You Can Still Wear Flip-Flops and Look Cool in 2026, But Only If You Wear Them Exactly Like This

And it feels very CBK-approved.

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Sarah Pidgeon
Sarah Pidgeon in an all-black outfit with flip flops.
(Image credit: Backgrid)
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Everyone said flip flops would be over by this summer but they all couldn't have been more wrong. If anything, the controversial sandal is more popular than ever. Even in New York, where having your toes out can be considered sacrilege, cool girls are wearing them on repeat. Can you blame them? There isn't any other flat that feels as casual and cool.

Sarah Pidgeon, though, recently demonstrated that the shoe doesn't always have to feel nonchalant. She actually proved it can feel quite fancy with the right styling, which feels very apt considering her recent portrayal of Carolyn Bessette Kennedy on Love Story.

Sarah Pidgeon's Outfit

Sarah Pidgeon all-black outfit with heeled flip flops

On Sarah Pidgeon: Toteme Black Cropped Satin Camisole ($620), Toteme Layered Satin Midi Skirt ($720), Alaia Le Teckel Bag ($3,050), and The Row Sacha Heel Thong Sandal ($1,000)

(Image credit: Backgrid)

Her flop of choice was of the heeled variety, the Row Sacha heel thong sandal to be exact. And she paired them with a matching Toteme set and an Alaia Le Teckel bag. The all-black look was elevated and simple but most importantly, it was a reminder that wearing flip flops doesn't always have to feel like a relaxed vacation. Long live the flip flop!

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Tara Gonzalez
Tara Gonzalez
Senior Fashion & Social Editor

Tara Gonzalez is a senior fashion and social editor at WhoWhatWear. where she is interested in exploring the intersection of fashion and culture and why we are drawn to wearing the things we wear and what that says about the world we live in. Previously she worked as a senior fashion editor at Harper's Bazaar. When she isn't writing trend deep dives for WWW, she's working on her newsletter on Substack, Cult Classic, which explores the very best fashion in film and television. She has a degree in creative writing from The University of Pennsylvania. She lives in Brooklyn with her boyfriend and pug Bjork, the later of which has a very extensive collection of dog-sized Sandy Liang sweaters.