Lil Kim Through The Years

Lil’ Kim, through the years, has given us iconic fashion moments that have transcended generations. At the height of her career in the 90s and 2000s, the trendsetting femcee laid the blueprint for female rappers with her sexy lyrics and braggadocious style. Kim is a trailblazer, a one-of-a-kind act, and the reason rappers, today, can have relationships with top designers. “I introduced Lil’ Kim to Giorgio Armani and it was a big, big deal when that happened,” famed photographer David LaChapelle shared in an interview with Garage.Vice. “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.” Before Kim, brands wouldn’t lend clothes to Hip-Hop artists. Lil’ Kim became the muse of iconic designers like Marc Jacobs, who remains one of her closest friends today. Kim recently revealed Marc is set to pen the forward of her upcoming memoir.

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“Style for me means everything, said Kim on the set of her latest cover shoot with Ebony Magazine. “I literally hit it off with Marc Jacob, I hit it off with Donatella; they’re still my best friends to this day. I didn’t think they would embrace me so fast.” In our 2021, Anatomy Of An Icon cover story, we chronicled Lil’ Kim’s enduring influence on Hip-Hop and fashion. Paris Chea, who styled Kim for her controversial 2023 Ebony Magazine cover, credited Kim with bringing ghetto fabulous to the forefront. “Her introduction of sexy and ghetto fabulous to the hip-hop culture of the ‘90s was groundbreaking and revolutionary,” said the celebrity creative director. “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.”

Lil Kim Through The Years

In 1999, Kim graced the plush red carpet of the Met Gala wearing Versace. Kim’s provocative pink look personified that year’s “Rock Style” theme. As a guest of Donatella, that year, the designer created Kim’s custom pink mink that became a standout look. “The mink coat was an original you won’t find it anywhere,” Kim told Vogue. “I’ve never seen it in stores.” Lil’ Kim’s iconic 1999 VMAs look also goes down in history. It was the purple pastie seen ’round the world. Inspired by a Missy Elliott joke, Kim and her then-stylist Misa Hylton cooked up a head-turning look that not even Diana Ross could resist. Diana tapping Kim’s breast is not only an iconic fashion memory but a pop culture moment for the ages. “I was with Missy Elliott, and we were talking fashion and music, and she was like, ‘If I was Kim, I would just have one boob out, like f–k it. I wouldn’t care, because Kim can do that.’ Missy got my imagination working,” Misa revealed to PopSugar. “The next big event was the 1999 VMAs, and I brought that idea to life. It was risqué, so I made it really pretty with Indian bridal fabric to soften it.” Kim’s influence permeated the beauty world as well. The lavender wig she wore to accompany her famous VMAs look was an accident that would serve as the outline for female rappers to come. Kim’s then-hairstylist Dionne Alexander was the mastermind behind many of Kim’s trendsetting wigs, some of which she designed with Sharpies. “She was not afraid to change. I could bring five different wigs in, and she’d love and want to wear all of them. It was no problem, I didn’t get a lot of pushback. It was the best thing ever — I was able to express my creativity,” she revealed in a 2023 PopSugar interview. “You can’t dye synthetic wigs, so back then, I was using a lot of Sharpies and magic markers.”

Misa Hylton And Kim

There should be college courses dedicated to Kim’s indelible mark on fashion. And style architect Misa Hylton would teach it. Misa and Kim formed a friendship that would be the foundation of their creative genius. Misa often talks about that era, and how they used to purchase everything they owned. They were, in their words, “true fashion girls.” “When it was time to do a music video, Kim would bring along her belts, I’d bring all my shoes. I would bring my fur, she would bring her fur. Un would bring his wife’s jewelry,” Misa explained in an interview with Complex detailing her and Kim’s love for the “powerful femininity” of Chanel. “That’s how we made it happen. It was all very authentic, and all those pieces were our own. When you saw us wearing things, they were our own. There was no such thing as pulls and studio services that we’re able to do now. Those weren’t options for us in the beginning.” Check out more photos of Lil’ Kim through the years.

1. Lil' Kim, 1997

Lil’ Kim’s “Crush On You” look was a defining moment in her career and pop culture. Unafraid to make bold hair choices, as well, here she is rocking a colorful wig, monochromatic bikini, pearl Chanel chain belt, and fur. 

“We would buy our own pieces,” Misa explained to Complex. “And Chanel was a lot less expensive back then, by the way. A hell of a lot less expensive. I feel like a drawstring bag was like $1,500, which is the price of a nice shoe now. Now they’re, like, what, five to seven thousand? I mean, back then, $1,500 probably felt like $5,000.

2. Lil' Kim, 1997

Lil’ Kim performed at the Big Beat/Atlantic Records showcase, in 1997,  at the Impact Music Convention wearing her signature 90s look — an all mesh dress that revealed her bikini and round sunglasses. 

3. Lil' Kim, 1998

Who else could make a Diamond encrusted basket mask this chic? Lil’ Kim attended the 1998 Lady of Soul Music Awards in this eye-popping metallic look. Kim accepted the award for the “Not Tonight Remix” and thanked God and Puffy in her acceptance speech.

4. Lil' Kim, 1999

Lil’ Kim wore Versace to the 1999 Met Gala. The custom pink look is one of the most recognizable Met Gala looks, cementing the Hardcore rapper in the fashion history books. Lil’ Kim was the first rapper to attend the Met Gala. Kim opened up about the iconic look to Vogue, saying, “At the Met, you’re a designer’s muse [and] she loved the fact that I have fun in her clothes. Versace was one of my favorite designers. She knew that and would always create things tailor-made just for me.”

5. Lil' Kim, 2001

Lil’ Kim’s 2001 Source Awards look is iconic because, sure, she wore her boobs out again, but her hair was attached by a zipper! On the red carpet, Kim dropped the bar, “to anyone who has something to say, zip it up.”

6. Lil' Kim, 2001

2001 was a time! Kim attended the MTV Movie Awards in this jaw-dropping top that turned heads because it was holding on by a thread – literally.

7. Lil' Kim, 2003

It’s safe to say Lil’ Kim invented the nip slip. Here she is in 2003, showing off her tight physique in a barely-there skirt and string monokini.

8. Lil' Kim, 2006

Lil’ Kim’s VMA looks always hit and this corset fit doesn’t miss. In 2006, Lil Kim had returned home from serving a jail sentence of one year and a day and came back looking like she didn’t miss a beat. 

9. Lil' Kim, 2008

Lil’ Kim put the low in low rise at the 2008 BET Awards. Kim hit the stage to perform “Let It Go” with Keyshia Cole wearing metallic pants and a midriff. 

10. Lil' Kim, 2010

Lil’ Kim popped out in 2010 for a Three Olives Vodka Purple photo shoot at Drive-In Studio where she wore a purple bodycon dress with plunging neckline. With her hair and makeup more natural, Kim was showing a stripped down version of herself. 

11. Lil' Kim, 2015

After what felt like a hiatus out of the spotlight, Kim reemerged at the 2015 BET Awards in her iconic squat pose to celebrate Bad Boy and Diddy in a performance that was like a coming-out party for the icon. Kim returned with a vengeance to collect her flowers. 

12. Lil' Kim, 2023

Hip-Hop turned 50 this year and it wouldn’t have been a celebration without Lil’Kim who hit the stage to perform at Yankee Stadium in this Gucci look and thigh-high patent leather boots.