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A good example is a fitted gray henley, black skinny jeans, and Chelsea boots

Might be ok, but Id suggest a loafer with a more casual shape wider, rounder rather than putting on a chunky sole On brown shoes being the same as the suit, yes that can be an issue but see the points in this article for ways to mitigate it

Are you doing the transitional season dressing thing yet
12 Long Cool Woman (In a Black Dress) Long Cool Woman (In a Black Dress) Producers Track 7 on Apr
