I own a cheapy straw hat (working on getting a nicer, better shaped one), a cheapy black felt hat, and a cheapy brown felt hat.
Last night I discovered I own a $160 dollar platinum felt hat..and that I have had it for like 6 years.....whaaa?!
The black felt and the straw are my two show hats for the ranch horse shows. I am far from being a "cowboy" (mainly the BOY part lol) but heck. Everyone starts somewhere!:) Plus, the black hat is also my drill hat. I think black is quite snazzy looking and sharp...specially with a sparkly crown OMG SPARKLES!

DD
The Brown felt is by far my favorite..the shape works really good for me, as does the brown since I have brown eyes:P I wear it everyday to work, and tend to dress it up with a flower like a lot of the girls at the shows do.