In honor of the World Series, which will likely be won by the Cubbies in two more swinging victories, it’s important to address the rampant misunderstanding and mis-wearing of the classic american baseball hat.
Case in point:
Pictured here is Kylie Jenner, daughter of Kris and Caitlyn Jenner, wearing a baseball hat. Does Kylie like baseball? Unclear. She certainly likes kickball.
Kendall gets a pass here because she played baseball on the Gap team as a child.
Liking baseball is clearly not a prerequisite for wearing a baseball hat, but it’s a good place from which to start, because that’s why baseball hats exist. Because of baseball. According to the internet and the New York Times, The New York Knickerbockers, arguably the first organized baseball team ever, first wore straw hats to games, to be proper. And then they started wearing a tighter newsboy style, probably because it was more conducive to running. But it was technically the Brooklyn Excelsiors, also known as the Jolly Young Bachelor Base Ball Club, who first wore the closest thing to our beloved baseball hat. That was in the late 1850s.
Note the first young man, perking an elbow and sneering to his team—he’s holding a classic baseball hat. Same with the man second to the end, minus the sneer.
A sporting attitude and a sense of freedom were required, then, to wear the hat. You weren’t wearing a silky top hat or a work hat; you were having fun, and the hat didn’t indicate that you were either rich or poor or much else besides that you were sporty and fun. In the baseball hat, you were just a guy. (Also that: you had to be a man.)
Kylie Jenner breaks a few of the classic baseball-hat-wearing-rules, and that’s why she looks crazy in her stupid baseball hat. Yea, she’s a woman, but we’ve been allowed to wear baseball hats since at least the 70s. The reason baseball hats look bizarre on Kylie is because she makes it her job to look rich 101% of the time: by putting on a baseball hat, by putting on the “comforting image of classlessness,” as Troy Patterson of the New York Times puts it, she’s trying to disappear into normalcy. Not possible. Plus, it doesn’t look like she’s having any fun! And she definitely still looks rich.
Kylie Jenner wearing a baseball hat becomes a case of sticking out rather than blending in, and the same holds for Kylie’s baseball-hat-wearing fans.
To trace this modern trend back a few years, see: Paris Hilton, Britney Spears, Posh Spice. None of these women were ever able to disappear, and they might have been classless, but not in the right way. All of them had fun, but usually not in a baseball hat.
Even in the context of normcore, the normalcy of a baseball hat is rendered the point, and therefore iconized, not democratized. That ruins the point of baseball hats.
These days, lots of men wear baseball hats that suck. In fact, if you’re a guy, it’s really easy to wear a baseball hat that sucks.
They suck for various reasons, and most of the reasons have to do with lazy faux athleticism. Or faux “vibes”, generally speaking (like men’s athleisure jogger pants). The men’s baseball hat has become so diversified in design and quality and label that it has essentially replaced the daily ties we used to make fun of; now, office-less men are using baseball hats to look both busy and fun. The looser the connection between your hat and any particular brand or movement or thing, the cooler you are. In fact, the cooler the hat, the harder to tell exactly where it came from. Again, not the point of a baseball hat.
You get it! Here’s Justin Bieber, the nail in the coffin of the casual baseball hat. His problem also relates to fit and attitude; it’s all wrong.
Of course there are a zillion exceptions to all this, including if you’re a real fan of actual baseball and you wear a fitted hat representing your team; if you’re a baseball player; if you’re one of those old guys who wears a trench, New Balance, and a Yankees hat while carrying a briefcase; if you’re Rihanna; if you’re Lauren Hutton from the 70s.
Lauren Hutton looks great in this baseball hat.