I wore baseball caps when I was a kid. In those days, all you could buy were sized -- none of this Velcro strap at the back business. By the time I became a teenager, I stopped wearing hats of any kind except when it got really cold outside. In the Army, we had to wear hats or helmets when outdoors, the hat style depending on the uniform of the day and perhaps the wishes of the post or unit commander. On returning to civilian life, I again stopped wearing hats until around six years ago when I finally bought another baseball cap. With a Velcro strap.
(Actually, that's not quite true. After moving to Albany, New York I did buy a Navy watch cap for cold weather use. And once when I had a consulting project that involved a trip to Death Valley, California I bought a brimmed hat for sun protection.)
Back to baseball caps. After a while, the things became somewhat addictive. I'd buy them as souveniers or sometimes as personal statements. But for some reason I don't like to wear a cap that I don't relate to in any meaningful way. For example, I never attended Yale University, though I've visited Yale several times over the years. But to me, visiting is not sufficient association for buying a Yale cap. On the other hand, I bought a cap commemorating the Royal 22ieme Régiment Canadien Français
because I witnessed their flag-changing ceremony at Québec's Citadel (a ceremony performed once every few years). Clearly, I'm not rock-solidly consistent with respect to degree of association and caps.
Once nice thing about baseball caps is that they are pretty inexpensive souvenirs (current prices range around $10-$30, though couturier caps can set you back more than $200). Moreover they are useful, unlike other souvenirs that collect in corners of dresser drawers. My problem is that I now have lots and lots of caps, even after having weeded some out from time to time; how do I select a cap from my over-sized collection when I'm on my way out the door?
One selection criterion is the weather. I recently bought an Eddie Bauer cap that's been wax-treated, making it somewhat waterproof. So I'll probably be wearing it when it's raining. Another factor is what I'm wearing. I usually select a cap whose main color suits -- or at least doesn't clash with -- the rest of my wardrobe. That's one reason for having so many caps: I wanted a decent color selection to choose from.
Finally, there's the matter of the symbol on the cap; most baseball caps nowadays symbolize something or other. I do have a couple of caps bearing no logotype or slogan, so I can always wear one of these if I want to be truly neutral. Otherwise, it depends on my mood.
Since I live in Seattle, I occasionally feel like grossing out the locals by wearing a camo-pattern cap with the word ARMY on it. And if I'm near the University of Washington I sometimes get all snooty and wear one of my Penn caps. Other times I show solidarity: In Dukes's restaurant in Honolulu I might wear my yellow Duke's cap. Sometimes there are instances where I don't want to be misidentified. For example, I have a couple of caps with symbols relating to British Colombia and they also spot tiny Canadian flags on one side. Since I don't feel a need to apologize for being an American, I don't wear the Canadian caps overseas and run the risk of having people thinking I'm ashamed of my heritage and resorting to camouflage.
Clearly baseball cap wearing is a complicated subject. I'm interested to find out how cap-wearing readers cope.