This “ugly shoe” trend is taking over Toronto and it’s kind of perfect for winter

From Uggs to Moon Boots, this trend might be perfect for winter 

The winter season across Toronto warrants some frosty new trends. In recent years, we’ve seen the emergence of balaclavas, and other seasons have made us obsessed with long-standing trends like puffer coats and leather pants. This season, “ugly shoes” have dominated.

The trend is generally defined by traditionally unflattering shapes and styles. A natural spinoff of the 2020-era dad sneaker: New Balance, Asics and Saucony had a field day when it came to getting consumers on their sneakers. And rightfully so. These brands have been long-time royalty in the department of comfortable athletic wear. And with fashion trends shifting towards more functional and athletic styles, it only made sense that these three would reign supreme.

In the world of fashion lovers, Adidas became a favourite for its slew of collaborations with creative design teams. For one, the Adidas X Yeezy 700 in the Wave Runner colourway was a favourite among celebrities due to its chameleon-like ability to blend into any outfit. These comfortable, functional (read: not that pretty) shoes led the way to the trend that is taking over footwear: ugly shoes. Think everything from high-heeled Crocs to Moon Boots to the famous Maison Margiela Tabis.

This season, Ugg has ruled the scene and came back into style after being deemed off trend (cheugy, anyone?) for years. Spotted on the runway and on street-style icons such as Bella Hadid, the low-cut, flatform sole and slipper styles have made a comeback  — and we’re willing to bet it’s because they’ve leaned into the ugly shoe trend.


Their Tasman Puff slipper, which is its own emerging trend, is a streetwear take on their usually simplistic suede slipper with a lined interior. The same slipper has also been winterized, wrapped in vulcanized rubber, and given a little sock the same way Nike has added to their soccer boots in recent years.

Ugly shoes embody a developing fashion ethos that embraces the ugly in a subversive way, along the lines of “so bad it’s good” thinking. Styles that are traditionally considered unappealing have taken over the runways, from clashing patterns to “grandpa” sweaters to ill-fitting shapes, and ugly shoes are next in line. The best part? Some of the on-trend ugly footwear out there is perfect for winter.


We’re looking at you, Moon Boots! Snag your own at TNT Fashion, or slip into the perfect ugly Ugg at SoftMoc or Sporting Life to wear around the house or out and about all winter. Or stray off the beaten path and visit Getoutside to find the ugly shoe that works for you — the Malvados puff daddy mule might be a strong contender or Hunter’s insulated short puffer-style boots. This season, stay on trend by staying really, really off trend. Your feet will thank you.

Article exclusive to STREETS OF TORONTO