Buying good stuff matters but I certainly wouldn't pay a lot for it and there is little need for cycling specific gear for many applications. I like cycling tights. Neoprene booties are awesome. You could try nashbar brand, REI outlet and Sierra Trading post for reasonably priced cycling tights and booties. There is no need for cycling specific gear for the upper body IMHO. There I'd shop around for the best deals. Pile isn't expensive and works well with some sort of shell. Layering is the key and there is nothing you need for cold weather that costs a ton of money. I think some of the prices for cold weather cycling are obscene.