As with many other things, I think it's a matter of how you wear them. Certainly if you wear your cowboy boots with leather jeans and an untucked fitted shirt, it's an "urban/rock" thing. With denim jeans, you can go to from that extreme to serious cowboy (are they Wranglers, or are they Cavalli?), as well as the Lauren-esque American Classic (urban cowboy with tasteful restraint). With a suit, it's, howdy, Tex. With short-shorts, it's, hello, sailor. Considering how utterly ridiculous I'd look in a cowboy hat or on a horse, I'd say I'm closer to the urban/rock variation than any other. I wear the boots sporadically, depending on my mood, usually with denim, occasionally leather. (Not at all, lately, because I sprained my toe and it's still healing.) Sure, I'll wear them to work, but I'm a freelance techie who services mostly casual office environments and home users, so I can wear whatever amuses me (and my clients). In most circumstances, I would say cowboy boots do not provide ideal traction on the rungs of the corporate ladder.