Originally Posted by KitAkira
All RWs are workwear-oriented. The Gentleman Traveler (1911???) is the dressier model but it's still a bulky silhouette.
Yeah, I'd start thinking outside of Redwing if you want something dressier. Epaulet (an affiliate - see clickable banner at top of screen) has some really nice boots right now and you might get a SF discount still, but I'm not sure. Those Thorogood horsehide boots look awesome (p2)http://www.epauletshop.com/servlet/t.../23/Categories
Also, check out the 'Streetwear shoes and boots' thread here for more ideas.