As others have said above, you'll find no love for penny loafers with suits on SF, although it is a pretty common look among East Coast trads. For everything else, from chinos to flannel trousers and a blazer though, penny loafers are great. In addition to the Randolph, you might check out the AE Patriot. Got a pair from shoebank recently for $200 and have been very pleased.
12/17/14 at 9:04pm