A Celebration of Lil Kim and Bad Boy Style


The worlds of fashion and hip hop have long been intertwined, and in many ways we have the Bad Boy family of artists to thank for that. The record label founded by Sean Combs (aka Puff Daddy aka Diddy) has represented legends including Notorious B.I.G. and Lil Kim, who are as well known for their distinctive style as they are for their verses—which often contain shoutouts to luxury fashion labels.

The fashion-hip hop relationship is symbiotic. If you think about it, the general public’s primary exposure to a luxury company like Gucci is hearing rappers mention it in their lyrics, or seeing rappers wear the brand. From Karl Lagerfeld’s streetwise Chanel Fall/Winter 1991 collection to Marc Jacobs’ show in Harlem (where Lil Kim held court in the front row), we’ve witnessed hip hop style trickle up to the runways, too. In honor of these legends, we’re paying tribute to the enduring style legacies of our favorite Bad Boy artists.


“Who got y’all rocking the Prada, the Dior, Chanel, Versace and Louis,” raps Kim on her track “Heavenly Father.” That’s just the tip of the iceberg with Kim, who is officially the top brand-dropping MC of all time—and she’s got the closet to back it up. Long before Rihanna and Nicki Minaj were front row fixtures, the “Queen Bee” was crushing it on the fashion week circuit, making frequent cameos at Marc Jacobs, Versace, and more. Kim is perhaps the most enthusiastic “label whore” out there. The pint-sized diva rode the crest of logomania during the late nineties and early aughts, often wearing head-to-toe LV or Fendi (as seen above). She took her Versace dedication to the next level, perched front row at the brand’s Spring 2001 show in a wig stamped with Versace’s graphic vector motif.

Chalk it up to fashion’s ongoing 90s obsession, but Lil Kim’s audacious, DGAF-glam style feels more relevant than ever now. Take her infamous pasty moment for example. When Anthony Vaccarello sent out a crystal-studded pasty look for his debut Saint Laurent collection, we immediately flashed back to Diana Ross jiggling Kim’s boob onstage at the 1999 VMAs. Ditto goes for when Nicki Minaj turned up at Haider Ackerman’s Fall show with one exposed breast covered only by a metallic square. Who wore it best?


There’s no questioning the late, great Christopher Wallace’s influence on fashion. His baby picture (the one from his “Ready to Die” album cover) is printed on a Supreme t-shirt. In 2014, Rag & Bone did a collaboration with COOGI directly inspired by the label’s patterned sweaters that Biggie made famous. Countless designers play Biggie on their runway or after party soundtracks.

In one of his biggest hits, “Hypnotize,” he raps “I put hoes in NY onto DKNY. Miami, DC prefer Versace. All Philly hoes go with Moschino. Every cutie with a booty bought a COOGI.” Donatella Versace has gone on the record appreciating the visibility he gave her brand. “I loved what he was doing and how he was giving people a way to know about Versace,” she said. “I do think a lot of people started to know about Versace because of him.”


Embodying his group’s flashy style, Sean Combs became known for wearing multiple iced-out chains, ultra baggy jeans, bucket hats, and luxe furs in the late nineties. Recall: the music video for “More Money More Problems.” As his business career evolved, so did Diddy’s look, which veered in the direction of slim suits—always complete with a touch of bling. He launched his Sean John collection in 1998, which earned Combs a CFDA Award for Menswear Designer of the Year in 2004. He also dated supermodel Naomi Campbell at one point, which is totally noteworthy in our book. At the end of the day, you’ve got to respect Diddy as the original architect behind the Bad Boy empire.


In discussing the bad gals of Bad Boy Records, Lil Kim was always the Queen Bee of fashion, and she’s a very difficult act to follow. But soulful crooner Faith Evans (who was married to Biggie) deserves her own honorary mention. She’s always had a true gift for tasteful brown lip liner, and should be on every 90s hairspiration Pinterest board. Evans has been looking equally fierce on the Bad Boy reunion tour this year.


The word “jiggy” comes to mind when describing Mase’s style. Puff’s right hand man has never been afraid to take a fashion risk, and loves an over-the-top moment, whether it be a luxe fur, green leather tracksuit, or full-on camo fatigues.


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