I'm not a good person to ask, because I don't have any experience with the premium boots - my experience is limited to the everyman's, big box store boots (Rocky, Danner, Wolverine, Irish Setter, Georgia Boot), which I've been happy with. But I will say that you probably need more than one, to match the weather. I like an uninsulated boot for early season, a 400 grams of thinsulate boot for Nov, an 800 gram boot for Dec-Feb, and a monster pac boot with felt lining or 1200-1600 grams of thinsulate for the really cold days - this one needs to be a size or two too big, to allow for huge socks or 2 pair. Behind insulation, a close second thing I look for is comfort - is it a contoured interior sole, or just a flat sole? How does it actually feel when you try it on? Third thing I look for is good cleats/soles - I like a very aggressive knobby boot, espec. on the front wrapped up around the toe, for climbing creek banks and such. Vibram sole beats no-name. Next I look for overall quality build / longevity. Is it top grain leather or just "leather"? How's the overall quality of the build look? Of course, price is also a consideration. Waterproof is really not much of a consideration for me, because (a) even the ones that aren't waterproof will keep out your basic dew and such, and (b) most importantly, if I'm expecting water, I won't be wearing a boot, I'll be wearing waders, or a knee-high rubber boot, not ordinary 6" or 9" boots.