The 25 Most Stylish Def Jam Artists

For a quarter century, Def Jam has been styling on everyone.

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Twenty-five years ago, Rick Rubin, and Russell Simmons started Def Jam Recordings in an NYU dorm room. Today the label is home to some of the most influential and stylish artists in hip-hop and R&B. Island Def Jam, Roc-A-Fella, and G.O.O.D. Music are just a few of the labels under Def Jam, responsible for hit record after hit record.

From adidas tracksuits and throwbacks, to Timberlands and tailored suits, Def Jam artists are responsible for the biggest trends and all time greatest styles. From OG’s like LL Cool J to the new generation like Frank Ocean, Def Jam is still swaggin' on everyone. This month is Def Jam’s 25 Year Anniversary and to celebrate, here is a list of The 25 Most Stylish Def Jam Artists.

Frank Ocean

25. Frank Ocean

Years on Def Jam: 2011-Present

Complex says: Frank Ocean made a big splash on the industry this year, even though he’s been working the music scene for a while. One style note about him we noticed: he must like The Karate Kid and Bruce Lee a lot because he’s always rocking a bandana and a Kung Fu silk shirt.

Juelz

24. Juelz Santana

Years on Def Jam: 2003-Present

Complex says: Like many of his fellow Diplomats, Juelz is known to have his own personal style. Starting the whole Skull Gang movement with Jim Jones, they had dudes everywhere walking around looking like a blinged out bike gang. Even Lil Wayne hopped on for a minute. And if you ever needed any Dipset related gear there was always the now defunct Santana’s Town store.

Rick Rubin

23. Rick Rubin

Years on Def Jam: 1984-1988

Complex says: The next two are not artists, but if you created one of the most influential record labels that matter, you might as well get added in there, right? At first glance you may think Rick is Hagrid from Harry Potter, but Rick Rubin has been rocking beards since it was considered cool. Peep the dope moto jacket he was rocking in the Beastie Boys video.

Russell Simmons

22. Russell Simmons

Years on Def Jam: 1984-1999

Complex says: The other half of the founding fathers of Def Jam, Russell Simmons has created a clothing empire in Phat Farm and he loves argyle patterns so much he started Argyleculture. How’s that for prep swag?

Nas

21. Nas

Years on Def Jam: 2006-Present

Complex says: If you can switch off from bubble vests and Timbs to dinner jackets and still have mad respect, it’s safe to say you got style.

Musiq

20. Musiq Soulchild

Years on Def Jam: 2000-2003

Complex says: He has the casual look down packed and the newsboy hat is a staple in his outfits.

The Dream

19. The Dream

Years on Def Jam: 2007-Present

Complex says: Like Ne-Yo he also loves his hats, specially fitteds and its rare you seem him without glasses either. If your looking for someone with a mean scarf game check out his collections.

Cam'ron

18. Cam’ron

Years on Def Jam: 2002-2004

Complex says: All pink everything—fur coats, custom paisley jackets, and a Range Rover. Nobody loved pink more that Killa Cam. If there was a point in time where you had a bubble gum pink Polo in your closet, it was probably ‘cause of this guy.

Teriyaki Boyz

17. Teriyaki Boyz

Years on Def Jam: 2005

Complex says: If you’re looking for a rap group dressed in everything Bape, look no further than the Teriyaki Boyz. They rock all the dope Bape gear everyone lines up for, and it also helps that they’re friends with Nigo.

Rick Ross

16. Rick Ross

Years on Def Jam: 2006-Present

Complex says: Rick Ross is responsible for everyone grunting all of a sudden, but let's not forget his crazy vintage shade collection.

Ne-Yo

15. Ne-Yo

Years on Def Jam: 2006-Present

Complex says: His headwear game may be a bit suspect, but Ne-yo's suit game is clean, he never misses anything even the pocket square is present.

Brandon Flowers

14. Brandon Flowers

Years on Def Jam: 2010-Present

Complex says: Hailing from the band The Killers, Brandon Flowers releases his solo debut under the Island Def Jam label. Winning awards such as “Best Dressed” (NME Awards) “Most Stylish” (NME Awards) and “Most Stylish Man” (GQ), we would like to add more, but we believe that explains it all.

The Roots

13. The Roots

Years on Def Jam: 2006-2010

Complex says: On stage rocking streetwear or dressed up in suits they’re all pretty cohesive with their style. Questlove still rocks the ‘70s style afro heavy.

fab

12. Fabolous

Years on Def Jam: 2007-Present

Complex says: Before Loso became famous as Fabolous, he called himself Fabolous Sport in part due to his affinity to Polo, and you know how those ‘Lo heads worship Ralph Lauren. Take a look at his clothing line, Rich Young, and you can see the heavy Polo references.

Big Sean

11. Big Sean

Years on Def Jam: 2011-Present

Complex Says: New on the scene, Big Sean is always seen rocking gold accessories, snapbacks, and J’s on his feet; it looks like his mentor Kanye West taught him well.

Ghostface Killah

10. Ghostface Killah

Years on Def Jam: 2004-Present

Complex says: Ghostface was always spotted rocking a robe, baroque Versace prints, and huge truck jewelry. Come on, he rocked a damn gold eagle on his arm, only he can pull that off. Can we bring the eagle back please? And how can we forget his part in making Wallabees a must-have pair of shoes?

Jay-Z

9. Jay-Z

Years on Def Jam: 1997-Present

Complex says: From his Reebok S.Dot’s to RocaWear, Jay-Z is a trendsetter. He can rock streetwear then turn around and go high-end on us. Plus, he made it cool to hop off jerseys for a second and get on that grown man swag. And if he ever name drops your brand on a song, be prepared to be flooded with orders.

Public Enemy

8. Public Enemy

Years on Def Jam: 1987-998

Complex says: If there was anyone that had a grasp on military style it was these guys—well, plus Flava Flav who had his own type of swag.

Pusha-T

7. Pusha-T

Years on Def Jam: 2011-Present

Complex says: Pusha is another artist who’s had a little Kanye style rub off on him. He has expanded his wardrobe to not only include a great streetwear collection, but also salmon colored suits and Alexander Wang blazers. His own brand, Playcloths, is killing it as well.

LL Cool J

6. LL Cool J

Years on Def Jam: 1984-Present

Complex says: One of the OG Def Jam artists kept the Kangol bucket on tight, the gold rope chains shining, and his kicks laceless. Even though he was shirtless most of the time during the ‘90s, you could always catch him with his pant leg rolled up.

Rihanna

5. Rihanna

Years on Def Jam: 2005-Present

Complex says: Rihanna can hang with the best on this list. Rocking trends like camo, military, and mod, she constantly upgrades her style and never disappoints—we think a lot of guys would agree.

Beastie Boys

4. Beastie Boys

Years on Def Jam: 1984-1987

Complex says: From hardcore punk style to track suits, gold chains, and Cazals, the Beastie Boys came on the scene with straight b-boy style. Oh, and they know a little a thing or two about kicks also—just check out their greatest footwear moments.

Big Boi

3. Big Boi

Years on Def Jam: 2010-Present

Complex says: The spotlight might be on Andre 3000 for his well-known style, but let’s not forget Big Boi has swag too. He sparked the throwback craze when he rocked a Nolan Ryan Astros Jersey in Goodie Mob’s “Black Ice” video. His Polo, Mitchell & Ness, and fur game is crazy.

Slick Rick

2. Slick Rick

Years on Def Jam: 1988-1999

Complex says: Slick Rick defined bling before there was even a word for it. He had a flamboyant style and matched everything down to his eye patch. Rumor is that the fur coat from Slick Rick’s “Teenage Love” video belonged to Rick Rubin’s grandmother, and look how well that turned out for his image.

Kanye West

1. Kanye West

Years on Def Jam: 2004-Present

Complex says: What can we say about Kanye that hasn’t been said already? From his Louis Vuitton backpacking days to his current obsession with Balmain, the man has got style down to a science. He is probably the most stylistically versatile of all Def Jam artists, plus he designed his own Nikes, Louis Vuitton sneakers, and even a high-fashion women’s line.

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