I really like my North Face Bridgeton boots. They look and feel like pretty normal riding boots, but they are insulated (they're nice and toasty) and weatherproof. They've held up well to snow/salt/cold/etc.
With ebates/coupons/etc. you could probably get them below $125.
Mine are a deep purple but this year it looks like all they have are white and black.
They aren't bulky like most winter boots but keep you dry and warm. I wear them with leggings or skinny jeans in the winter and not only do they serve their purpose but they look like nice too. I have a pair of clunky Sorels too but I would never wear those for a day doing errands. These are so damn comfy and cute I do it all the time!