7 of lil’ kim’s most iconic outfits

The rapper's jaw-dropping looks are often imitated, but never duplicated.

by Brittany Natale
11 July 2019, 3:04pm

Since the release of her debut studio album Hard Core in 1996, Lil’ Kim has been paving the way for female rappers and singers alike. From humble beginnings living on the streets in Brooklyn, she went on to win dozens of awards and make history with her head-turning looks that have inspired everyone from Beyoncé to Cardi B. From her fluorescent wigs to her lux furs, she continues to influence a new generation with her legendary style, and of course, her boundary-pushing music.

In honor of Lil’ Kim’s birthday, i-D takes a look at just some of this icon’s many memorable style moments:

1999 MTV VMAs
Twenty years later and Lil’ Kim still has everyone talking about the purple ensemble she wore to the 1999 MTV Video Music Awards held at the Metropolitan Opera House in New York City. Designed by her stylist, Misa Hylton, the outfit featured a one-shouldered jumpsuit, tons of lilac and silver sequins, a matching wig, and that iconic purple pastie. That night Lil’ Kim presented the award for Best Hip Hop video alongside fellow music powerhouses Mary J. Blige and Diana Ross.

“Supa Dupa Fly” Music Video
Lil’ Kim proved that fellow rapper, friend, and collaborator Missy Elliott was not the only one with next-level style in Elliott’s 1997 video for “Supa Dupa Fly” — Lil’ Kim made a memorable cameo in the Hype Williams-directed visual wearing black and white Chanel suspenders paired with bright red trousers, a gold chain belt, and matching oversized Chanel sunglasses. The outfit was so influential that another music maven, Beyoncé, wore a replica of the outfit for Halloween in 2017 as a tribute to Lil’ Kim.

1999 Met Gala
Lil’ Kim was a risk taker even while attending the Met Gala in 1999 when she showed up wearing a full-length pink Versace coat, snakeskin boots, studded hotpants, and a matching pink wig. The annual fete kicked off the Met’s “Rock Style” exhibition which navigated the influential style of famous musicians throughout the years. Some of the items on view included Madonna’s Jean Gaultier bustier designed especially for her 1990 “Blonde Ambition” tour, and Alexander McQueen’s Union Jack suit he created for Bowie’s 1996 “Earthling” tour. Nearly two decades later Lil’ Kim’s style would also be exhibited in a museum setting — her unforgettable money manicure by nail artist Bernadette Thompson was shown at the Museum of Modern Art in 2017 as part of its “Items: Is Fashion Modern?” exhibition.

1999 VH1 Vogue Fashion Awards
For the 1999 VH1 Vogue Fashion Awards Lil’ Kim wore a spectacular rhinestone-encrusted skirt and bodice complete with matching stole and glitter headpiece. It was this same evening that Alexander McQueen famously bowed down to her exclaiming that she was his idol after she presented him with the Fashion Designer of the Year award.

Stenciled Chanel and Versace Hair
Throughout the years Lil’ Kim has become known not only for her trendsetting outfits that continuously push the envelope, but also for her countless colorful wigs. Whether she is donning a green wig complete with a full-on green outfit, or opting for an art-forward “zippered” ‘do, Lil’ Kim makes waves with each hairstyle she chooses. Some of her most memorable ones include her Chanel and Versace wigs in which she stenciled the luxury fashion houses’ logos directly onto her bangs.

“Crush On You” Music Video
During her 1997 video for “Crush On You” fans everywhere were introduced to the more colorful side of Lil’ Kim — it is said that this is the video where she first debuted the vibrant wigs that she soon became synonymous with. The video, which was directed by fellow Brooklyn native Lance "Un" Rivera, was inspired by the 1978 fantasy film The Wiz and featured various sets in bright primary colors. Lil’ Kim worked with Hylton and her hairstylist, Eugene Davis, to create outfits and wigs that coordinated with each shot, coming up with separate blue, green, yellow, and red ensembles to wear for each. In this photograph taken by Anderson Ballantyne, Lil’ Kim is pictured on the Queens, NYC film set in an all-blue fur jumpsuit with a matching bright blue wig. Her hairstyles, however, did not provide the only standout moments in “Crush on You”— a then-20 year old Aaliyah also made a cameo.


2002 Grammy Awards
For the 2002 Grammys Lil’ Kim’s outfit proved that the magic is all in the details by pairing a Chanel motorcycle helmet with her red and white bedazzled ensemble. Later on that night Lil’ Kim would go on to pick up her first Grammy for “Lady Marmalade,” the hit song she performed alongside Christina Aguilera, Mya, and Pink, in Baz Luhrmann’s 2001 blockbuster film Moulin Rouge. In a March 2019 interview with Complex, Hylton shared that she and Lil’ Kim bought many of the designer pieces they wore themselves — there was no such thing as pulls or studio services when they first started out.

Grammy Awards