The 10 most memorable hip-hop fashion looks of all time

The relationship between hip-hop and fashion has evolved over the decades. What was once seen as a niche way of dressing slowly transitioned into being the standard of inspiration when it began to grace runways, starting in the 1980s and continuing on to present day. Author and journalist Sowmya Krishnamurthy explores the history of this relationship in her definitive new book, Fashion Killa: How Hip-Hop Revolutionized High Fashion (Gallery Books).

In Fashion Killa, Krishnamurthy looks back at some of the most impactful collisions between hip-hop and fashion—think the industry’s captivation with Lil’ Kim or Tommy Hilfiger’s embrace of rap and hip-hop in his ad campaigns. Music and fashion titans such as Diddy, Kimora Lee Simmons, Dapper Dan, and the late Virgil Abloh all receive their well-deserved flowers in the new read as well.

Krishnamurthy wanted Fashion Killa to be a definitive look back at how hip-hop shaped the larger culture, but especially at its influence over how we dress on a daily basis. Below, the author looks back at 10 of the most memorable looks from the heyday of hip-hop and why we still can’t stop thinking about them today.

Chanel 1991 runway show

Karl Lagerfeld pulled from hip-hop and street style when he dreamed up Chanel’s iconic 1991 runway show, featuring a dizzying array of gold chains, nameplates, and baseball caps. I can only imagine what was on his playlist at the time!

Tupac in Karl Kani

Tupac Shakur not only modelled for Karl Kani but was also the creative director of this shoot. One of my favourite interviews in the book is how Karl Kani described working with the revolutionary rapper: I was like, ‘Yo! Pac. How much would you charge to do an ad?’” The rapper got quiet. “He looks at me and says, ‘Yo. You’re Black. I don’t charge my people for nothing.’

Aaliyah in Tommy Hilfiger

Aaliyah epitomises sexy cool and I’ve been forever obsessed with her in Tommy Hilfiger. As the designer told me, “Aaliyah had this amazing, laid-back aura—she was effortlessly stylish, and she just radiated relaxed confidence. You couldn’t help but be drawn to her.” Absolutely.

Mary J Blige and Lil’ Kim

What’s left to say about Lil’ Kim’s iconic MTV Video Music Awards look that hasn’t been said? The left breast that changed fashion forever.

Jennifer Lopez and Puff Daddy

The NSFW dress that literally launched Google Images. That was “breaking the internet” before the term existed. It doesn’t matter how many times I see Jennifer Lopez in her famous Versace dress. It still makes my jaw drop.

Dame, Posh Spice, and Biggs

This photo of Damon Dash, Victoria Beckham, and Kareem “Biggs” Burke captures everything I love about hip-hop fashion in the ’00s. The extra-big white T-shirts, Air Force 1s, and two-way pagers. A lot of people don’t remember when Posh was down with Roc-A-Fella Records—but there’s pictures to prove it!

Tupac in Milan

One of my absolute favourite photos in Fashion Killa is of Tupac Shakur in Milan. It was shot by David McLean—who was so kind to contribute it for the book—and captures the rapper in a rare quiet moment that truly showcases his beauty and essence.

Cardi B, 2018 Met Gala

Cardi B really took the Met Gala theme of “Heavenly Bodies” in 2018 seriously. I love how regal and sexy she looked. The patron saint of hip-hop and high fashion.

A$AP Rocky and Rihanna, 2022 Met Gala

A$AP Rocky and Rihanna reign supreme as the most fashionable power couple in the game. What’s better than one fashion killa? Two.

Notorious B.I.G. in BAPE

Which rapper wore BAPE first? The question continues to spark debates among hypebeasts. In reality, the Notorious B.I.G. was draped in BAPE way back in 1997. I got the fascinating backstory—and this awesome image from Shawn Mortensen—for the book.

This piece originally appeared in Harper's Bazaar USA