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What's the best shoe in terms of quality money can buy in the $ 150-300 ballpark?
C & J (upper part of your limit).
Used? I haven't seen a new pair for this price, but then again I wouldn't know exactly where to look.
Rebadged Brooks Brothers can be had quite easily.
Not for $300. If so really really old and beat up.
On a related note, where do you fine gentlemen find your discounted Aldens and C&Js?