The 12 Most Stylish New York Yankees of All Time

The Yankees are infamous for numerous reasons. Depending on who you ask, they're either the most beloved or the most hated team in all of sports. They're certainly the most decorated franchise, and, if you take a look at their complete history, they are by far the most stylish baseball team ever.

Baseball players aren't really known for their style off the field, but the Yankees are the rare exception. Playing in the fashion capital of America definitely has something to do with it, and being in the country's harshest media spotlight means you have to be on point on the diamond and keep it steezy away from the ballpark. From the legends of the game to fan favorites, these are The 12 Most Stylish New York Yankees of All Time.

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Years as a Yankee: 1995 - Present
Yankee Highlights: Five World Series Championships; Rookie of the Year; New York Yankees Career Hits Record

We've lauded Jeter's style when he was a young go-hard, but he definitely fell into the black hole of style that existed from 2001-2009 or so. Lucky for us (actually, maybe not, since it means he'll be catching even more NYC va' than he was before) Jeter's stepped away from the dark side and gotten with the sartorial times.

Jeter's reined in the monstrously baggy gear and boxy suits for clothes that actually fit. Whether it's suits in unique colors but classic fit, or casual gear that doesn't billow in the wind, Jeter's style has found its stride. Because when you're the face of the team that everyone else in the country loves to hate, you better look sharp. Even if that face has biblically known some of the most beautiful women out there.

Years as a Yankee: 1950-1957 (Player); 1975-1978, 1979, 1083, 1985, 1988 (Manager)
Yankee Highlights: Four World Series Champsionships as a player; One World Series Championship as manager.

Billy Martin's time as a manager of the Yankees was bumpy as hell, but his style was consistently smooth. As George Steinbrenner's simultaneous confidante and nemesis, Martin served as the Yankee manager five times, and was a stylish presence in the NY papers throughout his constant firing and re-hirings.

In a famous beer commercial filmed alongside Steinbrenner, Martin rocks a colorful plaid blazer with his shirt collar over the jacket lapels, and perfected the old man at the ballpark look when he watched games from the stands. And his most famous move was fucking up the kick game of umps who had blown a call by kicking dirt onto their feet. Cold move, Billy.

Years as a Yankee: 1949-1960 (Manager)
Yankee Highlights: Managed seven World Series Champion teams.

Casey Stengel was one of baseball's most eccentric characters, and he infused his famous kookiness into his suit game. Peep the paper baseball transformed into a pocket square! His signature funky ties were as well-known as his unique strategies that brought him seven World Series titles with the Yankees. "The Old Perfessor" was one of the rare Yankee managers who was loved by the Yankee faithful well after he stepped away from the field, and he never failed to show up without a crispy get-up that had at least a few personal twists thrown in.

Years as a Yankee: 1977-1981
Yankee Highlights: Two World Series Championships; 1977 World Series MVP; Hit three home runs in Game 6 of the 1977 World Series.

Reggie Jackson may have had some of the most clutch postseason performances of all-time, but his style came through year-round. His funky fresh steez fit perfectly in with the most stylish dudes of the times, and he rocked some of the dopest on-field glasses baseball has ever seen. He may have had a rocky relationship with manager Billy Martin, but no matter what problems Martin had with Jackson's performance on the field, no one could argue against the fact that Mr. October was keeping it one hunna off the diamond.

Years as a Yankee: 1985-1989
Yankee Highlights: Four time AL Stolen Base Champion

If you were able to spot the speedy Henderson between him stealing bases, then you'd definitely recognize his status as one steezy dude. His immaculately coiffed jheri curl stayed intact even when he was sprinting 90 feet at a time, and his appearances off the field cemented his place on this list. Perfectly placed collar pins showcased his devotion to the classic sartorial game, while gold accessories and dope sunglasses on the diamond proved he was a modern day style icon of his contemporaries.

Years as a Yankee: 1969-1979
Yankee Highlights: Captain of two World Series Champion teams; 1976 AL MVP; Seven time All-Star.

Thurman Munson is usually thought of as the No. 1 fan favorite Bronx Bomber of all-time. He was considered the heart and soul of the 1970s era Yankees, and led the team to two World Series rings. Away from the catcher's box, Munson was also a leader in style. His lapels and collars were as enormous as his leadership, and were almost enough to distract away from his droopy moustache.

Combining plaid and polka dots takes the cajones that are also required to lead a team that's racked by the public feuding of manager Billy Martin and owner George Steinbrenner. But Munson of course pulls it off, as he does with a flippantly tousled collar under his uniform—a feat not pulled off since 1979.

Years as a Yankee: 1936-1942, 1946-1951
Yankee Highlights: Nine World Series Championships; Three AL MVP awards; Record 56 game hitting streak.

His incredible 56-game hit streak and stellar 13-year career with the Yankees aside, Joe DiMaggio is probably best known to non-baseball fans for his brief marriage to Marilyn Monroe. And you don't land the biggest sex symbol of the 20th century without having on-point style. The "Yankee Clipper" was widely considered by his peers to be one of the classiest guys in the game, and the same could be said of his '50s-era steez.

"Joltin' Joe" was done up to the nines when he went out on the town with his boo, and still kept it classy when dressed down at home. And unlike a lot of athletes that may let themselves go after they step out of the spotlight, DiMaggio kept up his appearances and very advanced levels of formalwear as he aged gracefully into legend status.

Years as a Yankee: 1973-2010 (Owner)
Yankee Highlights: Oversaw seven World Championship teams.

Before Rick Ross made the claim, there were two men in America simply known as The Boss. One was a singer from Jersey, and the other was George Steinbrenner. Widely considered one of the most divisive figures in New York and in baseball, Steinbrenner garnered hatred and love from his players, his coaches, and from the Yankee faithful. But what couldn't be argued was the fact that the man had style.

Steinbrenner owned the Yankees from 1973 until his death in 2010, and was one of the most visible examples in America of what true bawse style looked like. With classic WASP style that meant flared plaid pants in the '70s, navy sportcoats over french cuff shirts, and everything in between, Steinbrenner ruled the Yanks with an iron fist.

The Yankees may have had some record breaking payrolls, but Steinbrenner was the man signing checks and dressed like the man in charge. Of course, the only accessories that ever truly mattered to The Boss were his World Series rings, and he wore them proudly.

Years as a Yankee: 1976, 1979-1984
Yankee Highlights: Batted .358 in 1979

Even if you were sitting in the last row of the upper deck, you knew where Oscar Gamble was on the field at all times. His glorious afro earned him the honor of Phil Rizzuto personally dubbing him "The Big O," and he was a perennial favorite of the hometown faithful. While many players wilt under the intense spotlight of the New York media, Gamble thrived on it. Sportswriters loved him, and his personal style was on par with the other groovy cats that dominated NYC in the '70s. While it's not an official honor, Gamble will forever be remembered as having the Yankee with the best haircut of all time.

Years as a Yankee: 1962-1969
Yankee Highlights: Three time All-Star.

Joe Pepitone was a fan favorite throughout his tenure with the Yankees. His memorable home runs were certainly a significant factor in this perception, but the country's most stylish city will always embrace and claim a stylish dude as their own. Pepitone's part-groovy, part-classic steez could've fit in with any Martin Scorsese flick focusing on NYC in the late '60s and '70s. Pepitone continued to be involved with the Yankees organization well after he retired, and kept his style on point at every appearance.

Years as a Yankee: 1989-1990
Yankee Highlights: N/A

He was only a Yankee for two seasons, but Deion Sanders definitely brought the flash and swagger he was famous for to the Bronx. When he wasn't streaking across the Yankee Stadium outfield in 1989 and 1990, "Primetime" was weighing down his neck and wrists with massive amounts of gold set against a backdrop of all leather everything.

He eventually was traded to the Braves, which made sense for him focusing on his football career with the Atlanta Falcons, but Sanders was ostensibly the most stylish athlete in NYC at the dawn of the '90s. And probably the most badass. Before his first at-bat as a rookie, "Neon Deion" drew a dollar sign in dirt of the batter's box. He then proceeded to pop up and didn't run to first base, eliciting boos from the home crowd. Whatever, the important thing is that, for two years, the Bronx was home to the most stylish athlete of the '90s.

Years as a Yankee: 1920-1934
Yankee Highlights: Seven World Series Championships; 1923 AL MVP; 12 AL Home Run Championships

Babe Ruth was hands down the first superstar in sports. It's pretty difficult to find any off-field photos of baseball players from this era, but the Babe is the sole exception. His exploits away from the diamond were as celebrated as his heroics at the plate, and this included his flamboyant and luxurious sense of fashion.

His bold, brash clothes were part of his magnetic personality. Ruth started from the bottom and was crowned king of the sport, so of course he had to dress in the finest regalia of furs, silks, and bespoke suits. No other type of wardrobe would do for a man who ruled NYC and held court in "The House That Ruth Built." Many of his records have since fallen, but his status as American icon and the most stylish Yankee of all time haven't even come close to being eclipsed.