I paid $40 for these direct off the Steve Madden website. I think they are worth $40, maybe $50, but not more. Their insoles are thin but not totally uncomfortable. The leather is distressed, so if you like that look, these boots are for you. The grey color is more greyish/brown, which is also quite nice and matches all sorts of pant colors. As far as sizing goes, I am a standard 13D, and these boots are a little big on me, but not too big. They look awesome. You can wear these boots with a pair of jeans or as part of a business casual outfit.