$80 · Nearly New Men's Sorel Waterproof Boots (Kezar size 12)

They were purchased for me by my girlfriend, and I've worn them maybe four times (just to a restaurant). In the end, they're not really for me. They're easily the most comfortable boots I've ever had, but friends and family keep saying they're very, "Rich-looking". The leather's very nice, but I'm just a weathered Timberland Premium guy - don't wear boots like this. They're $220 brand new, and the soles aren't even broken in, so $80 and they're yours.