The thing is, baseball caps have undergone a significant shift in their significance (in the Saussurean sense, as in "what they signify, how they act as signifiers") over the last fifteen or so years. I'll demonstrate mostly using a Yankees cap, though it pains me to do so as a Red Sox fan, because of the historical significance of the Yankees (or their logo, at least) in this particular story.
This started to change in the early-to-mid-90s, when Spike Lee approached New Era Caps (the company that makes mass-market caps for Major League Baseball teams), asking if he could commission a Yankees cap in red. This became a signature clothing item for Lee, and showed New Era that they could make much, much more money by decodifying what makes a Yankees cap a Yankees cap (and thus decodifying what a Yankees cap means, as I'll explain in a moment).
With the speed of anything marketed to and by the "urban" and "youth" markets, the change was immediate and highly visible: baseball caps no longer were locked to their 'regulation' colors, and a person who wanted his (or her) outfit to match the Yankees cap no longer needed to plan the outfit around the cap. Now it just takes buying a cap that matches the outfit.
As a result, the signifying aspect of the Yankees cap begins to chip away. That plaid Yankees cap could be a sign that you're a big fan of the team who is of Scottish heritage; it could also be a sign that you felt an item of clothing, ideally a cap, with those colors would best complete your 'look.' The baseball cap becomes about as significant as sneakers, which also have a community of collectors who are obsessed with acquiring the most outlandish, exclusive colors and patterns.
There's also a new submarket for "girl" caps, with any team's logo in white on a pink cap. We certainly couldn't have a woman wearing a plain Yankees cap, could we? How would we be able to tell she was female if she wasn't wearing a feminized version?
On a side note, there have been two mindsets with baseball caps for a long time; the 'urban' market (which is strongly correlated to, but not exclusive to, African- and Latino-descended people) often keeps their caps as clean and new-looking as possible, whereas the more hegemonic (white, mostly) portion of society tends to be a bit more comfortable with wearing "broken in" clothing (faded jeans, for example). This has led to pre-faded caps on one end of the spectrum, and flat-brim caps (with a different-sized brim, made to stay flat) on the other.
Those who buy the flat-brim caps do their best to keep them immaculate -- to the point that they're almost always worn with the stickers still attached. This serves two purposes, as far as signification goes: it says "I will only wear this hat so long as it is still brand-new" and also "this is a brand-name, authentic item for which the standard retail price is widely known." It's conspicuous consumption at its most basic.
By comparison, the 'broken-in' caps have bent brims, are colored with dye that fades quickly, and sometimes even come with pre-fab fraying on the seams. Affluent folks (and white folks in general, if I may perpetuate another stereotype) are more comfortable with dressing like they don't have any money.
In the interests of full disclosure, I should mention that I wear a more faded (mostly by being several years old) version of the Red Sox cap below, with the alternate logo rather than the standard "B" - I love the team (they were my hometeam when I grew up in New England) but much prefer NYC to Boston, and my hat sort of signifies that, I think.
Not particularly meticulous. Very Caucasian.
With so many other statements signified now, the team-specific signification of baseball caps is remarkably diluted, to the point where the caps are essentially decoration before they're a statement of team allegiance. They no longer only say "I like the team that wears this cap" - they also say "I like this color more than the color the team wears," "I have this relationship with consumerism," "I come from this ethnic background and identify myself as part of this social community," etc.
With that being the case, is it any wonder that the flat-brim caps of teams outside the region are starting to show up on teenagers as the finishing touch on obsessively color-coordinated outfits? If you like a particular color more than the colors of your hometeam, why not wear the cap of a team whose "on-field" colors match your outfit?
I can't imagine that the high-school-aged guy on my subway car last week, who was wearing a purple shirt, purple shoes, and a pristine, stickered Colorado Rockies cap, was wearing the cap because he was a Rockies fan. Certain teams other than the Mets and Yankees have fans in NYC -- the Red Sox are a notable example, as are some of the old teams based in Southern and Midwestern cities (the Braves, the Cardinals).
However, when I see several guys standing together on the L train late at night, all of them wearing Kansas City Royals caps which match the royal blue elsewhere in their outfits, I can't help but wonder if perhaps the cap is being used as a gang signifier. Perhaps it's urban legend that "KC" is used sometimes to signify "Killer Crip," but I'm pretty sure it's safe to say that there are more gang members in Brooklyn than there are fans of the Royals outside of Kansas and Missouri nowadays.
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