6 back-to-school fashion trends we’re seeing on the streets of Toronto

Back to school is finally upon us, and let’s face it: You tried to prepare yourself, but it didn’t quite work out that way. You’ve walked around campus or through the halls of your school and have definitely seen some people rocking cooler fashion than you.

Well, here’s a list of six back-to-school fashion trends you can try along with where to find them in Toronto.

Wide leg workwear

Wide cut pants have been popular for a few years now, but workwear has more recently made its way onto the fashion scene, and you’ll spot them all over every school campus in Toronto. It doesn’t matter if they’re cargos, trousers or canvas, the wider the better. People tend to pair these with high top sneakers that have an intriguing sole as that’s the only part of the silhouette that sticks out.

Dickies is a great wide leg option who focuses on more of a workwear aesthetic. Their garments can be found both in-stores across the city, as well as online. Urban Outfitters and Mark’s are just two stores that should carry the brand. For a more outdoor, gorpcore aesthetic, Patagonia’s King West location is chock-full of wide leg options for those who like their pieces on the more useful side of fashion – and with the company’s recent announcement, you know you’ll be supporting a brand with morals (a rare breed!).

Founded by Matty Matheson and Ray Natale, Rosa Rugosa offers similar workwear aesthetics to Dickies. After all, Dickies and Carhartt might as well be Matheson’s uniform. Their Gwynne pants do a great job of highlighting this trend with its chic outer shell and streetwear-style cut.

Matching athleisure

Looking cozy and fashionable is sometimes difficult to achieve. However, matching athleisure is a great way to maintain a fashionable status while still being able to fall asleep anywhere (a must when you’re in for a long day on campus).

Livestock is a great boutique in the downtown core which carries Parra, a brand which focuses on comfort as well as runway-level styling. Their matching tracksuits are always a great option, especially since the tops range from hoodies and crewnecks to three-quarter zips and more.

Reigning Champ also focuses on athleisure and thankfully, they have a location on Ossington. The brand is seemingly a cult icon in Toronto so get in on the trend.


When you’re walking around campus, the last thing you want on your feet is are bricks that hurt you more and more with every step. Crocs have had a revival in recent months, especially their newer platform style. And in the last week or so,  the brand announced they would be re-releasing their coveted Lighting McQueen clog for those of us with more eclectic style. You can find Crocs at the Nordstrom at Yorkdale or at the Vaughan Mills Crocs outlet.

For other clogs, check out Frock in Roncesvalles for on-trend styles, or Get Outside on Queen West for the comfy classics (Birkenstocks and more).

Funky side bags

Your backpack is important, but a side bag to carry all of your goodies will not only make your life easier, but will make you even more stylish. Lululemon’s side-cinch bag has blown up across social media platforms like TikTok due to a certain red colourway collecting huge amounts of money on resale platforms.

Herschel is a popular side bag option for those who like keeping their funds close to their chest. They offer student-friendly price points for bags which serve their purpose very well. However, for those looking to splurge, Due West carries a bunch of high fashion brands including Kenzo, And Wander, Moschino and many more.

Futuristic sunglasses

To help block out the negative vibes, Black Market Vintage, Cutler & Gross and Holly Eyewear are all great stores for sunglasses shopping around the city.

Black Market is known for their affordable prices and warehouse-style shop brimming with options (and the former underground storefront used to feature a barbershop and record shop). Now, the store’s location beside Aldo is constantly stocking up on vintage styles for all to choose from, including all kinds of sunglasses for $15 or less.

Cutler & Gross and Holly Eyewear both offer high-fashion sunglasses to make sure you look fly walking into school. The best part? Both locations have optometrists on standby in case you want to add a prescription lens on any pair.

Knit sweaters

Once fall rolls around, you’re going to be happy that you invested in a few knit sweaters. Cos is located on Bloor and has a fine selection of affordable knit sweaters for all sizes. The brand has been compared to Uniqlo in the sense that they produce extremely high quality basics for a relatively affordable price.

On the more expensive end, Italian sportswear brand Stone Island wouldn’t be where it is today if it wasn’t for their extensive selection of knit sweaters. Shop the Yorkville location for high-quality sweaters that are constantly tested back in the atelier’s hometown to give you that true Italian feel.

If you want a mix of both, head over to Nordstrom Rack where you can stalk the hangers and hope you pick up a designer piece for a good deal.

Article exclusive to STREETS OF TORONTO