Seasonal change is upon us. Warm days are turning into cool nights, and golden hues of fall foliage are emerging from green, while cohorts of students are heading back to school downtown. The weather is changing drastically from day to night, making dressing yourself a little bit of a challenge. But there’s no shortage of street fashion to take inspiration from, and if anything is clear, it’s that layering is the go-to strategy. From elevated track pants to funky jackets and still more polka dots, here are the fashion trends you can expect on the streets of Toronto this fall.
Go elastic
Sportswear is a mainstay in Toronto’s fashion scene, often woven in with urban aesthetics that give the wearer a comfy-chic appearance. Sporty pants, paired with crisp shirts, leather jackets or blazers, and statement accessories, subtly imply that a person is a hustler — on the go from one occupation to the next, all while maintaining an effortless composure. This season, they’re appearing on the runway in this exact manner. The Tams Pants by small batch-made brand Tams are exactly that: black and wide legged with an elastic waist band. They were made “for living comfortably while still feeling put together.” The first batch sold out quickly but a waitlist is going for the next set.
Aviation outerwear
@rachelpiccone ooooo workwear bomber @Uncle Studios ♬ Cherry – Jordan Susanto
Round silhouettes have been making appearances on Toronto’s runways and streets, infusing outfits with an immediate sense of intrigue and power. One way to adopt the visual allure while putting together a classic look is the good old aviation-inspired bomber jacket. The waist-length outer layer is perfect for layering pieces underneath or contrasting against more sleek structures like skirts and tall boots. The Workwear Bomber from Ossington’s Uncle Studios is made from 100 per cent cotton so it elicits a relaxed feeling, coupled with the classic ribbed elastic waistband, and embroidery detail on the collar that gives it a creative touch.
Patch it up
Patchwork pieces are arguably a fall staple. A longtime mouthpiece of bohemian style that first became popular in the late 1960s/early 1970s, the aesthetic leans into the maximalist trend that has maintained its popularity in Toronto, while signalling a thoughtful DIY nature. Pinterest’s 2025 Fall Trend Report backs this up, reporting that searches for “patchwork clothing” have skyrocketed for the fall season, with users searching for items like patchwork sweatshirts, jackets and T-shirts. Heirloom textile brand Honeybea, now sharing a shop in Kensington with vintage brand Vintage Baby, is the go-to destination for colourful patchwork garments in Toronto, like the Berkeley Coat or Plough Skirt. Independent upcycling designer Kaleb Savoie is also accepting commissions for custom work, including patchwork garments.
Pervading polka dots
Another top indicator from Pinterest’s fall fashion trend report is the polka dot aesthetic, searches for which have surged on the platform by 699 per cent. Fittingly, it’s also the featured print of local brand Ahiri‘s Fall collection, featuring silk skirts, dresses and collared shirts adorned by tiny dots (in shades of black, beige and white). The pieces are described as balancing polish with whimsy, and are shown accessorized with matching scarves. As a long cornerstone of French fashion, the aesthetic is evocative of iconic fall looks from famous French fashion inspirations like Jane Birkin and Brigitte Bardot. Popular expressions of the trend include dotted accessories (bags and scarves), hair accessories like scrunchies and even dotted manicures.
Head to the prairies
The perfect sartorial expression of romantic autumn weather, the prairie dress is extremely versatile for the season. Doubling as a transitional weather hack as much as a standalone piece, the garment can be worn alone or layered for warmth with tights or pants underneath and a jacket or sweater over top. An oversized leather jacket or a long trench provide a fun urban contrast that makes the look feel distinctly Toronto, while the traditional qualities of the garment — like a high neckline, ruffles and full skirt — feel feminine and nostalgic. You can buy them secondhand at shops like Siberia Vintage, Exile Vintage, or Souk and Silk vintage. Simons (newly opened in Toronto) and Canadian brand A Bronze Age offer some more modern takes on the prairie dress, if full ruffle isn’t your style.
