I've probably pedaled 5000 miles in mine. The ones with the fabric sides don't constrict the ankles much but the soles are heavy. I even went out and bought some nice Shimano cycling shoes but after wearing them once, I'm back to the boots. I don't like to ride in low top shoes because all of the sand and rocks that get in there. Also, I tend to go fast over rocks and dab a lot.
Anyway, my wife was a die hard chuck taylor wearer and we got her some good boots. Now, if we're doing anything outdoors, the boots are automatic.
Best of luck in your search. It will be interesting to see what you come up with.