A Look Back at Lil' Kim's Most Iconic Outfits, From Runway To Red Carpet

Lil' Kim's demeanor always lets people know she has the It factor. Even early on in her career, when she and stylist Misa Hylton weren't yet respected in the fashion industry due to being women of color, Kim always showed up serving looks and sex appeal. She's talked about sex so eloquently that she's given the word "vulgar" a pretty face. And with her transition into fashion, she has later become an icon.

When the artist arrived at the 1999 VMAs in the lilac jumpsuit with one breast out, she gladly told an interviewer, “I just thought that I’d do something that could say, 'Look at her.'” Decades later, the duo have surely secured their throne in fashion history. “We were always ready to push fashion boundaries,” Hylton told HYPEBAE in 2019.

Her Hard Core debut

Kim's debut album was Hard Core, both literally and figuratively. The album cover art featured the artist in a cheetah print lingerie set, squatting in a pose that revealed much more than women would at the time. The album cover was selected by her mentor and lover, the Notorious B.I.G. In his eyes, the image was the perfect touch to Kim's raunchy lyrics. It was at this point that Kim began to perfect her formula of sex appeal, from her lyrics to her looks.

Evolving into her signature aesthetic

After Biggie’s unfortunate death, Kim's public image shifted from being the late rapper's hot female artist to a raunchy icon who would soon be seen frolicking with designers like Giorgio Armani. Everything from loud pops of color to fur trims and animal print was Kim's aesthetic. The girls just knew that no one could pull off what she wore even if they tried. With the close relationships she's built, she would always pop out in something custom, loud and sexy.

In 1999, Kim attended the Source Awards. Her stylist Hilton reminisced the look with Essence in 2020: "You couldn’t help but be inspired by Nija Battle’s furs. I saw this freshly dyed tan-colored fur and envisioned a nude bodysuit on Kim. I embellished the bodysuit with Swarovski crystals to give this effect of being showered in diamonds. A platinum wig and tan and cream cuffs pulled the look together flawlessly."

Later that year, Kim was the first female rapper to attend the Met Gala, and she attended the star-studded event as Donatella Versace’s muse. “Donatella is my girl. We’ve loved each other from the moment we first saw each other,” Kim shared with Vogue. "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.” Kim later attended the event as Marc Jacobs’ muse as well.

By the 2000s, the new queen of rap had found her footing in the world of high fashion, and not as a showpiece. Kim was establishing bonds with fashion houses as she simultaneously built her empire. She became “that girl” every young girl wanted to be. Not just every girl from the boroughs of NYC, but now, the world.

No longer could people ban Kim for her expressive lyrics or call her “distasteful.” She's talented and now, even more visually appealing. Designer Marc Jacobs and Kim became so close that while in jail, Kim would send Jacobs drawings of Bratz dolls in his designs. He'd blow them up and post them around his home.

Although Kim has taken a back seat in the rap game to let future generations get some playtime, her influence continues to reign through artists like Beyoncé and Cardi B. Her presence has always been unexpected. And 20 years later, it's clearly still holding its weight in headlines.