Sometimes a random thought leads me down a rabbit hole. This is one of those times.
After the New York Yankees defeated the Cleveland Guardians in the American League Championship Series to reach the World Series against the Los Angeles Dodgers, I mused on social media, “a world series matchup for the girls who rock fashion ball caps.” It was an off-handed joke referencing the popularity of both Dodgers and Yankees caps among today’s street-style fashionistas.
And I started to wonder, how did those caps evolve from function to fashion?
Plenty of baseball caps have logos that are pretty simplistic and don’t overpower an outfit or one’s personal style. But how specifically did the Yankees and Dodgers logos become singular fashion caps?
So I went straight to the source.
“The first cap we made for a major-league baseball team was in 1934 for the Cleveland Indians,” New Era brand historian Jim Wannemacher told the Chicago Tribune. “And then we picked up a couple teams — mostly regional to us. We’re out of Buffalo, New York. The story goes, as we picked up a team, we have yet to lose it as a customer.
“The original fitted hat was an unstructured, kind of raggedy hat that we were making throughout the ’30s, ’40s and ’50s. And in 1950, Harold Cook, our second-generation owner, created the 59Fifty style, which was a much different cap. It had a structured front so that the logos were always pointing forward, and kind of our whole goal there was to create uniformity across the league because prior to that, most teams were buying their own caps from their local guys and every team wore something completely different.
“So our end game, up until 1994 when we got exclusivity, was to create a product that all baseball teams could wear proudly.”
In the 1990s, thanks to hip-hop artists and the proliferation of street style, New Era saw its hats grow into a must-have item. They were no longer just hats for baseball players. Fitted caps — especially Dodgers, Yankees and Chicago White Sox caps — became bigger than their respective locales. They started to symbolize more than loving a team or being from the area. They became iconic.
But in 1996, the hats leveled up again, Wannemacher explained.
“It was right around this time film director Spike Lee was going to a World Series game in 1996 and it was the New York Yankees versus the Atlanta Braves. He called our owner, Chris Cook, and asked if it would be possible if we made him a custom red New York Yankees cap. And our owner kind of laughed and said, ‘Well, no, we can’t, because our agreement says we can only make a dark navy hat per the league license.’ And then he also asked, ‘why would you want a red Yankees cap?’ Because allegiance to a color, to a team, for fans is paramount, especially when you’re talking about the New York Yankees, because that cap has always been the same. So now you get a red hat, which is the same colors as the Boston Red Sox and the Atlanta Braves and all these other teams, and it’s almost like anarchy to propose to wear another team’s color. That whole thing was kind of puzzling to our owner, but he said he’d have to call the league and the team and get an okay with them,” he said.
“So he called both Major League Baseball properties and (George) Steinbrenner and they both said, ‘yeah, go ahead. One cap. No big deal.’ We made it for him, shipped it to him overnight and he wore it to the game. He was sitting behind home plate and somebody took a picture of him wearing it and the next day, basically all hell broke loose because now there’s a product out there that nobody was ever able to make before that is now being made. And that just basically changed our business overnight.”
From there, it took about a year for New Era and Major League Baseball to hash out an agreement to begin making licensed baseball caps in colors other than team official ones.
“It opened the door to, wait a minute, maybe there’s a bigger opportunity here for us to do non-on-field product or non-authentic product and sell it as a fan custom fan product, where we can do pretty much anything you want with it. Now you could express yourself individually based on the color or the material we made it with, or whatever,” Wannemacher said.
As fitted and other styles of caps became popular in fashion, New Era saw baseball logos, due to their clean, timeless style, become less about baseball and more about style. Not long after Lee’s hat debuted at the 1996 World Series, the brand started receiving forecasts of colorways from sneaker companies. Fans were matching their caps with their shoes and New Era was not only aware but decided to help by making more and more colors available.
“You can wear a Yankee or Dodger hat with pretty much anything, unless you like being super bold, but culturally, for the outfit, I think it represents success. It projects confidence. They have flexibility and easy color bases to build off of. I think that both of them play in pop culture in different ways,” said Randy Wilkins, director of ESPN’s “The Captain” documentary and a Bronx-born Yankees fan.
“The Dodgers cap became a representation of the West Coast. It’s evolved from being a piece of LA to representing an entire coast, community and culture just because it was adopted by Compton and like all those neighborhoods as their own. There’s a long relationship between the hats and hip-hop and Black culture.”
Rich Palmer, a brand marketing professional, agrees.
“It is synonymous with fashion, but then you have that extra layer where it’s like, ‘Yo, I’m from Brooklyn. I’m wearing a Yankee cap because this is what represents me.’ I’m from LA. So whenever I travel, I wear my Dodgers cap to let folks know I’m from LA,” Palmer said.
“There’s two different layers which I think all come together because think about Black culture, we create the trends, we drive culture. And I think we’re taking what was originally a performance hat that was on the field, and we made it something special to us, to represent us from, where we’re from, and how we express ourselves.”
“Black folks are known for taking things and we make it cool. And I think that’s what happened with these hats. We took something that traditionally, that Babe Ruth wore, and Mickey Mantle wore, and we brought it into a part of the culture, and everybody followed suit.”
But in recent years, the caps have undergone another evolution. They went from everyday casual style to being complementary accessories in elevated street style.
Ticara Devone, a street style and sneaker content creator from the West Side of Chicago, said baseball caps have become viewed as less about sports and are treated the same way as a luxury brand hat with a logo — particularly among women.
“I would say now that it’s really part of every girl’s wardrobe staple right about now, if you were to go on TikTok right now, you will see a girl in a Yankees cap, a silk skirt and Adidas Sambas or Puma Palermos,” she said.
“I think we’re kind of moving out of that very casual look and I think the girls are starting to turn the heat up a little bit as far as dressing goes. We’ll see a girl in a sweatsuit. They may have their sweater or cardigan wrapped around their neck with their Yankee or Dodgers hat on with some sunglasses and their latte. But also, I’m seeing this high-fashion version of it. That’s where we’re going with the hat. It looks top tier, expensive.”
The fun thing about caps becoming fashion accessories is that while we now see them in various ways off the field, they’ve maintained their credibility. Typically, when something grows in popularity it becomes scarce. Instead, baseball caps are widely available and while everyone wearing a cap might not be connected to a team, the caps never lost their original audience — baseball fans.