I never thought of myself as a hat person at all. I'd always liked how women looked wearing them (though I mostly saw these in magazines and on TV), but I always felt self-conscious when I tried them on in stores every few years: "Oh, my head's too big!" "Oh, people will just think I'm being pretentious if I wear one."
Part of that discomfort stems from living in Texas for so long. In winter, it only rarely gets cold enough to even need a hat, so there's not a huge market for them. You can find 'em in malls and in boutiques, but that always involved a special trip and paying 50 bucks or more if you wanted something beyond your basic knit cap to keep the wind out of your ears. Aside from pure utilitarianism, women in Austin, where I'd lived from 1983 to early 2007, just usually didn't wear hats, unless they were college funksters. In fact, the whole time I was in Austin, the only hat I ever owned was a brown fedora that I'd bought at a costume shop back in the mid-'80s when I was trying to dress up like Garbo for Halloween.
New York City, though, is a whole other story! Forget my laziness about shopping and my unwillingness to spend much: Once October hit, the street vendors and cheapo shops were stocking hats en masse---just walking from the subway stop to work in the Union Square area, I'd pass at least 15 different venues with hundreds of different hats to choose from: berets, fedoras, cloches, charming Himalayan pom-pon hats, and hats I don't even know the names of! In every sort of fabric and color, and the most expensive I found seemed to be $20, though most were $10 or less. These hats really were in my face all the time (figuratively, not literally, at this point), so I couldn't help but notice them.
And then as the weather turned cooler here, the women (and men, too) started decking themselves out, and I couldn't help but notice THEM! Little old rich ladies in their cool-looking cloches with jeweled pins (and their corresponding little old rich men in their dapper felt fedoras); funky girls in their Himalayan and Oliver Twist caps (and their corresponding funky boys in their Sinatra/Tom Landry/Pete Doherty plaid hats tilted cockily back on their heads); "regular" gals and guys in their knit caps and hats with furry flaps to pull down over their ears just because it was COLD; not to mention the big tall furry Russian-looking things that I've seen on a few heads!
It's a darn CIRCUS OF HATS, I thought to myself. And that's the cool thing about a circus---there's no need to feel self-conscious since everyone around you is quite in their own world, doin' their own thing, with absolutely no inclination or desire to stop and figure out if what everyone around them is doing is the "proper" thing...You just DO it.
So, inspired by the streets o' NYC, and after years of being "bunged up" about hats, I finally stopped being paranoid and started buying some damn hats for myself! (The first two I do wear weekly; that cowboy thang I bought for Halloween---my coworker was "Bret Michaels" as seen on VH1's "Rock of Love" and I tagged along with him that night as "Rodeo"! ;p)