A fashionista’s guide to the best shopping on Ossington

I Miss You Vintage 

For those who are always on the hunt for the hottest finds from past seasons, I Miss You, Inc. should be the first stop on your treasure hunt. Owner Julie Yoo’s eye for authentic, one-of a kind items include haute couture runway garments by top designers, rare vintage finds like a 1997 Chanel quilted backpack or a 1920s Louis Vuitton trunk, and special limited edition items that were previously sold out in-store or purchased abroad and were never sold in Toronto.

I Miss You’s main women’s boutique offers shoppers three rooms of carefully edited all designer label items against a simple white background. Glass showcases display smaller accessories, jewellery, and high-end designer purses. Its men’s boutique has a more antique and rustic setting where shoppers can find contemporary designer label items set against antique Victorian display cases, industrial factory carts, taxidermy, and turn of the century barn-board wainscoting.

I Miss You, Inc. has also quietly become a favourite of celebrities and designers including Lady Gaga, Iman, Miley Cyrus, Alexander Wang, Alexander McQueen and Michael Kors. Whether for a 1989 Chanel vintage bucket bag or last season’s Balenciaga dress, I Miss You’s items are chosen for their condition and relevance to today’s fashion market. It is the destination that consistently carries a large selection of in-demand brands, in part because I Miss You has the best consignors and fashion-savvy clients that regularly cycle through their clothing and turn to I Miss You to sell them. Shoppers can expect to find something new every day, and consignors can be confident that the owner’s extensive background in the fashion history allows them to expertly identify, edit, authenticate, and appraise their items. I Miss You, 63 Ossington Ave. 

Part of the carefully selected men's footwear offerings at Lost & Found.


Lost & Found 

From day one, not only has Lost & Found stocked hard to find streetwear and classic menswear brands, they have also worked on building a community hub. Most famously, they’ve housed a coffee shop in-store from day one, an attraction that draws people in and encourages them to stay. Lost & Found also organizes an annual summer outing to a Blue Jays game for friends and customers, occasionally hosts gallery events for other artists to showcase their work and photography, and even housed Town Barber’s shop in the back of the store until they found their own spot at Dundas and Ossington. It’s safe to say these ventures have not only expanded their clientele, but garnered them many new friends.

But Lost & Found has never forgotten how to seek out great clothing. In the fall/winter, Lost & Found will be receiving a few pieces from Carhartt Work In Progress, a line from Europe that is a modern interpretation of the Carhartt legacy. Using workwear as a reference point, WIP gives the brand an updated feel in cut, quality, and material ($25-$375).

Viberg is also a relatively new brand to Lost & Found, but has been making footwear in Canada since 1931. The storied Canadian boots range from $695-$825, and they are guaranteed to last in both quality and style. Lost & Found, 44 Ossington Ave. 

Some of the streetwear selection at Jonathan+Olivia.



After a successful debut in Vancouver, Jonathan + Olivia’s seven years on Ossington has turned them into a Toronto staple. Fashion savvy men, women, and even children, who love keeping up-to-date with the garments that are sashaying down the runway, have no doubt fallen in love with the wares that bridge the gap between modern design and timeless style. 

Most recently, Jonathan + Olivia have tapped into a new wave of emerging young designers like Jacqumeus, Off-White c/o Virgil Abloh and Vetements (all 2015 LVMH Prize finalists), who bring forth a directional point-of-view, while still maintaining its focus on core collections like Isabel Marant, Alexander Wang and Acne Studios. The store has also taken notice of a few Canadian designers who have been lighting up the fashion world. 

“We’re excited to feature collections from some great Canadian designers including Sid Neigum, Horses Atelier, and D.L Eyewear,” says owner Jackie O’Brien Jones. “Sid has been making headlines for his expert draping and edgy aesthetic – his wrap dresses are a client favourite. Horses Atelier is loved for its easy dresses and loose silhouettes. (The overalls and linen jumpsuits have a cult following!) The D.L Eyewear sunglasses are super stylish (who knows cool frames better than Dan Levy?) and a great price point – every frame is $95 CAD. We’re also excited to be bringing in some new Canadian jewellery lines later this summer, Beaufille and Lauren Klassen (Lauren’s line will be exclusive to J+O in Toronto).”

And it’s not just the customers who have taken notice of Jonathan + Olivia’s well curated collection, it’s the designers as well. When J+O first opened the Toronto store seven years ago the space was only used to house its collections. However, thanks to its loyal clientele they’ve been able to expand its business and grow the entire space. “We like to do renovations every six months or so,” says O’Brien Jones. “I think it’s important to keep things fresh and exciting!” 

Over the years, events have ranged from Alexander Wang’s temporary one day takeover event, to a party with the aforementioned Dan Levy, to various cocktail parties for Toronto Fashion week. But in the end, it is the fashion that keeps J+O a mainstay and destination shop on the Ossington strip.

“Fashion changes, but my philosophy and buying direction have always remained the same. We buy collections that we like the aesthetic of and collections that my husband Nic and I want to wear, but always part of the brand vision for J+O. And less is more, " says O’Brien Jones. “Ossington Avenue and West Queen West have an awesome community vibe – we’ve partnered with our neighbour CAMH for fundraisers and in-store events. Giving back to the community is important to us. We’ve been able to remain a destination location because Toronto continues to support our vision. It’s that welcoming, neighbourhood feel that keeps people coming back.” Jonathan + Olivia, 49 Ossington Ave.

Article exclusive to TRNTO