It's not because your head is inherently un-baseball-player-shaped! I know of exactly one person who looks good in an off-the-shelf baseball cap, and that's frequent Cheer-Clubber and Box-poster Useless Tyler. Last time I saw him, his cap looked as new as the day it was stitched together, and just right on his head.
For those of us who aren't Useless Tyler, we need to break-in our caps so we don't look like locomotive engineers. Breaking-in a cap is a loving process that takes years of wearing it day and night until it takes on the contours of your own head. Well, some of us don't have years. Some of us want our hats to look good on our heads now, in time for the upcoming baseball season. I ran into this problem in May of last year, when my wife bought me a new home grey Jays cap for my birthday.
I was going to break it in the old-fashioned way, by wearing it and wearing it some more, and bending the brim a bit into a nice, pleasant curve, but after enduring two weeks of "New hat, huh?" and "It'll look better when it's broken in" from the regular goons up in section 518, I decided I needed to do something about it a little faster.
(By the way, the cap in question is a fitted New Era 5950, the "authentic" hat sold at the Rogers Centre Bullpen Store, and the same style of hat that most MLB teams wear on the field. If you're buying a sized Jays hat, you'll be buying one of these.)
First thing I did was to try to work in the front panel, which sat up very high on my head. Well, nothing happened -- the panel is designed to be stiff but flexible, and no matter how much I scrunched it or crumpled it, the panel just jumped back to the same shape it started at. I'll admit I was a little irritated by this. So I turned to that amazing repository of all information, The Internet. Hey, if The Internet can give me instructions on how to build the Millennium Falcon out of Lego it can tell me anything!
Almost anything. Google was not very helpful, turning up hundreds of blog pages of people complaining about how hard it was to break-in their baseball caps, but no solutions or instructions. I was despondent; I couldn't take another inning of razzing from the guys in the cheap seats. In my desperation I wandered all over the New Era website, reading anything cap-related, and I learned all about how many different New York Yankees caps are sold by just this one company...
And then finally, there it was, hidden in cleverly with the washing instructions. The 5950 cap is made of wool -- if you wash it in warm water it will shrink, so you need to dry it on top of something similar to the size of your head, like an upside-down bowl or a basketball (you know who you are) or your actual head. If you dry it on your head, it will shrink precisely to the size and shape of your noggin... Well, that's some mighty useful information!
I immediately leaped up from my desk at work and rushed to the washroom to soak my cap in warm water. Then I clapped it onto my head and waited for the magic to happen. After about ten minutes of wet-cap discomfort, I began to suspect that I was the victim of a savage burn laid upon me by the webmaster of the New Era website. Unpleasantly lukewarm water was tricking down my back and into my eyes. I began to plot my revenge. But then, as the cap dried, a miracle happened: the cap began to shrink down to the dimensions of my head, pulling the stiffened front panel backwards so that it no longer stood so high up.
And now, with some additional curving of the brim, I have a cap that's very comfortably broken in. I highly recommend this method, despite the few hours of discomfort and the wet dog smell that will trail you until you have a shower, and not out of some perverse need to burn someone else as badly as I was burned.