The return of the ugly shoe—and why it works

The fashion world has long moved back and forth between the polished and the peculiar, and in recent seasons, the momentum has clearly favoured the latter. Welcome to the era of the “ugly” shoe, where bulky comfort has quietly become the prevailing trend. Have they, like Tabis before them, gone from being misunderstood to cult classics?

From the resurgence of jelly sandals to the unexpected return of Wallabees, these footwear choices have everyone raising their eyebrows. Here are seven shoes that do just that. 

Heeled flip-flop

The heeled flip-flop, a nod to ’90s beachwear, has officially made its way into everyone’s wardrobes. Thanks largely to the designs of Reformation and Totême, it has become a must-have in every minimalist’s closet (hello, Sienna Miller). Although it might seem too casual or somewhat unattractive, its versatility is undeniable, working well with both casual and formal attire.

Jelly shoes

Jelly shoes, once a ’90s staple, have made a major comeback after being spotted on The Row’s Spring-Summer 2024 runway. These transparent, often glittery sandals are water-resistant, easy to clean, and have been seen on celebrities like Jennifer Lawrence and Emma Roberts. They remain a personal favourite.

Ballet trainers

Ballet flats have evolved into the ballet trainer. New and improved? That’s up for debate. Combining the charm of a classic ballet flat with the comfort of a sneaker, the style was popularised by Chloë Sevigny in ECCO's 2025 campaign.

Clogs

Clogs used to be associated with healthcare professionals, but high-fashion houses have since reimagined them. Swarovski has even collaborated with Crocs and has made an appearance at this year’s Met Gala. Did it follow the dress code? Not really. 

Fisherman sandals

First worn by Hailey Bieber, fisherman sandals are gradually finding their way onto more feet. With their open-weave design, they’re breathable, somewhat stylish, and now seen in both urban and coastal wardrobes.

Wallabees

Clarks’ Wallabees have seen a resurgence in popularity, thanks in part to a collaboration with Tyler, the Creator. Once considered a classic dad shoe, they’ve since found favour with a new generation.

Boat shoes 

Once reserved for yacht clubs, boat shoes have been reimagined for the fashion-forward. Spotlighted on Miu Miu’s Spring/Summer 2024 runway, they’re now making waves well beyond the marina.

As the ugly shoe trend unfolds, it’s clear that in the world of footwear, the most unconventional choices often make the most compelling statements.

Lead image: Getty 

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