Lil’ Kim’s Best Fashion Moments of All Time

From lyrics to looks, there’s nothing that Lil’ Kim has shied away from. Since her breakout as part of the Notorious B.I.G.’s Junior M.A.F.I.A. group in 1994, the Brooklyn-born rapper has made plenty of statements, many of them sartorial. 

Her 1996 debut album “Hard Core” featured the artist in a see-through lace top (no pants — long before it was a trend), perched on a bearskin rug. An accompanying poster of Kim dressed in a leopard-print bikini and matching marabou-trimmed robe (and posed in a particular way) became an infamous item that countless fans hung on their bedroom walls.

From there, the rapper unveiled a steady parade of looks that continue to this day — especially for the 50th anniversary of hip-hop, which the artist will celebrate by performing at the Hip Hop 50 Live concert at Yankee Stadium on August 11.

If there was one word to describe Lil’ Kim’s style, it might be “adventurous.” Through the years, the 49-year-old artist has found countless ways to innovate her personal style and reinvent the idea of shock fashion. That includes barely-there clothing, yes, but also new beauty looks, plus plenty of. Long before it became mainstream to wear pink hair, pair knee boots with no pants, or experiment with bondage-style garments, Lil’ Kim was trying it all.

The rapper’s sartorial secrets and behind-the-scenes moment are likely to be a big part of her forthcoming memoir, “The Queen Bee.” While the tome has been in the works (and delayed) for some years now, the artist recently unveiled a finished manuscript, revealing a foreword by friend Marc Jacobs. The book is currently slated for release in September 2025.

Until then, here’s a look at some of Lil’ Kim’s best fashion moments through the years.

In Versace at the 1999 Met Gala

The Met Gala’s theme in 1999 was “Rock Style” — a somewhat open-ended topic, but Kim’s look managed to capture the meaning of it through a contemporary lens in which hip-hop was taking over the music industry and redefining the idea of the traditional rock star. “The Met was almost like a secret society, not everyone got invited. It was this upscale, elite society event,” Lil’ Kim told Vogue in 2020, when reflecting on her outfit that year, a head-to-toe Versace look that included a pink leather studded bra and hot pants, a pink fur coat and pink-tinged python knee boots with a pink heel detail. The rapper also revealed in the interview that the boots came direct from the runway, meaning they were a sample size eight instead of her usual size 4 1/2 or 5. “I told her I don’t care because I knew she wanted me to wear them,” Kim said of working with Donatella Versace to pull together the look.

The infamous one-breasted jumpsuit for the 1999 MTV Video Music Awards

The same year, Kim showed up to the 1999 MTV Video Music Awards in a look that would become one of her most famous. The artist’s stylist Misa Hylton designed a jumpsuit using an Indian embellished fabric in a lavender hue. Its asymmetrical shape only covered one breast; the other was covered with a matching nipple pasty — which would become instantly famous when fellow presenter Diana Ross touched it live on camera while the two were onstage with Mary J. Blige. Hylton gave Kim a pair of sparkly platforms, which also matched the artist’s purple hair for the event.

At the 1998 Soul Train Lady of Soul Awards

Lil’ Kim’s personal style has been undeniably defined by key beauty looks, but it’s not just about hair — the rapper has also proven the value of a well-placed accessory, especially an out-there headpiece. At Soul Train’s 1998 Lady of Soul Awards, Kim showed upon the red carpet in a silver metallic dress with a high-low hemline, revealing matching silver metallic ankle strap heels likely customized for her with crystal fringe accents. The pièce de résistance? A matching crystal accented caged headpiece that the rapper wore over her platinum blonde hair.

Glammed out at the MAC Cosmetics “Viva Glam” 2000 Campaign Party for HIV/AIDS Research

Alongside friend and colleague Mary J. Blige, Lil’ Kim served as a longtime ambassador of MAC Cosmetics’ Viva Glam campaign, which supported HIV/AIDS research. At a 2000 party at Mr. Chow in New York celebrating the partnership, the rapper showed just how glam she could get, showing up in a leopard print mini dress adorned with a crystals and a matching crystal hip belt and jewelry. It wasn’t her only matching moment of the evening: A pair of metallic red knee boots also coordinated with the gold metallic briefs — and red lipstick kiss prints — sported by a group of male models who posed with her.

In head-to-toe PVC for the 2000 MTV Video Music Awards

After the Diana Ross jumpsuit moment in 1999, Kim followed up at the MTV Video Music Awards the next year in a dominatrix-inspired look that was plastic fantastic, from the caged bodysuit all the way to her ankle-wrap PVC heels.

In matching Fendi for a video shoot

Like many hip-hop artists, Lil’ Kim’s wardrobe has consisted of a lot of custom pieces, done by the likes of designers such as Dapper Dan, known to take designer logo pieces and rework them into full-look coordinating pieces. While a thigh-high logo boot, matching jacket and headband are items that are typically part Fendi’s offering nowadays, this 2001 outfit from a music video shoot was likely a custom look for the music artist.

White boots and Chanel at a 2000 charity event

Lil’ Kim matched her black-and-white Chanel accessories to a black laser-cut leather skirt and white foldover boots at a 2000 charity event at Cipriani in New York. The rapper was arguably the first to wear — and rap about wearing — the French luxury brand.

In hair-covered boots at the 2001 Soul Train Lady of Soul Awards

With MSCHF’s viral boots, GCDS’s jaw heels and Loewe’s balloon shoes, we are currently in an era of surreal fashion. But Lil’ Kim was already going down the rabbit hole back in 2001, when she sported a pair of white heeled knee boots with bits of hair extensions hanging off of them (and matching her own red and pink hued hair).

In a muscle bodysuit at the 2022 BET Awards

After something of a hiatus, the artist has been back in the spotlight, including at last year’s BET Awards, where she walked the red carpet in a trompe-l’œil bodysuit decorated with muscle and hair detailing. Kim paired it with Versace heels and an Hermès Birkin bag to match her green hair.

For a look at more of Lil’ Kim’s best fashion moments, click here.