If there is something that YOU like then you should do it regardless of what others think. But me personally, I have never liked a man in a baseball cap. To me it screams - I am an assclown.
But then again - it is MY preference. Who knows? I could be wrong about what the look screams, but I know that I dont like it on a MAN. It just looks very boyish in my eyes.
I have a dynamite body and look extremely young but there are many outfits I refuse to wear because I am so not 17 (though many 17 year old girls should bury their heads in shame) nor do I want to be.
I wear hats often because I like to keep the sun out of my eyes and face. I look very good in them. I feel ya on the not having to wash your hair thing. I love to ride with my sun roof open and windows down so a hat keeps my hair out of my face so I can see to drive. LOL Not to mention very few women wear hats. I prefer to get attention with one of my signature hats than to have my tits and ass hanging out. I could if I wanted to but I just dont feel the need.