I bought a pair of Chippewa's a year or so ago because they look great (and already have started to develop a wonderful patina) , and they make me sound like a bad ass when I walk around (REALLY loud thud when I step). God awful in slick condition's but I love them, I wear them with jeans in the autumn.
I've ridden bike's since I was a kid, but I'd never wear them when riding, not enough flex at the ankle when using the tran's and brake (I mainly ride sport bike's).