my shoes since joining SF have been:
1) C&J Audleys in dark brown
2) Zee's Black black captoe, basically like the EG berkeley
3) Alden NST #8 Aberdeen (a gift)
I'm looking at getting a shoe with rubber soles(not sure what style yet), wingtips, loafers, and double monks in the future. If I were to do it all over again, I'd probably do the same thing, except I'd get rubber soles instead of leather on the zee's.
I definitely agree that having 3 nicer shoes would be...