Stylin' On 'Em: The Pop Culture History of the Yankees Cap

Image via Complex Original

WHEN: 1877–1922
COMPLEX SAYS: The design history of the world's most recognizable sports logo goes back nearly 150 years. Originally designed by Louis B. Tiffany, the interlocking "NY" insignia first appeared in 1877 on a medal given to John McDowell, the first NYPD officer shot in the line of duty. The New York Highlanders, as they were then known, began sporting the logo in 1909, and by 1922 the solid navy and interlocking "NY" became official design of the New York Yankees cap. With an estimated 20 million caps in circulation back in 2003, you think Tiffany's fam has seen some kind of compensation? We hope so. #wherethecashat #gimmetheloot

WHEN: 6/21/1990
COMPLEX SAYS: While on his campaign to end apartheid in South Africa, the recently freed Nelson Mandela made one of his stops at Yankee Stadium. As he concluded his speech, Mandela had Mayor David N. Dinkins place a Yankees jacket on his shoulders, then donned a Yankees cap, saying: ''You now know who I am. I am a Yankee.'' One of the world's most prominent peace figures aligning himself with a franchise that would come to be known as the Evil Empire? We have no problems with it. FOH, jealous Mets fans.

WHEN: Late '90s–present

COMPLEX SAYS: From his "Hawaiian Sophie" days to his button-up shirt movement, Jigga has had a pretty diverse style history. But through all of his looks, his biggest fashion staple has been the Yankees fitted. From the "Do It Again" video to lyrical references in songs like "Empire State of Mind," no other rapper has associated himself with the Yankees more than Jay-Z. Sorry, Joey Crack.

WHEN: Late '90s–mid 2000s
COMPLEX SAYS: Back in the day, the Limp Bizkit frontman who claimed to smash Britney Spears and beefed with Em, could always been seen rocking a red Yankees fitted. During the band's heyday, when albums like Significant Other and Chocolate Starfish and Hot Dog Flavored Water (most pause-worthy album names coming soon) were going multi-platinum, legions of fans could be seen donning the cap. By the look of things now, the 40-year-old Durst may want to start sporting fitteds again. #justsayin'

WHEN: October 2000
COMPLEX SAYS: During the World Series of 2000, mayor Rudy Giuliani had no qualms about publicly displaying which team he was rooting for. The Brooklyn-born Giuliani supported the Yankees by wearing the navy fitted throughout the series, despite the fact that the Yankees had already won three of the previous four World Series titles while their crosstown rivals had last brought home a championship in 1986. We're not mad at homie for being honest, after all, a Yankees cap is a much better look than his cross-dressing antics several years later. Yikes.

WHEN: 2000–present
COMPLEX SAYS: According to the New York Times, since the turn of the century, over 100 suspected New York City criminals have worn Yankees apparel during crimes or at the time of arrests. Some have even attributed the hats popularity among criminals to Jay-Z. Right, FOH. We're not trying to be fashion police, but we'd hate to be stuck up by anyone rocking this atrocious joint. On second thought, scratch that, we'd hate to be stuck up period. #keepit100

WHEN: Mid 2000s–present
COMPLEX SAYS: One of the biggest pet peeves among sports fans is seeing people at events wearing sports apparel that in no way relates to the city, sport, or team on the field. So, when some see Denzel Washington at a ton of Laker games donning the black-on-black Yankees fitted they may have the same facial expression as Pauletta Washington in this photo. But dude is a two-time Oscar winner, takes in eight-figure salaries per film, and he's a New York native. Do you, Denzel. Do you.

WHEN: April 2007
COMPLEX SAYS: In this ESPN ad, which still runs today, Big Papi commits the ultimate act of Red Sox betrayal by wearing a Yankees cap. Red Sox mascot Wally the Green Monster catches him in the act. This commercial is particularly funny because everyone knows a Boston sports figure would never be caught donning the cap of the Evil Empire... Right? Right?!?

WHEN: 5/3/2007
COMPLEX SAYS: That's right, the New England Patriots star quarterback was seen in the West Village wearing the traditional Yankee fitted. Of course Boston fans were pissed and called him "Tom "Benedict" Brady, but with the help of spying on the other team Brady already brought the city three Super Bowl titles. Plus, as we found out years later, Brady sightings could always get a lot worse.

WHEN: 10/4/2007
COMPLEX SAYS: We already showed you the biggest fails of Bron Bron's career, but his first sign of disloyalty toward his home state came here during the 2007 MLB postseason. The Indians were in the playoffs for the first time in six seasons and facing the hated Yankees at home, but that didn't stop Cleveland's biggest sports star from showing his support for the Bronx Bombers. When asked about his decision James responded: "It's not fun to be questioned about it. Am I not allowed to be a fan? When I grew up watching sports, the Cowboys were a team to love; Michael Jordan was a player to love. If I say I like Michael Jordan, is that a problem because I didn't say Mark Price?" SMH, dude's been a frontrunner since day one.

WHEN: 8/7/2009
COMPLEX SAYS: Over thirty years after his heavyweight championship bout with Ken Norton in the House That Ruth Built, The Greatest visited the new Yankee Stadium for an award ceremony. Yankee captain Derek Jeter placed the cap on Ali's head, the boxing Hall of Famer then took it off, glanced at it, and repositioned it on his head. Cocked to the side, of course. Yup, Ali remains a G. No Sasha Baron Cohen.

WHEN: 11/16/2010
COMPLEX SAYS: When you're a pop star who holds weight like Justin Bieber, things like multi-platinum selling albums, a blockbuster documentary based on your life, and a song dedicated to you by BasedGod are all part of the norm. But what the Biebs reportedly did at the TD Garden last year was on a whole other level. Bieber not only gave props to Kobe Bryant for being the "greatest player on earth," but also wore a Yankees cap during his set. One of Bieber's Most Badass Sports Moments? No doubt, son.