
Naturally, the Baywatch guys wear board shorts.
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) or 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 rashguards. 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.
Outerknown All Time Scallop Trunks
Buck Mason Japanese Oxford Board Short
OK, but What About…
Approach with caution.
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.
Daniel Craig’s Bond set off a stir with the swimsuit in this Casino Royale scene.
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.
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