Hipster hats can be tried, but you run the risk of being mistaken for an Obama supporter or a person in need of a shower.
A baseball cap is a miserable device for preventing the rain from
creeping down your neck, or in stopping the sun from blasting the same
location. Hats have brims for a purpose. Exploit them.
Outdoors, the further a hat comes off your head when meeting a woman
should be directly proportional to how beautiful you find her, or to how
much respect you wish to accord. For stunning creatures, the hat must come off completely and should
be lowered to waist level, held by both hands. For the earnest and
unkempt females who accost you on the street with a “Do you have a
minute for the environment?” your hat should remain firmly in place.
Unless you are “under cover”, i.e. armed and in uniform, for all indoor locations, take off the hat. Yes, even you.
If you don’t want to tip, don’t go out to eat.
…if you are an accountant, college administrator, manager of any sort, or
the kind of person who cannot identify a transmission, and you attempt
to wear a cowboy hat into a working-man’s bar, you may end up in a
fight. Which you will, deservedly, lose.
Read the whole thing; it’s everything a man needs to know about wearing a hat.