I imagine, though, that most big cities would be an odd place to see someone wearing boots on a first date. Unless your dating profile says you're a grammy-winning country star, in which case, anything goes.
*Slightly related tangent: Being both a geek and a gearhead, I've used the downtime at my shop to conduct various car studies. My shop has large glass windows pointed directly out at a busy highway that melds into Main Street in my town just a few blocks away from my shop, and I've tracked all of the vehicles coming & going for multiple days. 46% of the non-commercial vehicles were trucks (as defined as any vehicle with an open bed), and while I don't have the exact numbers in front of me, I believe the ratio of SUVs/CUVs/full-sized vans to cars & minivans for the remainder of the vehicles was about 3:1. Pretending to be macho isn't even optional here, it's mandatory. Being a fan of small Japanese imports puts me in about the smallest automotive minority; I think there are even more European cars in our town than Japanese.