Listen Live
Stone Soul 2024
99.3-105.7 Kiss FM
Lil' Kim Fashion Issue Cover

Source: Creative Services / Getty

It was the summer of 1999, and Lil’ Kim had returned to the studio to rerecord tracks for her long-awaited sophomore disc The Notorious K.I.M. after several songs from the haughty and critically-acclaimed project had been leaked online. Around the same time, famed photographer David LaChapelle launched his New Photographs exhibit at the Tony Shafrazi Gallery in NYC. Among the collection was a portrait of Kim posing nude with the LV monogram scattered across her flawless mahogany skin. It immediately caught the gaze of then Interview Magazine editor-in-chief Ingrid Sischy, who “demanded” LaChapelle pull the image and give it to her for the November cover of Interview Magazine. LaChapelle persuaded Kim to let Sischy use the image for the Andy Warhol glossy—a pivotal moment in Kim’s 27-year career that bridged the gap between Hip-Hop and high fashion. Lil’ Kim’s early collaborations with luxury designers like Giorgio Armani, Donatella Versace and Marc Jacobs laid the foundation for every female rapper who’s come after her.

It was only three years prior that Kim had become a fixture on the walls of grown men and teenage boys around the world. If you let Lil’ Kim tell it, she wasn’t “posing” in the iconic Hardcore leopard bikini, she just “dropped down into that pose naturally because that was just who I was,” the petite femcee revealed during a candid sit-down with host Aria Hughes on Complex Con(versations). The itty bitty bikini was a piece from contemporary costume designer Patricia Field’s NYC boutique, where Kim and longtime stylist and friend Misa Hylton shopped “every day.”

Kim’s Hardcore disrupted the 90s female rap landscape, with its sex-laced stanzas and risqué cover image. Fierce femcees like Queen Latifah, MC Lyte, Salt N’ Pepa and Roxanne Shanté—many from whom Kim drew creative inspiration—were all stylish in their own right, but we had yet to see a Black woman dripped in diamonds and fur while rapping about things we only bragged about with our girls. Kim’s sexy style offered a stark contrast to Queen’s patterned Kofi or Lyte’s bucket hat and loose-fit clothing.

“Salt-N-Pepa had the sexiness I knew I had,” Kim revealed about her musical muses during an interview with Talib Kweli on Uproxx. “See MC Lyte was always rough — she didn’t really care to be nothing else, but like look ‘I’m just a rough chick with a pretty face.’ That’s who she was and wanted to be. But Salt-N-Pepa had everything I kinda was. I was sexy with the rough edge but I knew I was different from both of them completely.”

Kim’s unorthodox approach to female rap resonated with Black women who sought to break out of the traditional feminist archetype.

“Her entry into the game was a turning point for women in rap where image became so much more of a focus, like showing sexuality and being stylish also,” explains Clover Hope, author of “The Motherlode: 100+ Women Who Made Hip-Hop.” In the series of essays, Hope deconstructs how each individual rapstress contributed to Hip-Hop. “It was aspirational. It was this coveting of luxury that she epitomized in a way that I think reflected a lot of young Black girls’ desire to be draped in some of these things. A lot of that, the ghetto fabulous philosophy, was young Black girls wanting to live the fantasy outside of what was expected of them.”

In her 1999 novel, When Chickenheads Come Home to Roost: A Hip-Hop Feminist Breaks It Down, writer Joan Morgan, who coined the term “hip hop feminist,” examined the complex duality of feminism.

“We need a voice like our music – one that samples and layers many voices, injects its sensibilities into the old and flips it into something new, provocative, and powerful,” she wrote. Kim’s salacious style and image, though crafted from the male gaze, offered a new version of feminism with a woman’s sexual prowess at the forefront. All of which contributed to the Queen Bee’s success and enduring legacy on fashion and Hip-Hop.

A Match Made In Fashion Heaven

MCM Global Hosts Premiere Of “The Remix: Hip Hop X Fashion” At Tribeca Film Festival

Source: Theo Wargo / Getty

It’s impossible to talk about Kim’s influence on fashion without mentioning Misa Hylton, the style architect who is responsible for many of Kim’s iconic looks. The two first met at Misa’s Scarsdale home circa 1993-1994 while the Notorious B.I.G. was in the process of recording his debut album with Puff Daddy. “Kim came and she was hanging out at the house and she was so fly and her hair was fly.” Misa and Kim “shared the same taste,” which was the foundation for their effortless collaborations. They naturally made magic together.

Misa is the mastermind behind Kim’s leopard bikini, her prismatic clothes in Crush On You, the Swarovski-embellished catsuit she wore to the 1999 Source Awards (inspired by Nija Battle’s furs) and the lavender pasty and jumpsuit she wore to the 1999 MTV Video Music Awards. The astonishing look might have been inspired by Missy Elliott, but it was carefully designed by Misa, who “wanted to make something really ornate and feminine and pretty, to offset the fact that she had one breast out,” she told PopSugar. A coloring mistake by Kim’s then-hairstylist Diane Alexander turned her typically-blonde wig purple, creating a look that has become one of the defining images of Kim’s career.

Singer/rapper Lil'' Kim

Source: Trevor Gillespie / Getty

“Her introduction of sexy and ghetto fabulous to the hip-hop culture of the ‘90s was groundbreaking and revolutionary,” said die-hard Lil’ Kim fan and celebrity creative director Paris Chea when asked about Kim’s fashion legacy. “Trends her and Misa Hylton created are timeless and still being copied ‘til this very day. To be iconic, one must always be consistent, and Lil Kim for sure has always been that.”

The Crossover

Kim’s work with David LaChapelle in 1999 also provided the framework for her high fashion relationships.

“I introduced Lil’ Kim to Giorgio Armani and it was a big, big deal when that happened,” LaChapelle told journalist Nadja Sayej in a 2018 Garage.Vice interview where he broke down the behind-the-scenes fashion moment that put Lil’ Kim on the radar of the Italian designer. “There wasn’t this connection between rap music and high fashion back then; it didn’t happen yet. Now, everyone works hard to be seated next to Anna Wintour at Fashion Week.”

Opening Night of "Gypsy Passion"

Source: Ron Galella / Getty

Earlier this year, Kim recalled to HelloBeautiful what it was like being embraced by designers like Donatella, Marc Jacobs, Alexander McQueen and John Galliano. “They embraced me quickly in my career and it was at a time where a lot of musicians were not being embraced by the major designers. I’m one of the first ones next to Diddy.”

The trendsetter joyfully reminisced about the first time she met Marc Jacobs and how he recited the words to her fan-favorite How Many Licks.

“The fashion world has always used music as their motivation because I know when I used to fit and me and Marc [Jacobs] would have lunch in his showroom while he was creating looks for one of his fashion shows, he would always be playing my music,” Kim told us. “He would be playing How Many Licks, and I would be like, ‘You know this song?’ He would be like, ‘Girl, please!,’ and that’s when I first met him. I was so shocked, but I was more shocked that he knew almost every song!”

“Lil Kim was an icon of the ‘90s and was a serious trendsetter, wearing Chanel runway, Dior, and Versace looks young artists continue to emulate to this day,” said Claire Sulmers, founder of The Fashion Bomb Daily. “She was partying with Donatella Versace and even rocking head to toe Louis Vuitton monograms in a time when our community was just getting familiarized with European design houses.”

Hair To Stay

Beyond using fashion as a means of expression, Kim’s daring hairstyles became an extension of her luxurious lifestyle, working with several hairstylists who helped craft her most memorable ensembles. In a 2013 interview with Vice, celebrity hairstylist Eugene Davis—who worked with everyone from Mary J. Blige to Aaliyah at the time—opened up about the inspiration behind Kim’s multicolored hair in “Crush On You.”

“The stages on set turned from blue to green to yellow to red and I saw that her clothes were like that too. I was like, “’You know what Kim, we need to do something crazy and different.’ I left Long Island City where we were shooting, went back to New York, bought some wigs, put them on her and recut them on her. That video became legendary.”

We also caught up with the colorful wig connoisseur, who described Kim’s approach to hair as “adventurous. “Kim was imaginative and was open and willing to trust her glam team. Did we always want to set the bar high? Yes and it went perfectly with Kim artistic vision of her unique spin on style, hence starting the whole “Crush On You” color hair trend. Which is still currently trending, Kim did it first.”

Kim’s hairstyles quickly became as equally iconic as her designer threads. The looks crafted by Davis, (think: Mary J. Blige’s updo in Not Gon’ Cry) became the poster image for hair in the ‘90s.

Her famous blue Chanel wig was a craft-store creation by Dionne Alexander, who told Complex, “That was a blonde wig that I dyed those colors with the brown and the black.” She added, “And don’t ask me how I knew to do this, because I don’t know. But I went to the arts and crafts store, I purchased some thick tracing paper, and I cut out the Chanel logo and then I used magic marker to put it on the wig. That’s my secret.”

According to Hylton, luxury branded hair was a natural progression on Kim’s fashion trajectory. “Colored hair and designer brands were really a part of Kim’s DNA, so this was a natural progression of combining those two elements. It was the manifestation of our work together from a place of authenticity and intuition,” she revealed in a 2019 Essence chat.

The Blueprint

Kim‘s ability to coexist as an exalted player in both the fashion and music industries provided the blueprint for today’s female rap stars, who understand the stratospheric effect of fashion. Cardi B, Nicki Minaj, The City Girls, Saweetie (and so many more) are all products of Kim’s pioneering foray into high fashion.

“She made fashion come to her,” explained Hope. “Her and Misa…Misa designing these custom outfits at that time, (some of what I cover in my book). I talked to stylists including Misa and Eve’s stylist and they talked about high fashion brands weren’t loaning to rappers. They weren’t readily being like ‘I want so and so to wear my clothes.’ It was harder to get those European brands. Now, fashion is falling over itself trying to get Cardi B to wear something. I think the role Kim played led to a place where high fashion wants to have the hip-hop name attached to it.”

Today, Kim is applying everything she learned about fashion into her collection with PrettyLittleThing. The queen teamed up with the fast-fashion retailer to create a collection that would resonate with her core fans.

Pretty Little Thing X Lil' Kim

Source: PrettyLittleThing / PLT

“The thing I love is that it’s a little bit of me mixed with PrettyLittleThing. You guys can get beautiful looks that are so affordable,” Lil’ Kim said in an official press release. “I wanted to stay true to the PLT aesthetic and show everyone that I’m a real stylist and visionary. This collection was designed by me and I’m super proud of that.”

There’s a current petition with nearly 5,000 signatures calling for the CFDA to bestow Kim with the Fashion Icon award.

“My fans are beasts and I love you guys to the heavens. Whether that happens or not, I’m going to keep stepping and doing what I do in fashion and being fly. That’s never going to change. I love clothes,” she told Refinery29 in 2019.

When Kim isn’t repping her borough BK to the fullest as the Brooklyn Nets’ newest ambassador, she’s lending her voice to BET’s American Gangster: Trap Queens and enjoying the view from the throne, reigning forever as the queen of rap.

| More From Our Fashion Issue |

The Anatomy Of An Icon: Lil’ Kim’s Enduring Influence On Fashion & Hip-Hop

The Importance Of Black Fashion Pioneers Like Ann Lowe And Zelda Valdes

Joyce Bryant Isn’t A Throwback, This Diva Is Black History AF

Misa Hylton: From Bad Boy Stylist To Global Creative Partner For MCM

The Anatomy Of An Icon: Lil’ Kim’s Enduring Influence On Fashion & Hip-Hop  was originally published on