If you’ve been keeping track of the trend cycle recently, you will have noticed that one shoe style is particularly prominent: heeled flip-flops. Blame it on fashion’s current fixation with hybrid footwear, but endless designers and celebrities are pushing the agenda for this elevated and minimalist sandal to reach unprecedented heights. (Pardon the pun.)
Naturally, with countless sightings of this style comes the inevitable question of how exactly to style it. Thankfully, the endless appearances naturally mean there are plenty of heeled flip-flop outfits to derive inspiration from.
Leading the charge is none other than Hailey Bieber, who has made this shoe a crucial part of her off-duty wardrobe. The model-turned-mogul has paired the shoe with everything, from a knee-length skirt and cropped jumper when promoting the launch of Rhode Beauty’s new bronzers and tinted glazing milks in Rhode Island to polka-dot capris when running errands through New York City. On the West Coast, Kaia Gerber recently styled heeled flip-flops with a bodycon dress and funnel-neck trench coat for an outing at Santa Monica hot spot Giorgio Baldi.
Of course, those in the know will be aware that heeled flip-flops have been a staple in well-edited wardrobes since the ‘90s. It’s this exact vein of decisive minimalism à la Carolyn Bessette Kennedy that brands like Toteme, The Row and Manolo Blahnik perfectly achieve. But as this summer prioritises the more lurid and maximalist palette of the Y2K aesthetic, it’s Jimmy Choo’s jelly sandals and Ancient Greek Sandals’s Summer Roberts-inspired wedges that really dominate conversations.
And therein lies the appeal of heeled flip-flops. With a simplistic and rudimentary shape, the shoe itself can be adopted and recontextualised in so many different ways to suit so many different styles. Sleek, sophisticated and incredibly versatile, keep scrolling through to uncover the chicest ways tastemakers and style savants are wearing heeled flip-flop outfits this summer.
5 Chic Heeled Flip-Flop Outfits to Wear in Summer 2026
1. Little Black Dress + Minimal Jewellery + Heeled Flip-Flops
Style Notes: With a shoe as understated and refined as this, why not embrace the same characteristics with a little black dress and minimal jewellery? This silhouette has been a go-to for sophisticated dressers since Gabrielle Chanel entered it into the sartorial lexicon over a century ago. But with riveting options, including the sheer style from Réalisation Par seen here, the classic hue and polished silhouette always feel contemporary.
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