For Pharrell it’s equal parts cool, casual, and refined. The musican/producer is no stranger to the luxury fashion market, but he never looks better than with a polo—opting to elevate the casual garb with his sophisticated sense of styling. —Kyle Rice
Musician/Producer Pharrell Williams gets inked by Mister Cartoon Downtown Los Angeles 1998.
There isn’t an artist alive more connected with the polo tee than Kanye West, pictured here in 2004. Since his College Dropout days, the artists has been repping the brand both on his back and in his music. “I’m doing pretty good as far as geniuses go. And I’m doing pretty hood in my pink polo,” he raps on “Barry Bonds,” a testament to his love for the brand despite the ney-sayers. —KR
While performing live, guitarist and founding member of the Grateful Dead, Bob Weir, often paired his famous cut-off denim shorts with a pink or purple polo tee shirt. When asked about his sartorial choice he recalled, “When we would be on the road and wanted to go to a nice restaurant, you’d need to have a shirt with a collar, and the polo did the trick.” The purple polo tee will live on in pop-culture history forever, worn both by Weir and his skeletal puppet in the Dead’s first music video ever for their 1987 single “Touch of Grey.” —Alison Weinflash
Bob Weir shot by the legendary rock photographer Richard E. Aaron.
Ciara and polo go back. Remember the time she ditched her boyfriend Russell Wilson to hang with the Ralph Lauren models? Or how about kicking off fashion week with coffee at Lauren’s shop in New York? The singer is never too far from the brand, but why would you be when you look as good as she does in her polo shirt? —KR
Model Bridget Malcolm, singer Ciara, and model Samantha Gradoville attend Polo Ralph Lauren For Women during Mercedes-Benz Fashion Week Spring 2015 at Cherry Hill in Central Park
An artist accustomed to the everyday polo, this 2005 MTV Video Music Awards rehearsal look is a surprising change from Jamie Foxx’s usual colorful polo picks. Just like his large body of work in the entertainment industry, Foxx’s love for every bit of the polo color spectrum is far-reaching. This simple look just goes to show that colorful polo or not, Jamie Foxx looks good in a polo on any day! —Uvie Bikomo
Jamie Foxx during 2005 MTV Video Music Awards – Rehearsals – Day 1 at American Airlines Arena in Miami, Florida, United States. (Photo by KMazur/WireImage)
Fat Joe has become so synonymous with the polo shirt we can’t picture him in anything else. From the release of his 2002 album Loyalty to his more recent outings standing shoulder-to-shoulder with Diddy, Jennifer Hudson, and Mary J. Blige, the polo has become a signature and influenced his style for the long haul. —KR
Rapper Fat Joe during “The Sopranos” On Location in New York City – Aug. 21, 2006 at St Rita’s Church in Queens
Diddy. Puffy. Sean. Love. Whatever you prefer to call the man, it is undeniable he has swagger. And what better way to build his style than with the polo tee. Whether it’s layered under a Sean John bomber, or rocking it on its own, Diddy in a polo will always look undeniably cool. —KR
Sean ‘Diddy’ Combs arrives at the Palms Pool & Bungalows at The Palms Casino Resort on Sept. 4, 2011 in Las Vegas
An elevated sense of dapper sophistication is the only way to describe Tariq Trotter’s fashion. Though his days rocking the polo tee solo may be long behind him, he’s found ways of incorporating it into his everlasting swag. It’s safe to say the man knows style. —KR
Tariq ”Black Thought” Trotter of the Roots performs at the 3rd Annual Roots Picnic at the Festival Pier on June 5, 2010 in Philadelphia
Did OutKast invent the brand collab? Perhaps. As the group got bigger, their dapper Atlanta style influenced many, including the wearing of the polo tee as it became staple in their look. The hit single ‘Hey Ya!,’ adorned with Polo logos in every corner was practically a Ralph Lauren ad that solidified their love of the brand to audiences around the world. —KR
Big Boi and Andre 3000 of OutKast during 2004 MTV Video Music Award in Miami
Whether it’s his attendance of parties or an interview with MSNBC, Trey Songz, pictured here in 2012, is almost always rocking a polo shirt. At one point there was talk about Songz launching his own line of polo-like shirts featuring his track titles like “LOL :-)” and “Yuup!” —Carys Douglas
Trey Songz Visits the Young Hollywood Studio on August 8, 2012 in Los Angeles, California. (Photo by Mary Clavering/Young Hollywood/Getty Images)
Not the originators of the movement, but when it comes to redefining who the polo was made for, Boyz II Men are definitely one of the earliest examples. Since the 1990s, the quartet, now a trio, were synonymous with the style and energy of the Lo-Lifes movement and polo. —KR
Boyz II Men attends the Second Annual VH1 Honors on June 22, 1995 in Los Angeles
Juvenile might be a bit of an underdog when it comes to styling a polo. Whether it’s fitted under an oversized FUBU jacket, accessorized with a pair of Dolce & Gabbana glasses, or worn on its own, Juvenile understands that a good basic is all you need to have a great sense of fashion. —KR
NEW YORK, NY – AUGUST 14: Rapper Juvenile attends the Juvenile Mix Tape 1istening session at The Source Magazine on August 14, 2012 in New York City. (Photo by Charles Norfleet/Getty Images)
One half of the southern-rap duo, MJG has been wearing Polo for years. In fact he makes the notion quite apparent, rapping about the craze feeling irrelevant after the masses jumped on the trend. “Polo polo polo I been doin’ that for years,” he states on the single ‘Bring It Back.’ —KR
MJG performing during VERZUZ Bone Thugs-N-Harmony and Three 6 Mafia at Hollywood Palladium in 2021
Despite the rumors that are constantly circling the Atlanta rapper, there is one that is absolutely true — T.I. knows how to style a polo. In his infamous single to date ‘Whatever You Like’ he can be found wearing a polo as he raps in front of two of his many lux cars. What better way to accesorise your tee than with a Rolls Royce? —KR
T.I. performing at a One Night Only show for AXE Music at Capitale on Aug. 16, 2010 in New York