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. Whilst 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 cut-off shorts, lending them the same polished energy of structured skirts. Meanwhile, a heeled flip-flop adds a playful component. With their slender straps and subtle heel, they toe the line (no pun intended) 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-heel 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 Bieber, 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.
Keep scrolling for the Bermuda shorts and heeled flip-flops I’m eyeing right now.
SHOP BERMUDA SHORTS AND HEELED FLIP-FLOPS:
Shop these whilst they're on sale.
These look so much more expensive than they actually are.
This chocolate-brown shade is so easy to slot into a capsule wardrobe.
These also come in black and chocolate brown.
Style this with the matching vest or wear with a simple tee.
Style these with Bermuda shorts or pair with a floaty dress.
The linen composition ensures a breezy finish that will keep you comfortable during the height of summer.
These also come in five other shades.
Style these with heeled flip-flops or pair with pretty Mary Janes.
Sleek, comfortable and perfect summer styling, the heeled flip-flop trend is only just getting started.
These elegant shorts will style just as well with a neat button-down as any pair of tailored trousers.
The satin composition lends these an elevated edge.
-
I'm a Fashion Editor Who Hates Flats—6 Heeled Shoe Trends I'm Wearing This Winter (and 6 I'm Skipping)Heels just make me feel so confident.
-
I Just Created 8 Spectacular Fall Outfits From Nordstrom for Under $500Major inspo ahead.
-
If the Choice Is Between Black Pumps and This Trendier Color, It Girls Know the Latter Looks CoolerIncluding It-girl Elizabeth Olsen.
-
If You Want to Look Chic and Rich This Winter, Make Sure You Own This Non-Denim Pant TrendSee what we’re talking about inside.
-
Every Fashion Person Has a Version of These 6 Night-Out LooksHow to reply to "What are you wearing out tonight?"
-
The 2025 Way to Wear Sneakers This WinterOutfit inspiration inside.
-
5 Non-Dated Ways People in Paris, NYC, and L.A. Are Styling Leather Pants Right NowNow all I want to wear are leather pants.
-
Sorry, Crewneck Tees—in 2026, Everyone With Taste Will Be Layering Sweaters Like ThisThe recipe for a perfect winter outfit.
