Go to Sydney's on queen street. They sell clothing made in Canada and the fabrics are from Japan. Incredibly quality and fit. Brand is called united stock dry goods.
Overall, if you want quality clothing go there, Nomad across the street, Over the Rainbow in yorkville. Uncle Otis is nice as well.
There are more if you want recommendations.
I'm probably not going to afford the service anytime soon, but Sydney's made-to-measure service is a cool aspect of their store.
I actually think I stepped inside Sydney's once, but I wasn't really thinking about local brands at that time.
Queen west shops probably your best bet. The main Canadian stuff I wear is from Rudsak, it's aight but this year's offerings have not been to my taste. Too much cotton and fur.
http://www.rudsak.com/en/men
ya'll gotta do double egg at ryoji
That's a ways off from my usual attire, too much black, too much Generic Asian.
20 Canadian Brands Every Highsnob Reader Should Know. In addition to the aforementioned retailers on Queen street, also check out Haven and Gravity Pope. Are you interested in performance or fashion? Your priority determines what 'quality' means for you. I like tech so arc'teryx veilance is my canadian choice if I decide to splurge for 'quality'
p.s. some stores will be doing specials for blackfriday
Reigning Champ has some pretty nice stuff, but I don't know if I'd want to drop $100+ on basic wear.
I've seen Naked and Famous denim, but didn't realize they were Canadian.
On a related fashion note: I bought a coat from H&M, didn't really put it to any kind of stress test (arm movements mainly) and realized that it doesn't fit properly when I got home to wear it with stuff I'd match it with. Now I gotta exchange it.