I've been wearing the same pair of Wolverine work boots for years. They're very comfortable. They are, however, getting a bit long in the tooth. I saw some Triumph boots (over the ankle) that I liked. They looked to be made of some sort of nylon/acrylic. They were fairly light.
$3.00 pair of flip-flops to go along with my $300 helment.
Seriously though, I worn a pair of Carolina knee high, steel toe motorcycle boots for almost twenty years. They've been resoled so many times, i've lost count. The right boot actually has a hole in the toe to the steel from an accident. Bigern