Sadly I know what you mean about selection in Ottawa. I score the occasional deal at the Bay in Rideau, when they have their end of season 50% off the already reduced pricing, especially good for shirts. Same stacked discounting stratgeu at Banana Republic for some causal wear. Harry's is good when they have their end of season sales on ties, pick up a few Zegna and Canali for $40-50. Consistently best pricing during their sales would have to be at E.R. Fisher. Got some Facconable pants from them for $49 last sale. Benton's at 240 Sparks also has very good end of season pricing. Picked up a jack Victor suit for $400 this spring
But I have to say that I make a few trips a year to the US to score the biggest deals, either Woodbury or major cities like NY or Chicago . The savings kind of pay for my vacations. Best deals this past year include 3 pairs of Boss oxfords for $69 USD each, Boss isn't exactly the best, but for less than seventy bucks for made in Italy whole grain, who's going to argue. Picked up a Corneliani blazer at Bloomingdales for $260, marked down from $1295. Boss jeans for $40. Incotex pants for $80. Also get no shortage of ties for less than $40 from Zegna, Drakes. Even picked up a Boss tie for $18 on my last trip. Tod's loafers for $170, Ferragamos for $260. Pink shirts for $32. Boss suit for $200. In general, I find that the prices are slightly better at retail stores during sale weekends, like upcoming Black Friday, than they are at the outlet malls.
Compare these to Harry Rosen or Holt's pricing, and you see what I mean about the savings paying for my vacation. I just go visit Chicago or NY whenever I need some new clothes.
To be honest, the B&S here at SF is very hit or miss for me. But I have had a lot of luck on Ebay.