The Do’s and Don’ts of Wearing Sandals This Summer

Naked toes. In public. The very thought of it makes some guys shudder. Others have a more laissez-faire attitude toward the issue. And others still are full-blown enthusiasts, ready and raring to let their dogs out as soon as the weather gets warm. Is it any wonder that the sandals question—how to wear them, where to wear them, whether to wear them at all—is one of the most hotly debated topics in the world of menswear?

We’re not here to fight with the anti-sandal crowd. As we said previously on the topic of shorts, it’s too damn hot to abide by some self-imposed restriction and suffer because of it. If you prefer shoes, go forth and be happy. But if you’re in the mood to let your little piggies see the sunlight this summer, you’ve come to the right place.

It remains, after all, “a great time to be a toe,” as the The New York Times noted last summer. In all of fashion, but notably in menswear, there’s something of a sandal resurgence happening. From the catwalks of Milan and Paris to the streets of New York—and, if it hasn’t happened already, the streets of your neighborhood too—open-toed shoes are having one hell of a moment.

Which, of course, comes with its own set of issues. If you’ve previously been a non-sandal sort of guy, you might be wondering where to begin. What style should you opt for? What should you wear with it—and where? And what if you only want to dip your, ahem, toe into the deep pool of sandal opportunities?

We’ve got the answers to all of those questions and more below. But let’s start with a look at the three main players.

Jason Momoa makes the case for flip-flops.

Ah, the humble flip-flop. (Some call it a “thong,” which confuses Americans to no end.) This is, to many, the quintessential sandal. It’s got a couple of straps that meet at the space between your big toe and second toe, a sole underneath, and pretty much nothing else. It’s simple. It’s functional. It’s easy. At least it should be.

The thing about flip-flops is that so many of them are of the variety that you buy at drugstores or beachside shops that overcharge underprepared tourists. You know the flip-flops we’re talking about. They cut up your feet and give you blisters—or they try to, if they can get the job done before the straps pop out of the sole or they’re otherwise rendered unwearable. These flip-flops categorically suck.

But there are also good flip-flops. Flip-flops that are built for longevity and comfort and all the things that you should expect from your footwear. Reef does a great job. As do Havaianas, Rainbow, Oofos, OluKai, and Teva. Flip-flops from any of these brands do not suck. The thing is, they’re still flip-flops, which means that from a style perspective they’re … tricky. You already know that you can wear them on the beach and the boardwalk. As for everywhere else? That’s tougher. The office is a no-go. The bar too—unless it’s a beach bar. And unless you like stomped toes and broken nails, they should be avoided on all public transit and in most of the city in general.

But the aperture of flip-flop acceptability is widening. Consider this: Prada showed a bunch of flip-flops as part of the fashion house’s spring 2026 runway show. Brunello Cucinelli makes a mean pair. As does Gucci. High fashion, it seems, has embraced the flip-flop. You may want to consider it too.

Wear them with: Board shorts and camp-collar shirts, of course. Plus battered tees and equally well-worn chinos. You could even try a pair with a linen suit, if you’re feeling adventurous (but you better be feeling pretty adventurous).

Jeremy Allen White takes his slides for a stroll.

They’re not just for the shower. Remember when Jeremy Allen White took his Adidas slides out for a stroll a couple summers back? We sure do. All due credit to the man otherwise known as Carmy, because he showed the whole world how cool and relaxed you can look when you walk around the block wearing a pared-down look—in his case, a white tee and worn-out jeans—and a pair of slides. It makes sense. Slides are made for comfort and ease. Hell, even the name is an indicator of how user-friendly they are. You just slide them on. That’s why they’re the go-to pick for guys recovering from a workout, lounging around the house, or, yeah, shuffling from their dorm room to the communal shower.

The most classic of slides feature a single strap over the instep of your foot. It’s sporty. Simple. You can’t go wrong with versions from Adidas (but of course), Nike, Oofos, and basically every other brand with its roots in the athletic world. But that’s not the only slide style out there. One of our favorites, if you’re looking to get a little fancy, is a crossover, two-strap design, often executed in leather. It’s like if your favorite post-exercise sandals decided to take a trip to the Riviera instead of languishing in your gym bag. Todd Snyder makes a great pair, as do Bruno Magli, Zegna, and Christian Louboutin. In fact, you can find upscale slides from most of the major fashion houses, though their offerings are going to change from season to season. And if you lean a little more crunchy, remember that Birkenstock’s iconic Arizona sandal is technically a slide.

Wear them with: A warmup suit, if you’re taking the “sporty” thing really seriously. A pair of beat-up jeans and a white tee, à la Jeremy Allen White. Linen trousers and a billowy shirt—also linen, naturally—if you want to get fancy. A tropical wool suit if you want to get even fancier.

Director Yorgos Lanthimos dressed his fisherman sandals up for the Kinds of Kindness photo call with Willem Dafoe and Emma Stone.

You may or may not be familiar with the name “fisherman sandals”—one Esquire staffer prefers to refer to them as Gladiator 2 sandals—but we’re sure you’ve seen them before. They’re more structured and substantial than the others on this list, with leather straps forming a sort of cage around the foot. There are a couple advantages to this style of sandals, the first and most obvious of which being that they’re the ones that come closest to the look and feel of shoes while still letting that sweet summer breeze caress your feet. They’re a little less out-there when it comes to putting your toes, well … out there. If you’re shy or squeamish, they can be a great way to slowly transition to full-on sandal fandom (or not, up to you). The second is that they offer just a touch more stomp protection than flip-flops and slides, so you can wear them on the subway if you’re feeling bold.

Take a look around the Internet and you’ll see that there are endless iterations on details. The number of straps, whether there’s some kind of toe cap, a closed versus an open heel—all these things are matters of preference (though in general we feel that the fully open-toed takes on the fisherman sandal look kind of wrong). As for which brands do it right? Well, a lot of them. Dr. Martens, Sabah, Grenson (which makes the sandals in the photo at the top of this story), and Ancient Greek Sandals all do very nice takes on the design, as do Church’s, Scaroso, and Vinny’s. Fashion-oriented brands like Todd Snyder and Prada also have great riffs on fisherman sandals. Just pick your price point, look for a name you know, and you’re unlikely to go wrong.

Wear them with: High-waisted trousers and a simple white tank top. Patch-pocket shorts and a boxy button-up. A cream colored linen-and-silk suit to your friend’s summer wedding. Of all the sandals on this list, these are the easiest to play around with, so have fun.

Pro tip: If fisherman sandals aren’t quite right for you, huaraches do a very similar thing but with a slightly different vibe. They’re available from a ton of makers, but Chamula is one of Esquire’s favorites.

Dior and Birkenstock’s take on the clog.

Clogs aren’t sandals, if you ask us. With a fully closed toe, they’re excluded from genus Sandal. That said, many minds tend to jump to clogs when the sandal conversation comes up, so we’re going to touch on them. The closest to true sandals are probably—brace yourselves—Crocs. The perforations in the brand’s classic clogs offer airflow nearing sandal levels, and with the strap flipped forward your heels are entirely uncovered. They’re also waterproof—so great for wearing to the beach, the pool, or the Slip ’n Slide in a pinch. Next in this taxonomy are open-backed styles like the Birkenstock Boston, possibly the best clog of all time. There are tons of dupes out there, but nothing hits quite like the Boston. After that come clogs with a dedicated backstrap, which occupy a kind of liminal space. The collab between Birkenstock and Dior, shown above, is difficult to classify but extremely cool regardless. And finally you’ve got clogs with a fully closed heel—in other words, shoes. You may have noticed cool guys with a gardening-adjacent vibe wearing plastic ones called the Gardana from a French brand aptly named Plasticana. Unfortunately, those are still so popular that they’re not so easy to find in stock. But if you search around—try Gardenheir for the “Vert” color and Feature Flora for the buzzy “Sepia”—you might be able to find a pair in your size. Again, they’re not sandals. But they’re all great summer footwear options.

Sometimes. Use your judgment. Never with flip-flops and never in black, unless you want to look like a German tourist from the ’90s.

Socks with sandals! It’s up to you!

As with so many summer staples, the guiding principle for wearing sandals is the more formal the environment, the less acceptable they are. You simply don’t wear sandals with black tie, not that you needed to hear that. The beach, on the other hand, is about as casual as you get; any and all sandals will look right at home where the sand meets the sea. To put it another way: Brunch is, on the whole, a chiller experience than dinner. Sandals stand a much better chance of looking good when you’re ordering eggs Benedict and a Bloody Mary than they would when steak and martinis are on the menu.

Of course, this guiding principle is just guidance. (It’s right there in the name!) When it comes to specific situations, you need to start thinking about context—and the sandals themselves. Fisherman sandals, for instance, are better suited to dressing up than flip-flops. You’ll have an easier time getting away with wearing them to the office with a pair of smart trousers and a nice shirt on a sweltering day than you would if your toes were on full display. (Slides, for reference, fall somewhere in the middle of the dress-up-ability spectrum.)

Perhaps the best way to tackle the problem in real time is to simply ask yourself the question Am I comfortable with everyone at [insert event here] seeing my naked toes? If there’s even a moment of hesitation, it’s time to reach for a pair of proper lace-ups or loafers. If not? Let those piggies go to market.