I have shoes that I wear for riding and I wear my clogs otherwise. I don't think I would ever ride in my clogs - although I do sometimes see commuters doing it. My shoes for riding all have about the same thickness in sole and I ride grip king platforms; the slight difference in thickness is easily offset by the ability to move my foot around on the large platform. Once a year (spring) when I buy new riding shoes I make a seat post adjustment and that's it - I have a brooks saddle and locking seatpost and saddle bolts instead of quick release.