I've been wearing a black beret for about 25 years. There are very practical reasons for this: they are warm, they don't blow off in the wind, and they are a 'classic' style.
Quite honestly, I rarely go through a week when someone I've never met passing by says, "You look great in that beret." When I go to my local grocery store where people know me, if I don't wear my beret they have trouble remembering who I am. So I guess I've found the hat that fits my 'type'.
I teach at a fine and performing arts college. I wear the same clothes every day to class: kaki pants, turtle neck sweater (I have 50 of them, all different colors), sport coat, and BLACK BERET. This is my "uniform". There's only one day every semester that I change my attire: graduation.
When I get one of your berets, I soak it in cold water, then dry it in the sun or the clothes dryer to shrink it down to the 'style' I prefer. It needs to have just the right look.