Join Date: Feb 2004
Location: St Peters, Missouri
Bikes: Rans Rockst (Retro rocket) Rans Enduro Sport (Retro racket) Catrike 559, Merin Bear Valley (beater bike).
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Actually, I have a friend who attached a pair of cleats to the soles of some combat boots for winter mountainbiking.
I've never done it, but I would expect to have a problem with the example that you gave. Most shoes are made by glueing the upper materials onto a board that becomes the sole. They aren't designed to withstand continually pulling upward on the upper. My bet is that the shoes would quickly come apart.