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.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 Chic Nordstrom Outfits I Put Together for Her Under $425Outdated prints and "ugly" shoes included.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.
-
Click Here for Proof That This Sophisticated Shoe Color Works With Both Jeans and DressesVersatile and chic.
-
How I Let My Many Personalities Flourish This Fashion MonthHere's everything I wore, from New York to Paris.
-
I'm Seeing This Quietly Chic Flat-Shoe Style Paired With Outfits Everywhere This FallThere are endless ways to wear it.
-
If You're Tired of Predictable Fall Outfits, Try This Styling Trick InsteadBold and anything but basic.
-
I Live in NYC—These Are the 5 Essential Pieces I Rely On Every FallMy favorite.
-
It's Here: The Elegant Shoe Trend Fashion People Are Trading Kitten Heels ForElizabeth Olsen is keyed in, per usual.
