people who have squared masculine foreheads looks worse with hats on, people who have more rounded ones (in terms of men) look better
the biggest factor however, is your jaw shape as a man, if your jaw is pointer and not wide, you look worse with a hat on because it will highlight this immensely, i only figured this out after wondering why i look so bad with hats on, my head shape is essentially a pentagon with a round chin, so hiding my squared forehead makes me look worse because of how my chin is
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