For my tastes the _most_ classic shoes were made by G. Bianchi. (That's _G_ Bianchi who have no relationship as far as I know to Bianchi the bicycle manufacturer.) These were extremely well made, although they already looked "retro" in 1989, when I bought my last pair.
I have no idea if they're still in business but it's possible that someone like Larry Black, Mel Pinto or Sheldon Brown would still have a few pairs in the basement.
Jill, you were taking inventory of shoes in Larry's basement - did you find any of these shoes? Fred Rednor - Arlington, Va.
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