Flip-Flops Are Trying to Be Cool Again. Should We Let Them?

The flip-flop is making a break for relevance—with leather finishes, designer co-signs, and a whole lot of exposed toes. Here’s how women can wear them now.

By Sean Castelo III July 07, 2025

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Usually reserved for beachside showers and bodega runs, the flip-flop has crept back into fashion’s good graces—thong-first. Thanks to the likes of Louis Vuitton, Prada, Giorgio Armani, and Auralee, leather finishes and color-blocked straps now attempt to elevate what was once the ultimate afterthought. Even Havaianas is flexing, going furry in a Dolce & Gabbana collab that feels both ridiculous and right on time.

Jonathan Bailey set the internet aflame when he arrived at the Jurassic World: Rebirth premiere in The Row’s high-end take on the style. And because it’s Bailey—smoldering, stylish, unbothered—it landed. But can the average guy channel that same nonchalance? Or will he just look like he forgot to finish getting dressed?

Open-toed shoes have had a longer runway in women’s wear—dresses, socks, business settings, the works. But let’s be honest: bare toes are still a gamble, especially in work environments.

For men, toes are still taboo. Especially when your surroundings are more sidewalk slush than Santorini. But in an age where early 2000s style is enjoying a renaissance, maybe it’s not so strange that the flip-flop is flipping the script.

How Women Can Wear Flip-Flops Without Looking Like They Gave Up

Choose Flip-Flops with a Point of View

Rubber basics? Leave those for the pedicure chair. Go for elevated materials—leather, satin, metallics—or unexpected textures. A sculptural sole or unexpected color turns a poolside staple into a purposeful style move.

Dress Up the Contrast

If your footwear nods to the beach, make sure the rest of you show effort. Pair flip-flops with tailored trousers, an oversized blazer, or a crisp button-down. The trick is in tension: relaxed below, refined above.

Treat Toes Like a Detail

If you’re showing them, polish them. A clean pedicure, sheer socks, or even toe rings (if you’re feeling early-2000s brave) turn bare feet into a styling choice—not a climate excuse.

Whether it’s haute or hopeless depends on the confidence, and the pedicure. As with all fashion risks, you can’t blame a slipper for trying.

Photos: LOUIS VUITTON, PRADA, GIORGIO ARMANI, DRIES VAN NOTEN, and AURALEE