20 Clothing Items Immortalized By Rappers

Made Famous By: Slick Rick and Doug E. Fresh

Ballys haven’t had the same staying power as some other items on this list, but they were key piece of the wardrobe throughout the ‘80s and ‘90s. Two of the artists who introduced the sneakers to the mainstream were Doug E. Fresh and Slick Rick, wearing the Swiss brand on album covers in the ‘80s. Their collaborative track “La-Di-Da-Di” also featured a prominent name drop of the label when Slick Rick rapped, “Fresh dressed like a million bucks / Threw on the Bally shoes and the fly green socks."

Made Famous By: Run DMC

Before Travis Scott Air Jordans and Adidas Yeezys, there was Run-DMC’s infatuation with shell toes. The trio made the German sportswear brand’s tracksuits and Superstars (rocked without laces) their uniform, culminating with the 1986 single “My Adidas.” The result was the first major sneaker partnerships for a hip-hop act. Nowadays, that’s common, but in the ‘80s, it was monumental. Decades later, there are few associations stronger than Run-DMC and Adidas.

Made Famous By: EPMD and Cypress Hill

Erick Sermon and Parrish Smith helped transition the chill headwear option from the lake to the streets of Brentwood. Throughout the ‘80s and ‘90s, the duo wore them on stage, in photoshoots, and on album art (see Unfinished Business, in 1989). We also have to give a nod to Cypress Hill, who also donned the headwear. Rappers like Schoolboy Q (more on that later) also kept bucket hats in rotation years later.

Made Famous By: LL Cool J

Kangol was founded in the United Kingdom in the 1930s, but thanks to LL Cool J many people associate the Kangaroo-stamped hats with New York City street style in the ‘80s and ‘90s. You would have been hard pressed to spot LL without a fuzzy Furgora on his head at the time.

Made Famous By: Eazy-E

When you picture Eazy-E, you picture Locs. The generic-looking shades are actually a style by Giorgio Armani. As vintage eyewear dealer Julian Emani told Complex in 2020, they’re “super rare and very much a vintage collector's item, especially when it comes to finding the exact model that he wore.” In his day, Eazy had jokes for anyone asking about them.

Made Famous By: N.W.A.

If Jay-Z made the Yankees hat more famous than any player could, N.W.A. deserves their flowers for making silver and black gear more famous than Howie Long or Marcus Allen. From snapback caps to satin jackets, the Los Angeles Raiders gear became a staple for Ice Cube, Eazy-E, Dr. Dre, MC Ren and DJ Yella. The placement helped turned the Raiders into more than a city’s favorite football team—it became a globally recognized brand.

Made Famous By: Raekwon

Perhaps the most revisited example of a rapper co-sign in fashion history, Raekwon’s fit in the “Can It All Be So Simple” video is the stuff of legend. Over 30 years after its release, people are still talking about the “Snow Beach” anorak from Polo Ralph Lauren. It’s onsidered one of the most coveted Polo pieces of all time. Polo re-released the item for the first time in 2018 to celebrate its 25th anniversary. Originals from 1992 still fetch thousands.

Made Famous By: Snoop Dogg

Snoop Dogg wasn’t exactly known for keeping Tommy Hilfiger in rotation in the ‘90s, but the brand is connected to one of his most memorable style moments. To promote his debut album Doggystyle in 1994, Snoop took the Saturday Night Live stage in a colorblocked navy blue, red, and white rugby sweater with “TOMMY” written in block letters across the chest. Sales immediately boomed. Within days, the style had sold out.

“Snoop wearing this Tommy Hilfiger Rugby was the most impactful marketing moment of my young life,” Kanye West wrote in an Instagram post back in 2022.

Tommy Hilfiger as a whole was cemented as a part of the hip-hop uniform throughout the ‘90s, thanks to various artists, but few pieces hold as much weight as Snoop’s rugby from ‘94. It even saw a re-release in 2024 to celebrate the anniversary of its release.

Made Famous By: Ghostface Killah

Wallabees were already popular throughout New York City, especially withing the Jamaican community, by the time Ghostface rapped about them. But the Wu-Tang member’s interest in customization (see the classic skit on Cuban Linx) and general level of enthusiasm for the sneakers made them iconic around the world. Son, I had crazy visions…

Made Famous By: The Notorious B.I.G.

Biggie in a rainbow Coogi sweater. It’s an image that has been referenced and repurposed countless times. When fans try to recreate classic Biggie looks, the Coogi sweater is usually the go-to. Even the Brooklyn Nets unveiled jerseys inspired by the Brooklyn rapper, featuring colorful, Coogi-esque panels. Mainstream culture has absorbed Big thoroughly—surely you’ve been in a Manhattan restaurant that’s played his music, or featured a line of his as part of the decor. But that doesn’t make Biggie any less cool.

Made Famous By: 50 Cent

Not every piece of clothing propelled by a rapper is a flattering one. One such example: the square-neck tank top that 50 Cent kept on his body during his meteoric rise in the 2000s. These became inescapable for a little bit, as many kids and adults were eager to emulate the hottest rapper on the planet. But real heads will never forget that Cam’ron called them “brassiere tops.”

Made Famous By: Jay-Z

Like we said, not every notable rapper fashion trend ages so gracefully. Perhaps the best example of this is Jay-Z’s button-up shirt era. Coming off his era of throwback jerseys, Jay-Z rapped, “And I don't wear jerseys, I'm 30-plus / Give me a crisp pair of jeans, button-ups,” on 2003’s “What More Can I Say.” The moment triggered a movement of business casual club attire that many millennials try to forget.

Made Famous By: Lil Wayne

Weezy F. Baby wasn’t the rapper who put BAPE on the map in the states. That distinction belongs to Pharrell. But Lil Wayne did eventually adopt NIGO’s brand and its loud camo pieces (sparking one of the most storied beefs in rap history?). The greatest example of Lil Wayne’s BAPE era came at the 2005 BET Awards. Some people simply refer to the purple camo hoodie as “the Lil Wayne hoodie.” In recent years, Playboi Carti added to the lore of the item when he referenced it for his YVL x Bape collab.

Made Famous By: Juicy J

A black T-shirt covered in glow-in-the-dark green skulls sounds more like something you would see on the wall at Hot Topic than an iconic piece of hip-hop fashion. Then, Three 6 Mafia’s “Stay Fly” video dropped in 2005 and everything changed. Juicy J popped on screen rocking the skull-covered tee, from Liquid Blue, a company primarily known for its tie-dyed Grateful Dead tees. The garment has become such a piece of hip-hop lore that Supreme revived the print in 2018. The loud graphic has also been rocked by rappers like Travis Scott, Juice WRLD, and Playboi Carti.

Made Famous By: Big Sean

The design that helped Yoon Ahn and Verbal’s Ambush take off was worn by various stylish celebrities, from Kanye West to Rihanna. But Big Sean owned the trend. At the time, the Detroit rapper was still bubbling, making waves for his connection to G.O.O.D. Music and Finally Famous mixtape series. He wore the POW! chains in every color, usually many at a time.

Made Famous By: Tyler, the Creator

Tyler, the Creator didn’t put Supreme on the map, but he definitely helped an entire generation of kids fall in love with the brand. A big reason for that was the camp caps that donned his head during his Odd Future days when he first burst onto the scene with “Yonkers” in 2011. The olive green cap with the leopard print brim that he wore to accept his “Best New Artist” award at the 2011 MTV VMAs is still connected to him to this day.

“That was the moment where people really found out what Supreme was, at least on a mainstream level,” RIF LA co-owner Jeffrey Malbanan told Complex in 2024.

Made Famous By: Kanye West

Ye has made plenty of clothing items famous. Frankly, he could have a list dedicated to himself. For the sake of this exercise, we are going to focus on only one of them: the Givenchy Rottweiler T-shirt. Ye was first photographed in the design in March 2011, three months before it came out. Rihanna rocked it and it was bootlegged by designers like Heron Preston. The ferocious imagery that defined Riccardo Tisci’s time at Givenchy informed the art direction for Watch The Throne (Tisci designed the album cover and select merch).

“He wore the T-shirt, and the T-shirts flew out. They were gone. For me, it one of the first times I was like, ‘Man, this is a direct correlation from his influence to people,’” former buyer for Barneys and Bergdorf Goodman, Julien Decanali, told Complex back in 2022.

Made Famous By: ASAP Rocky

Pretty Flacko is another rapper who can be credited with making a handful of clothing items famous. He helped put on (and kill) Benn Trill and Hood By Air, and he introduced a new generation to Raf Simons. But in 2017, a partnership with Guess Jeans revived the brand’s striped T-shirt. The archival design from the ‘90s came back in a variety of flavors, and the trend burned bright and fast before fading away a few years later. But if you were a certain age in 2017, you remember these being everywhere, and it was all because of Rocky’s important co-sign.

Made Famous By: Schoolboy Q

Like Guess T-shirts, this one will resonate with a certain age range. If you were in high school or college in the 2010s, you remember the bucket hat resurgence. Schoolboy Q made the accessory (and his circular shades) his go-to uniform. Milkcrate Athletics versions covered in colorful patterns were the creme de la creme, but any bucket hat would suffice. He’s even rocking a bucket hat on the cover of his debut album Oxymoron.

Made Famous By: Chief Keef

You know the photo. A 16-year-old Chief Keef poses in a Chicago bathroom. Gucci ski goggles. Damier-print Louis Vuitton belt. But the real star of the fit is the “Lead Never Follow” baseball shirt, which came from LDRS 1354, a historic sneaker and streetwear boutique in Chicago. It has become a defining piece of Chief Keef’s legendary career and streetwear history. To this day, you can buy bootleg versions on sites like Etsy that bill them as the “Chief Keef Lead Never Follow” shirt. We also just saw Molly Santana recreate the legendary fit for Halloween.