Heeled Flip-Flops Are Summer's Chicest Shoe Trend—Here's How to Wear Them
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.
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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.
Shop the Look:
Reformation
Joni Knit Dress
Made from a soft, jersey fabric and finished with quaint scalloped trims, this dress is both delicate and daring.
Organic shapes are one of the biggest jewellery trends of 2026.
Toteme
Leather Heeled Flip Flops Black
If you were to ask any woman with taste where their heeled flip-flops were from, they'll most likely tell you Toteme.
2. White Scoop-Neck Top + Khaki Jeans + Heeled Flip-Flop Wedges
Style Notes: Elevate your everyday uniform with this polished shoe choice. Heeled flip-flops are both inherently elegant and effortless, courtesy of the fact that they straddle the simplicity of a flat sandal with the refinement and glamour of a heel. Pairing them with trend-forward basics like a scoop-neck white top and khaki jeans will ensure that you feel put together for any event you have on your calendar that day. (And the spontaneous ones, too.)
