What I usually do with outerwear is buy last year's stuff right as this year's stuff is coming out. I just bought a Special Blend jacket in August for about $200 less than it would've cost me had I bought it last January.
My favorite brands for outerwear are Special Blend and Four Square though. Grenade and Dakine make good gloves, not sure if you're considering those outerwear though.
Usually the bigger companies will have such a range of product that you'll be able to find stuff from one company in any price range, and you can be pretty sure that it will be good quality because a big company like that isn't going to risk a bad image on selling cheap ass stuff.
"Picture me rollin'"