The style set have swapped sandals for flip flops
I have a confession. After a decade-long love affair, I have officially retired my Birkenstocks and replaced them with comfy flip flops: the simplest, flimsiest and once most deeply uncool shoe imaginable. “Comfy” being the operative word here: not all flip flops are made equal – and I'm only interested in pairs that I can walk 10k steps in.
iQUSHION Ergonomic Flip-Flops
Arch Support Flip Flops
H&M Contrast Flip-flops
Don’t get me wrong, I remain emotionally indebted to those cork-bottomed sliders. They carried me through 20,000-step days while backpacking around South East Asia at circa 2018, survived countless British festivals and long summers inter-railing in Europe. But somewhere between my frontal lobe fully developing and a trip to Copenhagen Fashion Week in 2025, I realised I'd been influenced. The flip flop was no longer simply the shoe you shoved into your suitcase for the hotel pool. It had become the ultimate cool-girl sandal.
In Copenhagen, I watched the style set pair classic rubber flip-flops with the kind of outfits I would once have deemed far too polished for them: oversized tailoring, sheer skirts, longline dresses and crisp cotton separates. The contrast was the entire point. The humble flip-flop made even the most put-together outfit feel relaxed, modern and infinitely more chic.
READ MORE: 6 summer sandal trends the cool girls of London are wearing in 2026.

Moritz Scholz/Getty Images

Raimonda Kulikauskiene/Getty Images
Naturally, flip flops are now being worn with everything from balloon trousers and vintage denim to silk slip skirts and floaty dresses. There are barely-there leather versions, jelly styles, kitten-heeled flip-flops and beautifully minimal designs that look entirely appropriate for an evening soirèe. Still, I’d argue that the straightforward rubber thong remains the coolest of them all.
The key to making flip-flops feel styled rather than as though you’ve wandered away from the communal showers is all in what you wear them with. Let them provide an irreverent finish to something more elevated: a tailored trouser, an oversized shirt, a column dress or a full-length skirt. Add a good pedicure and a great bag, and suddenly the shoe once reserved for beach holidays becomes the most effortless way to make your summer wardrobe feel current.
It helps that flip flops are, mostly, genuinely comfortable. If you purchase the right pair (what this guide is for): no complicated straps, no breaking-in period and no pretending that a pair of rigid leather sandals isn’t slowly removing the skin from your heel. Simply slip them on and go. Here, I've weighed in on the pairs I've worn and actually found comfortable for wearing for more steps than are needed to get you down to the pool.
Ahead, the most comfy flip flops for effortless summer dressing, according to a fashion writer.Free People Going Coastal Flip Flops
Havaianas Slim Square Flip Flops
iQUSHION Ergonomic Flip-Flops
Nobody's Child Red Suede Flip Flops
Start with the straps. According to Marion Yau, podiatrist at Harley Medical Foot & Nail Laser Clinic, how they are attached can make a big difference to how long your flip flops last. “Avoid sandals with thin straps that are glued rather than stitched or moulded into the sole, as they detach easily and cannot be repaired.”
A slightly wider, securely attached strap may also feel more supportive, particularly if you plan to wear your flip flops for longer walks rather than simply around the pool.
How should flip flops fit?Your heel and toes should sit comfortably inside the edges of the sole, without spilling over the front or back. “Feet should sit entirely within the footbed, as overhang causes the toes to grip the sandal, straining the flexor tendons over time,” explains Yau.
It is worth trying on your usual size and one size up, as flip flop sizing can vary between brands. Your foot should feel relaxed as you walk, rather than as though you need to curl your toes to keep the shoe in place.
How often should you replace your flip-flops?Even a favourite pair will eventually lose its shape and support. Yau recommends replacing flip flops “once the sole has visibly compressed or the straps begin to fray, as worn-out sandals put unnecessary stress on the heels, arches and ankles.”
You should also consider the material, particularly if you plan to wear them around water. “Always check that the sole is fully waterproof or water-resistant, as a footbed that absorbs moisture creates a warm, damp environment where bacterial and fungal infections thrive.”
In other words, flip-flops may look delightfully low-maintenance, but keeping them clean, dry and in good condition is essential.
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