7 ways to wear heeled flip-flops this season, according to the street-style set

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July 19, 2025

On July 19, 2025

Heeled flip-flops are back—with The Row championing their sleek, stripped-down reinvention. Elevated and unfussy, they’re proof that even the simplest silhouettes can feel fresh again.

The spring/summer 2025 collections were full of flip-flop hybrids, as seen at Alaïa, Miu Miu and Dior, which are more elevated than your usual pool or shower shoe. Miuccia Prada, always one to push boundaries, presented a thong court pump at Miu Miu as her answer to the ugly shoe of 2025, while the likes of Toteme have leaned into a sleeker, more minimalist aesthetic that is very aligned with Jennifer Aniston’s low-key ’90s aesthetic.

When it comes to styling, the opportunities are so much broader than with a rubber Havaiana, which work in very few contexts outside of the beach. In fact, there aren’t many occasions where you can’t make a heeled flip-flop work – Vogue editors have been wearing heeled thong sandals to formal dinners, important work events and summer weddings, while they will also pair well with more casual pieces in your weekend rotation.

The street-style crowd have been taking a very Carrie Bradshaw approach to the shoe, pairing thong kitten heels with Adam Sandler-style track shorts, jorts and sports jerseys. The low heel and simple straps makes them more relaxed than your typical high heel, but the added lift provides a dollop of extra polish, making them a “so wrong it’s right”, off-kilter addition to sportswear. It can also pay to lean into a retro aesthetic and style them with other late ’90s/ early Noughties comebacks, such as knee-length capri pants and baggy cargo pants.

The only circumstance where you might want to avoid these is at the home of the original flip-flop: the beach (sinking into sand is never a good look). Having said that, Hailey Bieber – a fan of the heeled thong – recently wore a pair to a poolside Rhode event in Mallorca, leaning into OTT Euro style in a head-to-toe lemon Pucci Iride print. It’s not often that you find a shoe that looks just as good with a floor-sweeping evening gown as a string bikini.

To see just how versatile this summer’s trending shoe is, keep scrolling for seven ways the street-style set have been styling the chic heeled flip-flops.