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My hat goes on when I wake up and it doesnt come off till I go to bed. I had a operation on my head when I was 2 months old (cranial syntosis). Surgeons cut slits in my skull to make my head grow right, I was born without a soft spot. Without the operation my head would would of grown into the shape of a watermelon or football. I have a half inch wide scar that goes across my head, from ear to ear and hair does not grow on it. Since I like to have my hair under and inch length, the scar is always visible, and thats the reason I wear a hat. Right now I have 3 or 4 hats I wear; Kenworth, Winchester, NAVY (thanks stroker_deezel) or Ford Racing.
If I'm not at work, I'm wearing one. Usually a Ranger Boats cap or a Dallas Stars cap. Hides my receding harline. I wear an old camo Winchester hat when fishing. That thing is nasty but I never wash it, might wash the luck out of it....
I've got a whole bunch of hats, but rarely wear them. I just don't really like wearing them much anymore.
Used to wear them a lot, but it just got to the point where anything on my head got to be too warm.
I will suck it up and throw one on if I'm working/fishing out in the rain.
Also, I always preferred to wear them backwards, as I don't like anything blocking my field of vision (I only have one eye that works as it is, lets not cut down the visibility any more than necessary...).. And since oversized white boys tend not to look the best with a ball cap on backwards, I just don't wear one.
And I keep my hair very short also, so, I've got nothing to hide.
Usually wear a cap, except when not socially acceptable. If nothing else, a cap serves as a sweatband and the equivalent of cat's whiskers (the bill is sort of a warning system that my face is too close to something). It seems hats (other than cowboy hats) went out of style about the time of mandated head restraints in cars.