10 Of The Coolest Places To Check Out On Toronto’s Ossington Strip

Now that the weather outside is just starting to become enjoyable, why not celebrate with a stroll on one of Toronto’s best shopping strips? Ossington is packed with loads of fun food options, gorgeous shops, and everything in between. Eclectic and exciting, the Ossington strip is always a great place to be!

These are 10 of the coolest places to go on Ossington!

La Cubana

la cubana ossington styledemocracy
Instagram/@bigspoonfull

If you’re searching for the best Cuban sandwich in town, congratulations — you’ve found it! Not only is La Cubana on Ossington a charming Toronto staple, but it’s reasonably priced, too! Serving up all the classics like tostones, yuca frita, and their unrivalled pressed Cubano, this fun and lively spot is like taking a quick trip to Cuba without all the luggage!

MISFITSTUDIO

misfitstudio toronto ossington styledemocracy

Feeling a little ‘blah’ post-winter? Then head on over to MISFITSTUDIO. This one-of-a-kind movement studio combines pilates, yoga, and dance all into one soul-soothing workout. The goal at MISFITSTUDIO isn’t to work or tone your ass, but to work and tone your mind and soul, too. But trust me — just a few classes will have your behind looking booty-full!

I Miss You Vintage

i miss you vintage toronto ossington styledemocracy
Instagram/@imissyouvintage

Vintage shopping is pretty great, but designer vintage shopping is even better. If you’re anywhere near the Ossington strip, we can’t recommend enough stopping in at I Miss You Vintage. Known for being beautifully curated and in my opinion, priced really well, this is the place to go for pre-loved designer duds that are still of excellent quality. Don’t forget to poke into I Miss You Man for top designer vintage menswear, too. The best part? You can shop online and snag free shipping!

Superpoint

superpoint pizza toronto ossington styledemocracy
Instagram/@superpoint184

Ossington’s super fun and funky Superpoint, is known for their pizza, pasta, and wine and do they deliver on flavour, or what? Well known and highly revered amongst Toronto’s food scene, Superpoint is pretty much the place to go for inventive dishes like the Genoa Salami Pizza with Spicy Honey, and pastas like Duck Tagliatelle made with duck confit. If you’re looking for an eclectic, new spot for date night, this is it!

Tiger Of Sweden

tiger of sweden toronto ossington styledemocracy
Instagram/@tigerofswedenofficial

Stockholm-based fashion house, Tiger of Sweden strives to give men and women the confidence to be themselves through fashion. With a gorgeous modern vibe, this is the place to shop for updated basics with a unique and stylish twist. Expect to see lots of fun prints and cool accessories, too!

Anice Jewellery

anice jewellery toronto ossington styledemocracy
Instagram/@anicejewellery

Anice Jewellery’s goal is to bring your jewellery dreams to life through re-working vintage elements into one-of-a-kind items. Anice is committed to providing excellent quality to customers and it’s so wonderful to see how active the brand is within the community. The pieces available at Anice vary in style, with some being more delicate, and others that make a real statement. No matter your personal style, you’re bound to find something gorgeous when you step inside!

The Latest Scoop

the latest scoop toronto ossington styledemocracy
The Latest Scoop

Looking for a super stylish one-stop-shop on Ossington? Pop into The Latest Scoop and you’re in great hands. With fashion, home décor, accessories, beauty, gifts, and more, this breezy and beautiful boutique needs to be on your radar. Exquisitely curated, the items stocked here are of high quality and will add a chic touch to any space!

Sweaty Betty’s

sweaty betty's ossington toronto styledemocracy
Instagram/@jaliojeath

The Ossington strip is definitely a unique part of Toronto and if you’re looking for an eclectic spot to have a drink, step into Sweaty Betty’s. From the outside it looks a bit nondescript, but once inside, it’s fun, unpretentious and one of those places where they’ll tell it like it is. With a strict ‘no asshole’ policy, this LGBTQ+ space also has a beautiful patio in the back that should not be overlooked.

La Banane

la banane ossington toronto styledemocracy
Instagram/@labananeresto

One of Toronto’s top 10 restaurants is La Banane and its home is right on the Ossington strip. This unique fine dining hot spot is co-founded by master chocolatier Brandon Olson of CXBO and his wife, artist Sarah Keenlyside. Everything served is plated with the most finesse and care, but also (more importantly) tastes as good as it looks!

Peace Collective

peace collective toronto ossington styledemocracy
Instagram/@retailseen

Known for repping Canadian pride without being annoyingly stereotypical is Peace Collective. The brands flagship store on Ossington at Argyle is large and in charge with a cool industrial feel. One thing that is so important about Peace Collective is that it partners with charities and even hosts events with donations as entry fees.

Featured Image: Instagram/@toronto_laurin

Articles You May Be Interested In:
10 Cool Places To Check Out On Queen Street West
The Most Instagrammable Stores in Toronto
Beloved Toronto Denim Retailer Announces Massive New Location
14 Food Events Happening This Spring & Summer To Know About
7 Underrated Shopping Destinations In Toronto