The Ultra-Specific Shorts and Shoe Combination the Chicest People Are Wearing Right Now

In the summer months, I like to keep my daily styling as uncomplicated as possible. That means leaning on simple outfit formulas I can pull together in minutes—no overthinking required. While I often default to classics like jeans and a T-shirt or a breezy dress with Mary Janes, there’s one combination I’ve been coming back to a lot this season, one that feels especially fresh for 2025: Bermuda shorts and heeled flip flops.

Just as easy to throw together as my usual go-tos, this combination feels that little bit more elevated—refined enough to transition from casual afternoons into smarter settings.

Bermuda shorts, which graze the knee or fall just below, offer a polished alternative to the thigh-skimming styles we’ve worn for years. Imparting sophistication, I think their tailored finish makes them more akin to pencil skirts than to cut-off shorts—lending them the same polished enegry that structured skirts retain.

Meanwhile, a heeled flip-flop adds a playful component. With their slender straps and subtle heel, they toe the line between smart and casual, lending an unfussy charm that balances the formality of the tailored shorts.

This week, I spotted Hailey Bieber step out in this pairing, as if to prove my point. Styling a cropped black tee, Bermuda shorts, baseball cap, and—crucially—kitten-heeled flip flops, Bieber’s outfit felt effortless yet considered. Where trainers would have made the outfit veer too casual and ballet flats could have been too covered up, her flip-flop heels brought just enough interest to elevate the whole look without overwhelming it.

It’s not just Hailey, either—several of my favourite fashion people have worn long shorts and heeled flip flops in the past couple of weeks, too. Needless to say, I’m inspired to do the same and see myself relying on the look all season long.