Surviving for a quarter century is every business’ dream. It means that your store or brand has made a connection with the community, has continually provided stalwart customer service and always maintains an evolving level of excellence.  All of the above is true for Uncle Otis, the Yorkville-based boutique that just recently celebrated its 25th anniversary.

If you are a frequent visitor to the SD blog, you may know that we are big fans of Uncle Otis, they have appeared on our website as a “Store of the Week” and made our list as one of the best streetwear stores in Toronto.

Founded in 1991, the high-end menswear shop to this day focuses on providing Toronto customers with access to international street wear. Uncle Otis first rose to prominence in Yorkville by giving shoppers access to brands that were missing from the Canadian market. With superior collections from Wings + Horns to Universal Works to Norse Projects, Uncle Otis now carries over 30 brands that focus on quality craftsmanship and innovation.

With the anniversary of Uncle Otis’ 25 years in business, the StyleDemocracy team had an opportunity to head to Uncle Otis’ anniversary party at Airship 37 in the Distillery District of Toronto. Not only was the party attended by some of Toronto’s top fashion personalities and influencers, Uncle Otis also had their latest collaborative works on display.



The crew at Uncle Otis has  teamed up with some of their top-tier international brands to design exclusive collections that bring the 25th anniversary to life.

In our opinion, the crown jewel of the collection is the collaboration jacket between Uncle Otis and Canada Goose ( which deserves it’s own post).


The 25th Anniversary Travers jackets marks the third piece between Uncle Otis and Canada Goose. An all-black treatment with a solid black upper body with a herringbone black quilted bottom, elbow patches, a 3-way front pocket system, hidden zip breast pocket, and side seam zips. Trust us it’s beautiful.

25 years is a big deal, so Uncle Otis also worked with three other amazing brands creating unique and useful clothing perfect for the Uncle Otis Customer.

The whole 25th anniversary collection collaborates with Maharishi, Tanner Goods , and Universal Works.

The Maharishi Pant crafted by  the London-based environmentally-focused designer, Maharishi has crafted  a pant  fabricated with specialized 3xDry fabric. With anti-fit silhouette, elasticized waistband, high-end Swiss-made RiRi zipper, black nylon leg hem, and 25th-anniversary embroidery, the trousers are specifically designed for everyday fall and winter wear (without tear) in the city.


When working with Tanner Goods, Uncle Otis decided to offer a selection of high-quality products.  Hand-crafted by Tanner Goods in Portland, Oregon, the utilitarian-collection includes a belt, lanyard, wallet, and valet tray. For the first time ever, Tanner Goods has made this collection with exclusive charcoal leather fabric and matte black hardware lightly embossed with Uncle Otis’ custom stamp.



Lastly, Uncle Otis teamed up with Universal Works to created a fabulous utilitarian jacket.  David Keyte, Universal Works co-founder and designer, has worked alongside Uncle Otis to craft two exclusive jackets with custom charcoal wool exterior and quilted olive nylon liner and reversed. Designed with a varsity neckline, the jacket is the perfect fall-wear weight or layering piece in the winter.

“We couldn’t be more pleased to be celebrating twenty-five years of bringing Canadian and international clientele hand-picked clothing and exclusive collections,” said Donnell Ennsowner of Uncle Otis. “While we’ve watched the fashion landscape and industry evolve, we’ve always maintained our dedication to consistently sourcing and selling only high-quality contemporary men’s fashion pieces.”



Visit Uncle Otis online for exact product launch dates and further product detail. As always shopping local is one of the best ways to spend your dollar, especially at high-quality retailers like Uncle Otis.