I wear a pair of combat-style boots from Sears, $29 with a nicely padded ankle. They look a little too clunky to wear in nice restaurants, etc. when I out with the wife on a Saturday night so I picked up a pair of Justin Ropers -
10" boot, low heel
They are quite simply the best shoe/boot I've ever purchased. I had them on all night the first time they were worn and my feet never felt more comfortable. The only downside is their leather sole. BUT, I discovered for the princely sum of $40 you can get the same boot with a rubber sole which would be perfect for bike wear:
Justin Basic Roper's I'm tempted to get a 2nd pair just for bike wear.
