You absolutely pull that off!!What's the old saying? You know you are old when your presence with the opposite sex is more cute than threat!
Ps, if you want compliments, wear a bowler. I get compliments all the time from both men and women.
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If I tried people would think I was being ironic.
I'm comfortable in flat caps (and only because a brilliant salesman at Laird in London made me wear it out and not to take it off for a whole day)... just need to ease into crowns, a bowler being the end goal.