Nope - I buy whatever is on sale. I've got college logo hats, "cigar" logo hats, some Callaway hats, etc...
I hang the hat from the bag and use the same one every round until it doesn't look good anymore. At that point it turns into a lawn mowing hat, and I grab a new one for golf.
Depends which hat I'm wearing - I've got caps for my irons, driver, golf club, a visor that matches my irons, a Roots golf flat cap - I wear whichever one I fancy on the day. Often I wear the visor and have a cap handy in case it rains.
No! Make that hedoubletoothpicks no!
It doesn't even match my clothes half the time. I usually wear a golf hat that came from a golf course. I buy one if I play somewhere and wear it until I get sick of it, the dog eats it or my wife tells me it no longers has enough fabric to be called a hat.
When I was an even worse golfer than I am now (15 hdcp), my incentive for breaking 90 was this: If I break 90, I'll commemorate the grand occasion by purchasing the course's cap. Had to stop because I accumulated too many caps (I can break 90 more often than I can wear out caps... but not much). So I wear golf-course caps, plus a couple of USGA caps I've got.