On “Empire State of Mind,” JAY-Z rapped, “I made the Yankees hat more famous than a Yankee can.” It’s a stunt, a boast typical in hip-hop that need not be examined literally. But he was on to something, even if he alone isn’t solely responsible for the ubiquity of the Yankees fitted. It’s bigger than a baseball team, somehow bigger than 27 World Series. Even for natives, it’s bigger than root, root, rooting for the hometeam. That logo and that hat have come to represent New York City as a whole, a wearable point of pride and symbol of aspiration that’s spread across the world. On this episode of “Why It’s Cool,” we’ll examine how part of a team uniform became one of the most iconic accessories around.

The interlocking “N-Y” insignia was originally designed by Tiffany & Co. as part of a medal given to John McDowell, an officer of the NYPD who was shot in the line of duty in 1877. To this day, no one knows exactly how, but the Yankees adopted it for themselves in 1909, when they were still known as the Highlanders. This was four years before they’d become the New York Yankees.

The logo on the hat is actually slightly different from the one placed on the chest of those iconic pin-striped home jerseys. On the hat, the “N” and “Y” are roughly the same size, while the jerseys uses a logo with a larger “Y” and blockier letters with more exaggerated curves.

The Yankees fitted as we know it today came into existence in 1954, when New Era first introduced the 59Fifty. It’s still the market leader and official cap of the MLB to this day, and has only undergone slight changes over the years. But it largely remains the same, maintaining all the familiar lines. Mark Maidment, the Senior VP of Brand at New Era, explained the significance of the switch to the now-timeless silhouette.

“We stiffened the front of the cap. Up until then, caps were very soft. So the logo kind of crumbled. It didn’t have that premium beautiful canvas for it to be perched on.”

Still, baseball caps were mostly relegated to the field until the ‘70s, when they became more acceptable in everyday life. In Ball Cap Nation, author James Lilliefors attributes this to several factors, including the increase in televised sports and Tom Selleck rocking a Detroit Tigers cap in Magnum P.I. This made it seem more cool instead of quirky.

Spike Lee, whose image is inseparable from the Yankee cap, is the reason why baseball caps are available in anything other than the team issued colors. In 1996, the director wanted a red Yankees cap to match his red Yankees jacket. With the approval of Yankees owner George Streinbrenner, New Era obliged. When he was seen on television with the new red cap during the 1996 World Series, consumer demand exploded, and the flood gates were opened for a range of colors from pink to camouflage to just about anything you could imagine.

Maidment touched on the story, which he said is told monthly to this day in the New Era offices: “As soon as we did the red Yankees cap it was suddenly like, we can do loads of different colors. Let’s disrupt this thing, and MLB saw that as a great innovative move for them as a league. As soon as that started happening of course, then it comes with the hook up. You could hook up the colors with the trainers, with the sneakers.”

To learn more about what makes the New York Yankee cap such an indelible style icon, listen to the full episode of Why It's Cool.