With spring in full effect and summer just around the corner, knowing what shoes to wear on a daily basis is just as tricky as knowing whether or not to take a jacket. Too warm for boots, too cold for a barely-there sandal, a season of “will it, won’t it” weather is impossible to plan for, but after checking the forecasts (and remaining optimistic), we’ve finally taken our warm weather shoes out of retirement. And so, it would seem, have celebs, enter: Hailey Bieber and Kendall Jenner.
(Image credit: Backgrid/Splash)
It’s not often we can rely on American celebs to dictate what to wear seasonally as they have the benefit of far better weather, but both Hailey and Kendall’s evening looks last night were all about the humble spring/summer sandal that we hadn’t considered partywear—the flip flop. Yes, heeled thong sandals are officially dressy enough (and cool enough) to be worn after dark, so even if you can’t quite imagine adding a sandal to your daytime looks quite yet, heeled flip flops are a chic option for after dark.
Pairing hers with a simple silk LBD, Hailey’s look was the dressed up answer to Kendall’s Adidas track jacket and black shorts, conclusive proof that not only are these sandals comfy enough to wear all night, they’re also versatile enough to style up and down. Curious to see how else you can wear the look? Keep scrolling to see how influencers are adopting the shoe trend too.
How to Wear the Heeled Flip Flop Trend in 2026
(Image credit: @ingridedvinsen)
Style Notes: Ingrid’s slightly sheer top and lace skirt make the perfect day-to-night outfit when paired with dressier heeled flip flops for a little extra lift.
(Image credit: @johannapiispa)
Style Notes: Johanna manages to tick off several trends at once by styling a collarless blazer with trending capri trousers, a ’90s headband and a thong sandal.
(Image credit: @johannapiispa)
Style Notes: She also has a pair of white toe post sandals in her wardrobe for adding a point of interest to monochrome tailored looks like this blazer and balloon trouser combination.
Still need convincing? Keep scrolling to see the best thong sandals you can shop now. They’re all your outfit needs to go from winter blues to summer mood with just the switch of a shoe.
Shop the Best Heeled Flip Flops 2026
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