These are all sweet deals. Just got the Churchills in Cognac in 8.5 from Paul Stuart for $249 and I thought that was a deal... until now. Love them and they fit like a glove, but the thin channeled sole started separating from the rest of the soles after 10 hours of normal wear. Should be an easy fix so hopefully not that big a deal. 8Ds need to grab the both the cognac and blacks. Eyeballing the gator loafers in 9. How old is old enough to pull these off (norht of 30, south of 40, but when I bought tires today for my car, I chose the best combo of treadwear / performance over straight up performance if that tells you anything)? Rider - knowing that the Churchills in an 8.5 fit me perfect all around - tighter than most of my shoes - would the 9Ms fit me or would the heels flop around in your estimation?