I Went From Flip-Flop Hater to Convert. Here’s My Summer Rotation.

By,a writer and market editor in Cincinnati.His work has appeared in Huckberry, Sprezza, and Valet. He writes about menswear and fashion.
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Photo-Illustration: The Strategist; Photos: Leon Hedgepeth

I was a longtime hater of flip-flops. Maybe it was insecurity about showing my feet to the world or some misplaced notion that guys shouldn’t wear them. Either way that all started to change about five years ago when I became a little more comfortable showing some skin, starting with my heels. Like many other menswear nerds at the time, I hopped on theBirkenstock Bostonbandwagon. Exposing my heels made me realize,Hey, this isn’t so bad after all.

Beyond my reluctance to let the dogs out, flip-flops also never seemed to fit me right. I’m usually a size 10 insneakers, but my feet are narrow enough that forloafers, boots, boat shoes, and flip-flops, I typically wear a size 8. In that size, they fit as they should (snug) and don’t flop around on my feet. That completely changed my perspective.

Last year, after learning how to properly care for my feet, I finally committed to a pair of flip-flops. With record-breaking temperatures continuing this summer, and even my favorite canvas sneakers feeling too hot, flip-flops have become the most practical footwear option in my rotation. Below are my current favorites, from leather pairs to rugged Vibram-soled options to featherlight cushioned styles that can float.

Photo: Leon Hedgepeth

My favorite pairs

Bombas Men's Sunrise Leather Flip Flop
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Bedrock Rockhound Leather Sandal
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UGG Men's Seaside II Flip
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Alltheflip-flopsI’vebeenwearingthissummer

The most lightweight

Teva Men’s Mush II Flip-Flop
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TheseTevasgot me hooked on open-toed shoes. I’ve worn them to our local garden nursery, backyard barbecues, and the pool. When I first slipped them on, they had a spongy feel and my feet immediately sank into the brand’s Mush top sole, for which the flip-flops are named and that gradually molds to the shape of your feet. I haven’t had any issues with chafing between my toes, and the EVA outsole keeps them comfortable for walks back from the pool. These flip-flops are ideal for casual wear and water activities, but the foam outsole is too slippery for hiking or more rugged terrain.

Photo: Leon Hedgepeth

My most-worn pair

Bombas Men’s Sunrise Leather Flip Flop
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Bombas’s taupe nubuck leather pair has easily been the flip-flop I’ve logged the most hours in this summer. The first time I wore them, my mom asked, “Are those Rainbow sandals?” My editor also mentioned that they looked similar to Rainbows, too. They’re undeniably similar — but my only experience with Rainbows was seeing my middle-school classmates in North Carolina wearing them with polos and khaki shorts, which wasthesummer uniform at the time.

So I slipped into the Bombas without any preconceived notions, and I can’t emphasize enough how comfortable they are. Because they’re made of nubuck leather I keep them away from the water, but I wear them everywhere else, from grocery-store runs to patio dinners. Besides shorts, I also wear them with dark-brown chinos or faded blue jeans that hit right at the ankle for a somewhat less casual look. The leather strap keeps my foot secure without feeling restrictive, and one of my favorite things about the sandals is watching the leather develop a patina. They’ve molded to my feet over time, the sun has given them even more character, and the rubber outsole stays comfortable even after hours of walking.

Photo: Leon Hedgepeth

The best at protecting your toes

Keen Men’s Waimea Leather Flip-Flop
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Keen’s flip-flops took the most getting used to because they partially cover my first two toes while leaving the other three exposed. After wearing these to take my son to the park, I finally understood the logic behind the toe bumper. I walked across everything from mulch and grass to sand, and even survived a few water-fountain mishaps, yet my toes stayed protected and dry without a single stub.

I’m planning to pack these for my trip to Maryland next month to visit family, where I expect to wear them in the shallow waters at Rocky Gap for extra protection against rocks and shells. The outsole also helps keep my feet in place, even when the sandals get a little damp.

Photo: Leon Hedgepeth

The most cushioned

UGG Men’s Seaside II Flip
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I’ve worn these UGG flip-flops several times to eat at Northstar Café, which I’d describe as the Ohio equivalent of the Houston’s restaurant group. And on those occasions, I always wear them with pants.

The full-grain leather is supple, and my feet sink into them the way the rest of my body sinks into my leather lounge chair. The straps are thicker and wider than those of the other flip-flops I’ve tried, giving them extra support and helping them stay on my feet. My favorite design detail is the stitching, which resembles the beefroll stitching found on loafers, where thick rolls of leather along the upper are stitched into place. It’s a subtle touch that gives the flip-flops a more refined look while also making them more durable.

Photo: Leon Hedgepeth

The best for water and trails

Chaco Men’s Rapid Pro Flip
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These Chacos are pretty bare bones but have a workwear-inspired look that I like. They’re made from a durable PU construction with webbing that dries quickly, though it does take a few wears to break in the straps. The footbed runs narrow, which works well for me since I have a higher arch, and the Vibram outsole provides excellent traction across a variety of terrain. I will say these are the heaviest flip-flops in my rotation, but they’re also among the most adaptable. I wore them on a trip to the water park with my son, and they dried within 15 to 20 minutes while remaining comfortable enough to walk around in.

Photo: Leon Hedgepeth

The best fitting

Bedrock Rockhound Leather Sandal
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I’ve had my eyes on Bedrock Sandals for a while. The Rockhound is the brand’s first-ever flip-flop since launching 15 years ago. While I’m not looking to hike in flip-flops, I do appreciate a sturdy pair that can last a lifetime. I’ve only had these for about a week, and I can already feel the nubuck leather molding to my feet with each wear. They’re already the best-fitting flip-flops I own, thanks to the adjustable G-hook strap system, which lets you fine-tune the fit in a way I haven’t seen on any other pair.

I don’t plan on wearing these near open water since the leather can get slippery when wet, though they’re still more water-friendly than most leather sandals thanks to the brand’s construction. The 3-D footbed provides much-needed arch support, and the Vibram outsole offers excellent traction, much like Chaco’s. Unlike the Chacos, though, these don’t feel nearly as heavy, likely because they feature a leather upper instead of a synthetic one. I won’t be putting these through mountain trails, but I do plan on wearing them every day until it’s time to break out socks again. The price is admittedly steep for a pair of flip-flops, but they’re built to last. Bedrock offers a resole and repair program, making these the kind of sandals you can keep for years.

Photo: Leon Hedgepeth

More men’s summer shoes we like

Camper Don Fisherman Sandals
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$133
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A good option for a summer beach-and-city trip with lots of walking.

SeaVees Men’s Tiburon Trekker
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$132
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Leather mules that fit a high instep.

Aurora Middle English Men's Shoes
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Montbell Sock-on Sandals
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$50

Sock-friendly sandals senior writer Michael Zhao discovered in the French countryside.

Birkenstock Arizona Essentials EVA
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Chaco Men's Z1 Classic Outdoor Sandal
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$71
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A great-fitting pair of water-friendly hiking sandals.

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