I've got my eyes on a pair of Timberland Earthkeepers but I'll be honest, I have zero fashion sense. I was thinking I'd pair them with some jeans and... and... I don't know what, but something. http://www.shoes.com/p-ec1002092.shtml If you check out the rugged first date that's kind of what I'm thinking of putting together. Opinions? http://www.menshealth.com/style/dressright/ While we're talking rugged fashion, what are your opinions on brown bomber jackets? I've got a Johnston & Murphy one that I love, but I've read mixed reviews on the whole leather jacket thing. Someone said the jacket and boots was trying too hard, and then suggested a preppy outfit which, to my mind, is trying too hard. Doesn't suit my personality at all. The jacket and boots just seem right to me. But then I am trying to dress to impress women, and if a leather jacket is just plain tacky I'll hang it up when I'm on a date.