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.:D

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
 
boots

I have these, very comfortable for all day riding and even walking around between rides.
Had them 2 years now and still holding up great.
 
Oxtar now called Tech something or other .. BIKE UK magazine rated their gortex boot the best of 60 boots they tested .. excelled in every area.
 
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