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Strange, was your boss addressing you as a superior? That is, we'd like to see you dressed more work appropriately since you represent the company, etc. Or was it more of a friendly conversation between two guys (assuming male boss) and he was just relating his take on your look.
Yeah, I would dress a bit differently to go out to a bar than I would to go shopping or just around the house. Not necessarily dressed up, but smart casual look. I too like to present myself well, but part of that for me is to not be overly formal. I'm not a stiff, formal kind of guy, so I don't dress that way unless it is really called for.
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