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Neighbourhood Features: Ossington Avenue

In our Neighborhood Feature Series, we explore some of Toronto’s most unique and exciting areas, highlighting our favourite street style backdrops and local staples to help you bring your neighbourhood looks to life. This week we take a closer look at a Torontonian favourite, Ossington Avenue. Locally known for its cool-girl aesthetic, this area has exploded in recent years, becoming a new haunt for record stores, must-visit restaurants, pop-up markets, coffee shops, art galleries, and our favourite consignment store, I Miss You Vintage. Despite all the changes Ossington has seen, this street is still filled with charm and a unique sense of style, often showing locals in casual pieces with statement accessories, high style errand looks, and full glam moments for a night on the town.   

Whether you’re on your way to a park-hang, catching the 63 or going to Jimmy’s Coffee for a meet-up with friendsyou’ll want to go with something cool and comfortable without sacrificing style. A graphic tee, maxi skirt and vintage accessories are the perfect combination to complete the look.   

Headed to a meeting in the area? Keep it clean and casual in a button-up shirt dress and flats to look the part, perfectly marrying business and pleasure with a 100% cotton Xacus dress that will keep you looking breezy and effortless.   

Date night on Ossington is something special. With so many options to choose from you want a look that will be perfect for a dark-lit bar to a high-scale locale. The Kingston Dress by Greta Constantine is the perfect look, with a confident wash of colour and simple detailing that will make you look your best for that special someone and yourself!  

Going for drinks on Ossington is almost a right of passage in the city, being home to Toronto’s iconic Bellwoods Brewery. Their beer garden is almost always packed but if you can get a spot, it’s the perfect place to show your neighbourhood style in a statement top and on-trend denim. We love the Smythe Wrap Tie Top for its vivid colour and easy style. Pair with your favourite denim for a flawless going-out look. 

Need some guidance on creating the perfect Ossington Look? Book an appointment with a stylist to help you find the perfect look to elevate your everyday. 

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