Weekend Wear on Ossington Avenue

Gap cropped jeans, Club Monaco blazer, Telfar oxblood bag and Cole Haan mules on Ossington Avenue in Toronto

Believe it or not, I don’t spend a lot of time on Ossington Avenue.

I live on the East End, and years of pandemic movement restrictions has kept me from exploring Toronto as much as I want to (I moved here in 2019 and was working towards my bar admission right up through May 2020). Now that I have some stability, I’m very excited to find new-to-me places in the city!

With that, I was really excited to visit Paris Paris, an open-air wine bar on Ossington a few weeks ago with my friend, Lauren. After some rosé, oysters and literally the most delicious butter I’ve ever tasted, we went for a little stroll.

Gap cropped jeans, Club Monaco blazer, Telfar oxblood bag and Cole Haan mules on Ossington Avenue in Toronto

Dressing for a weekend outing is always fun for me. I like to use my work pieces with something a little more casual, like jeans and a tank. This pair of jeans from Gap is my go-to. I love a high-rise pair and the cropped leg is great for my height (I’m 5’2”). I bought this pair in 2019, but Gap still carries a similar fit, and in petite sizes! My tank top is a basic Airism camisole from Uniqlo. I love these because they’re so comfortable and are super easy to pair with something more elevated.

Speaking of elevated, I wore a thrifted Club Monaco blazer. I will wear this to work occasionally - usually with my trusted black dress - but was excited to try this in a more casual look. It was sunny, but not too warm, so the wool-blend blazer was perfect for the weather. The white piping along the collar and pockets makes this a little more fancy than some of the other blazers in my closet.

Gap cropped jeans, Club Monaco blazer, Telfar oxblood bag and Cole Haan mules on Ossington Avenue in Toronto

My bag is the Telfar Medium Shopping Bag in Oxblood. I got this through the Bag Security Program, which is how I would recommend most people get a Telfar bag. It comes around a couple of times a year, and keeps the bags accessible. (EDIT: As of June 7, Telfar will no longer be doing the Bag Security Program after June 2023).

My shoes are Cole Haan leather and suede mules. These were purchased at Nordstrom Rack, which has sadly exited Canada (along with Nordstrom proper). I wear these shoes to work a lot, but they work just as well for walking in the city. They’re very comfy!

Finally, there’s a funny story behind these sunglasses. When I was in Tampa last month for my sister’s bachelorette party (more on that here!), we spent a post-brunch afternoon in Hyde Park Village to do some shopping. Being Florida, it was extremely sunny - but I had switched purses and forgotten to pack sunglasses! I hastily purchased this pair from Francesca’s (which we don’t have in Canada!). They were pretty cheap, but I really like them! I love a pair of tortoiseshell glasses, and the cat-eye works really well for my round face. I’ll probably be wearing these for the rest of the summer.

Vintage Louis Vuitton handbags at I Miss You Vintage on Ossington Avenue in Toronto

I finished off the afternoon with an iced latte and some macarons from Delysées Luxury Desserts and visited some of the new and vintage clothing shops (including I Miss You Vintage). I can definitely see myself spending a lot of time on Ossington this summer!

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