The 25 Most Iconic Fashion Pieces in Sports History

Sports is all about the W. Win close, win ugly, whatever, just win. But there's a special place in sporting lore for winning with style—many of the greatest athletes, coaches, and reporters have remained cultural icons thanks to the fashion choices that they've made. Athletics can be as much a stage for chambray, fur, and houndstooth as they are for blood, sweat, and tears. And while we're not going to suggest that the pieces outduel the performance, they can take on a status of their own. From a wrestling mask with a 50-year career, to the fedora behind America's team, to a quintet of baggy shorts that scared America in the '90s, these are the 25 most iconic fashion pieces in sports history.

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Debuted: 2001
Famed Appearance: Patrolling left field for the Red Sox

The ethos, “Manny being Manny” certainly spilled over into the fashion world for the Dominican slugger. Working from the top down, Manny's do-rag became synonymous with his dreadlocks, something that would get him in hot water with Joe Torre in L.A. And from the bottom, Manny was known for sporting baseball pants that looked more suited for an MC Hammer video. If skinny jeans are any indication as for what's to come for baseball uniforms, Ramirez got out just in time.

Debuted: 1970
Famed Appearance: In the crease for the Boston Bruins in 1970

It's commonplace nowadays for professional net-minders to man the crease behind an intimidating goalie mask. They have former Boston Bruins goalie Gerry Cheever to thank for this practice. Always the type of player to skip out of practice in favor of a smoke and a drink, Cheever did just that after taking a puck to the face during a training session. Following a tongue-lashing by his coach, Harry Sinden, the always cheeky Cheever had the equipment manager place a scar on his mask, and would add a fresh scratch every time he was struck with a ruthless slapper.

Debuted: 1972
Famed Appearance: On the sidelines, in the dugout and on the court

The venerable reporter's style is reminiscent more of New Jack City's Nino Brown, than that of a trusted source of information on professional ball courts across the country. Sager has been in the business since 1972, and a keen eye will catch a glimpse of him waiting to greet Hank Aaron at the plate after breaking the Babe's record. With an estimated 118 different suits to choose from in a cacophony of colors, and amply prepared to be paired with a pair of ostrich or stingray loafers, his suits truly are a cultural phenomenon.

Debuted: 1991
Famed Appearance: On the Hazeltine National Golf Course in 1991

Payne Stewart's untimely death not only deprived sports fans of one of the more skilled and personable players on the tour, but it also ended an entertaining run of golf ensembles that Stewart would wear at various tournaments across the United States. One of his most memorable was the navy blue and orange striped get-up, paired with his signature cap, which he wore when we took home the top prize at the 1991 U.S. Open. A little silly looking? Of course. Golf could use a few doses of silly though, word to Billy Madison.

Debuted: 2006
Famed Appearance: In the BCS National Championship Game versus Oklahoma

The Tim Tebow phenomenon is a sports conundrum that rivals that of the decision of King Solomon. In a similar biblical framework, the passages that Tebow wore under his eyes during his time at the University of Florida only made his mythical status that much greater. Taking the field during the 2008 BCS National Championship Game with the inscription “John 3:16” under his eyes, this biblical homage would make it the most searched item on Google at the time.

Debuted: 1932
Famed Appearance: In the ring, versus Black Shadow

Rodolfo Huerta, better known by his wrestling alter ego El Santo, was one of the greatest legends in Mexican sports, appearing behind his signature mask in mediums including matches, comic books and cinema. In a bizarre twist of fate, El Santo would die in 1984, just a week after removing his mask and showing his face to the public for the very first time.

Debuted: 1901
Famed Appearance: In the Philadelphia Athletics dugout

In today's age, managers are obligated to wear a baseball uniform if they are going to observe the game from the dugout. Conversely, in the glory days of baseball, Connie Mack would park himself in the dugout as manager of the Philadelphia Athletics sporting fashionable duds that included tailored suits and matching hats. Legend has it that the only time his players saw him out of “uniform,” was during a 90 degree day in St. Louis where he loosened his tie a bit.

Debuted: 1974
Famed Appearance: Grand Slam Finals versus John McEnroe

Both Bjorn Borg and John McEnroe had a way with style, seemingly embodying everything that made the 1980's a curious fashion era. When the two met in the 1980 U.S. Open Final, Borg sported his classic Fila Headband, which corralled his locks that seemed to go on for days. While he'd go on to lose the match, he'd prove to win the fashion war against his nemesis. His athletic silhouette will certainly be one we won't soon forget.

Debuted: 1981
Famed Appearance: In the Ring for Wrestlemania III versus Andre the Giant

There are only a handful of athletes who have maintained a certain look in both their professional and personal life; Hulk Hogan is one of those people. The Hulkster wore several iconic pieces over the years, from his bandana to boa, but it's surely his classic yellow tanktop that rises and rips over the rest. This signature piece was draped over Hulk's beefy frame as he paraded down the Silverdome walkway for Wrestlemania III in front of 93,000 screaming fans in route to one of the most iconic matches in wrestling history.

Debuted: 1992
Famed Appearance: On the pitch for Manchester United

The French international footballer certainly had a flare for the dramatics, whether that was scoring dazzling goals at Old Trafford, or karate kicking Crystal Palace fans. But it was perhaps his flipped collar on his Manchester United kit that will forever keep him cemented in football lore.

Debuted: 1966
Famed Appearance: On the court for the LSU Tigers

Everyone described pistol Pete Maravich the same way, from his coaches, to gawking fans in the stands: “that skinny guy with the mop top and floppy gray socks can play ball!” There's even a children's book you can purchase called Floppy Socks and Moppy Hair. Never in the history of sports has the lack of elasticity elicited such a lasting memory.

Debuted: 1986
Famed Appearance: On the field for the Chicago Bears in 1986

For those of you unfamiliar, “he's the punky QB known as McMahon, when he hits the turf he has no plan.” Jim McMahon exuded style on and off the field, but his lasting memory will be the headband he wore with the name “Rozelle” scrawled across it, a not so subtle jab at the commissioner at the time, who had fined McMahon previously for having a corporate sponsorship (adidas) on a previous piece of headwear. Bear down.

Debuted: 1971
Famed Appearance: On the sidelines, notably for Army and the Indiana Hoosiers

The General went into battle sans suit and tie like other college coaches in favor of a more understated and “ornery grandfather” look thanks to his vast sweater collection. Even as he's segued into a broadcasting career, where his peers once again dressed in a more formal fashion, the sweaters have remained for Coach K's mentor.

Debuted: 1960
Famed Appearance: On the Dallas Cowboys sideline

America's team had someone at the helm who certainly looked the part of world leader. With his trusty Stetson Fedora on his head, Tom Landry lead the Dallas Cowboys to two Super Bowl victories and five NFC titles. His coaching methods were steeped in tradition; his Stetson Fedora was legendary.

Debuted: 1975
Famed Appearance: On the court, for the Los Angeles Lakers

It wasn't until Kareem Abdul Jabbar headed west that his signature goggles would make an appearance. While wearing them he'd win his fifth and sixth MVP awards and break Wilt Chamberlain's record for career points, all the while looking like he was dabbling in some activities that would make Walter White proud.

Debuted: 1973
Famed Appearance: On the court in Madison Square Garden

Walt “Clyde” Frazier was one of the first NBA players to have a signature shoe, where as in today's (locked out) game, it seems as if any and every player who gets more than fifteen minutes of floor time gets his name on a sneaker. The Puma Clyde, unveiled in 1973, is now in its 4th decade of production, cementing it as one of the most iconic basketball shoes of all-time.

Debuted: 1960
Famed Appearance: In the ring, for a rematch versus Sonny Liston in 1964

Ali vs. Liston II was billed as the fight of the century. After a questionable ending to their first bout, and a six month layoff for Ali due to injury, many wondered if he'd sting more like citrus in a cut than like a bee. That would be answered quickly after Ali had put Liston on the canvas with what some would call a “phantom punch.” As Ali stood over his fallen opponent, photographer Neil Leifer, would snap one of, if not the most iconic sports images of all time. While they were just run of the mill trunks, they happened to be worn by the baddest man on the planet.

Debuted: 2000
Famed Appearance: On the sidelines for the New England Patriots in Super Bowls XXVI, XXVIII, XXXIX

Bill Belichick's outward appearance resembles that of a telemarketer with sloth-like tendencies. Every Sunday he roams the Patriots sideline with his headset guarded by a drab hood, the sleeves long since abandoned on the sweatshirt like they were the tags. This look may scream, “bum,” but he's got the rings to prove that his style of dress in Lombardi Trophy-chic.

Debuted: 1985
Famed Appearance: Versus Michael Spinks for the heavyweight championship of the world

It's what Iron Mike Tyson chose not to wear during his Heavyweight Championship bout with Michael Spinks that is truly startling. Tyson emerged from the dressing room in the Trump Plaza in Atlantic City wearing his signature black trunks, but with no top. No towel. Nothing. He even chose to enter with nothing but ominous sounds of chains hitting concrete in lieu of traditional entrance music. Tyson looked like he was there to fight…and he did for 91 seconds before knocking Spinks out.

Debuted: 1971
Famed Appearance: On the New York Jets sidelines, injured in 1971

Broadway Joe was truly a fashion pioneer at a time when people looked to Bart Starr and said, “that's what a quarterback looks like.” Namath was flamboyant and understood that playing to New York fans was exactly like being a Broadway actor. Rather than wear conventional and bulky team jackets on the sideline, Joe Namath instead took his fashion cues from the likes of Frank Lucas and Nicky Barnes and went with a full-length fur.

Debuted: 1986
Famed Appearance: On the field, notably for the Atlanta Falcons, San Francisco 49ers and Dallas Cowboys

With a nickname like “Prime Time,” there's absolutely no way you can get away with looking like a one-bar facemask-sporting kicker on the field. Forgoing the dookie-gold ropes he wore while playing baseball, Sanders wore that do-rag like it was every bit as important as his helmet, or dancing after a spectacular return. How important was it to Prime Time? He placed a do-rag on his bust after being elected to the Hall of Fame in Canton.

Debuted: 1982
Famed Appearance: On the Chicago Bears' sideline, Super Bowl XX

In the city of Chicago, the social hierarchy revolves around football and food, falling in this exact pecking order: Ditka, beer, deep dish, Ditka. While the Miami Dolphins have been lauded for their perfection back in 1972, it was the 1985 Chicago Bears who were undoubtedly the most dominant football team of all time after running through the playoffs with a 91-10 point differential. Ditka's block letter sweater vest was the filet-mignon of athletic fashion because it conveyed the perfect amount of elitism. It said, “We're good, and we know it.”

Debuted: 1991
Famed Appearance: On the court, 1991-92 & 1992-93

It's been twenty years since Chris Webber, Jalen Rose, Juwan Howard, Ray King, and Jimmy Jackson abused teams in Ann Arbor, but their impact on basketball style remains. Michael Jordan was the first to rock long shorts, but it was the Fab Five that took the look to the knee and beyond. Along with their black socks and take no shorts attitude, the Fab Five ushered in a brash new era in basketball.

Debuted: 1954
Famed Appearance: On the Alabama Crimson Tide sidelines, 1958-1982

In his tenure at Alabama, Bear Bryant won six national titles and thirteen SEC championships. Almost as iconic as the number-clad helmets worn by the Crimson Tide players was another signature piece of headwear sported by Bryant. His stylish houndstooth hat was certainly every bit as famous as logos of that era like Ford and Lucky Strike. Bryant earned his nickname for fighting a bear. Who would have thought that decades later the fedora would be championed by guys who look like one?

Debuted: 1988
Famed Appearance: 1988 Slam Dunk Competition

Tinker Hatfield, a former architect, took over Air Jordan design duties in both a nuanced and grand fashion. Working closely with His-Airness, the III's were not only the first shoe to represent an athlete's personality, but were also the first appearance of the now iconic Jumpman emblem. That year saw Jordan soaring from the free throw line to a Slam Dunk title that in them, as well as finishing the regular season averaging 35 points, topping the 40 point mark a stunning 18 times. It's gotta be the shoes, right?