5 of the hottest fashion trends on the streets of Toronto this fall

The weather is shifting once again, and it might just be our favourite temperature to dress for in Toronto. And what better way is there to get inspired than with Toronto’s emerging fall trends? Here are five fashion staples you’ll be spotting on the streets of Toronto this fall, according to some of the city’s best-dressed. 

Moto boots 

Courtesy heelboy.com

Motorcycle boots have been gaining traction online in recent months, and are clearly here to stay. In fact, of all the trend insights sourced for this article, moto boots was the one mentioned by Torontonians the most. They’re a fairly heavy boot characterized by a low heel, and often adorned by buckles, though they can be found in varying lengths: ankle or below the knee. The TikTok fashion influencers say a key styling tip is to pair a moto boot with a red jacket for optimal coolness. Alternatively, fashionista and vintage seller Maya Wohlfahrt, also known as Space Cowboy Maya, advises pairing these heavy boots with delicate fabrics like silk or lace. Heel Boy on Queen Street West has a great selection of moto boots in varying styles, or if you prefer to shop secondhand, Common Sort is likely to have a few in rotation.

 Jackets instead of hoodies


Fashion lovers are predicting the “death of hoodie culture” in Toronto streetwear this fall. Menswear is going to adopt jackets over the hoodies we’ve previously seen incorporated into transitional weather outfits, and we can see why! With prep wear and other elevated trends on the rise, this layering season calls for a touch of class. Whether it’s traditional denim, corduroy, sportswear, trenches or blazers, there are a ton of options to add a finishing touch to a fashionable outfit. For a designer look, you can check out Cameron Alastaire Vintage, a new menswear-focused vintage shop on Queen Street West.

Midi skirts over pants 


Spring 2023 saw the resurfaced trend of dresses over pants, which references the pervasive Y2K fashion that gen Z have been flocking to. One might say that it’s old news, but this fall is seeing a more specific variation: midi skirts over pants, with particular attention paid to denim midi skirts (as seen in the work of Toronto stylist, and Editor-in-Chief of Bully Magazine, Bobby Bowen) along with pleated midi skirts.

Toronto digital creator and plus size model Oriana Doan says the key to modernizing this trend is contrast. “It’s not just a matter of placing a skirt over top of pants,” says Doan, “you have to be creative.” 

The midi length of skirt is ideal because it can be easily repurposed — worn higher or lower, layered or twisted to create an asymmetrical visual. If it has a slit, even better! You can strategically position the slit to showcase more of your pant leg. 



 Following the preppy fall trend, Torontonians are expecting to see more tweed incorporated into streetwear. Doan says she’s all for it because tweed is a “timeless and classic” material, but it doesn’t have to look particularly studious or feminine either. Though her favourite iterations are the pink tweed pieces from the Chanel Spring 1993 ready-to-wear collection, Doan says tweed is more versatile than that.

“It can be adapted into different personality types depending on how you style it, or the colour palette of the tweed,” she says. If you like the ’60s mod Chanel vibe, try lighter colours like pastels, paired with pearls, ballet flats and headbands. If you prefer an edgier look (think Vivienne Westwood), Doan recommends a red and black tweed skirt paired with an oversized white button down, a leather jacket and moto boots.

Sporty knitwear 


Freelance stylist Karensa McCarthy has cozy athletic apparel on her fashion radar this fall. Considering the recent popularity of integrating sports jerseys into fashion, it only makes sense that we welcome cooler weather with the kinds of pieces you can wear both in and out of sports mode too. Consider logo-adorned crewnecks, varsity sweaters and cozy knits combined with athletic accessories like track pants and sneakers. Brooklyn-based knitwear designer from Toronto Lindsay Vrckovnik recently collaborated with Nike Women to style outfits of this exact nature — colourful knitwear paired with functional, athletic pieces. Vrckovnik’s own custom line of knitwear includes knit track pants and jackets adorned with jersey numbers.

Article exclusive to STREETS OF TORONTO