Thanks for the honest opinions, everyone!
I actually do have a big preppy streak in my style, believe it or not. I like subverting the conservative look, if that makes sense. I have a bunch of toppers from Abercrombie, Hollister, and LL Bean and I personally think my sleeveless collared shirts are a bit preppy.
Vildy, I DO see what you mean about them seeming like liars. Like a rugged brown would be more practical and "honest." I will keep that in mind for sure - and I'll think about that when trying on those tall, white, cracked leather boots, too! Something to chew on. The glam-ness is a little less in person for the silver shoes, I'd say. The shine is much more subtle.