At this point, your needs will exceed your savings/income. YMMV in outlet shopping in the GTA. In that price range, try Tom's in Kensington Market. It's wearable til you can afford better. Suits at the Rosen and HR outlets will bump into your top end and be mainly Coppley or something like that. You might find Boss or the odd Samuealson for $600. Even at the outlet, the stray Zegna would be double that unless their is a huge sale going on. One more caveat, most of the discounted suits you will find will not usually be in the classic patterns, you might have to be flexible as long as it is blue/ grey. When I was starting out, I had a windowpane suit, it became known as the "clearance sale" suit because the joke was that all of the suits on sale were checked and if you had one, you got it on sale.
Those outlets usually have decent dress shirt deals, couple of white, whole lot of blues, the odd striped or pink one. They have some decent deals at Brooks Brothers often. Doesn't hurt to browse now and then.
In Toronto, even at the high end, you are pretty much SOL on dress shoes. Try the AE guy on the B/S. Best deal on AE I've found is Rego, at about $299 Boxing Week with a small but wide selection of the better AEs. Below that it's absolutely a joke. I'm willing to spend, but other than AE and the odd Ferragamo, it's forget it. EG and BB are recent to the city and pass your price point. Wear in the ballpark cheapies or go online. Don't forget a couple of ties, especially if you only have a couple of suits. Get real ties, those BR jobs are excusable if you're starting out, but after a while, they don't cut it, along with the cheap looking printed ones from the department stores.