What kind of weather, and are you looking for gear-type boots (think snow trudging and waterproof parkas)? I get my gear-type stuff from Moosejaw, Backcountry, or REI outlet. I have found good deals on pieces that are previous seasons' versions or closeouts.
For milder winter (wet, cold, but not a foot of snow) These aren't necessarily "sleek", but I like the weatherproof Vans MTE sneakers, and the Heston boot by Cougar. Both are insulated, waterproof, and provide great traction. Vans has a newer version of the MTE with a meatier sole, but I haven't tried it yet.