I think I get it (or at least can justify it). The theme of Mike Lowell's fundraiser was "A Night at the Copa". The Copa was popular in the 40s and 50s. With those blue eyes, Jason Bay wasn't going to pass for Sammy Davis Jr. or Dean Martin. And what Frank Sinatra impersonation would be complete without an iridescent fedora? At least, I hope that's what he was going for and that that hat is not a part of his everyday going out wardrobe.
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