In a city as dynamic as Toronto, it’s easy for travelers to fill their days (and their suitcases) by wandering in and out of shops and making a few purchases as they go. On the city’s streets, you’ll find everything from designer stores to beloved local labels, wellness outlets to souvenir shops. So in this guide, we’re focusing on the best neighborhoods and districts for picking up unique mementos and clothing items.
Located near Toronto’s Chinatown, this just might be one of the most unique “markets” that you’ll ever come across. Kensington Market is actually a small neighborhood whose streets are lined with coffee shops, restaurants, bars, storefronts, and plenty of other small businesses that are well worth your time. But the market’s abundance of vintage and secondhand clothing shops is perhaps what it’s best known for. So, whether you’re looking for a statement piece, a wardrobe staple, or even a Halloween costume, you’re guaranteed to find something one-of-a-kind here — even if you have to do a little bit of digging first.
And although the neighborhood is a lot of fun throughout the entire calendar year, it’s at its very best during summer weekends, when plenty of pop-up vendors set up shop in the streets. On warm Sundays, Torontonians flock to Kensington Market in droves, transforming any shopping trip or brunch into a block party. It’s an experience unlike anything else you’ll find in the world’s major cities!
Located in the city’s west end, Ossington Avenue runs for several blocks, and with its boutiques, restaurants, and above-average concentration of ice cream shops, this street makes for a great Saturday stroll. If you’re hunting down upscale (read: designer) vintage clothing, you’ll want to stop in at I Miss You, and if you’re seeking out high-quality menswear, then Lost & Found is the place for you. Shoppers with a hankering for graphic tees, patches, buttons, and other accessories shouldn’t skip a visit to locally owned and operated Crywolf. Plenty of additional shops line the sides of Ossington Avenue, but if you’d like to pick up a Toronto-centric souvenir, our last recommendation is the perfect place to do so. At Peace Collective, you’ll find clothing items and accessories embellished with slogans like “Toronto is Home” and “Toronto vs. Everybody.” And you can even feel good about those purchases: for every item that you buy, Peace Collective will donate five school meals to a child in need. See you on Ossington!
Queen Street West
In 2014, Vogue named this thoroughfare as the second coolest neighborhood in the world, citing its “indie patisseries, homegrown labels, and hidden-from-view galleries.” And although several years have passed since then, Queen street still lives up to the hype.
On warm days, you’ll share the street with hundreds of Torontonians, all intent on eating a tasty meal or picking up something interesting. And between restaurants like Aloette (a comfortable neighborhood bistro) and Soufi’s (a Syrian café), and stores like Common Sort (another secondhand clothing shop) and Cocktail Emporium (a perfect stop for aspiring bartenders and amateur mixologists), you’ll quickly see why the street draws such a large crowd.
The newest hub on this list, Stackt only opened in April 2019, but it has quickly become a much lauded, highly appreciated stop for both locals and visitors. By attracting shops, pop-up stores, restaurants, and a large brewery, this former plot of unused land has been transformed into a lively, interactive retail space. But there’s a twist: the developers built the space by stacking shipping containers on top of, near, and next to each other.
As you walk in and out of storefronts, stopping occasionally for a coffee or craft beer, you’ll probably be tempted to spend more money than you should. After all, the entrepreneurs who have set up shop in the area (whether on a permanent or temporary basis) are extremely passionate about their trades and creations, and their enthusiasm is contagious.
Stackt is pet-friendly, so you’re likely to see a large number of dogs happily exploring the space and relaxing on the nearby lawns with their owners. And since Stackt is also extremely pop-up-friendly, you’re never going to find the exact same shopping scene here — making the hub an excellent place to revisit on your return trips to Toronto.
If you’ve worked up an appetite after all that shopping, you might want to check out our guide to Toronto’s international food scene. And if you’re eager to explore the city from additional viewpoints, make sure to read our guide to Toronto for every traveler. Happy shopping!
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