Lil Kim’s Wildest Award Show Looks Of All-Time — PICS

By:

Christina Casiano

October 7, 2019 7:51PM EDT

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Lil Kim at 1999 Grammys

Lil Kim at 1999 Grammys — Lil Kim is a legend and pioneer for women in rap. And she’s also one of the most iconic awards show attendees of all time. Not for her crazy antics; it’s her wild outfits! Kim is teensy tiny, but she manages to make herself larger than life when she hits the red carpet at an awards show, whether it’s the Grammy Awards, the MTV Video Music Awards, the BET Hip-Hop Awards, or anything in between. She has fun with her outfits, and never shies away from showing some skin while showcasing her sexy style. Take her now-infamous outfit that she rocked at the 1999 Grammys. Kim rolled up wearing a jumpsuit designed by her personal stylist that made her look like a mermaid. The lilac jumpsuit was one-shouldered, and covered in sparkly seashell appliqués. Oh, and her left breast was only covered with one of those seashells used as a pasty! To see more of Lil Kim’s wildest awards show outfits, scroll through this gallery.

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Lil Kim at 2019 BET Hip-Hop Awards

Lil Kim at 2019 BET Hip-Hop Awards — Lil Kim shined in this Gucci tuxedo dress at the 2019 BET Hip-Hop Awards. She perfectly matched her hair to the metallic pink of the high-low dress, and added some height to her tiny frame with platforms.

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Lil Kim at 2019 BET Awards

Lil Kim at 2019 BET Awards — Lil Kim looked like she stepped out of a sci-fi movie with this futuristic Afffair number worn to the 2019 BET Awards. The exaggerated hips, with the addition of clashing Chanel gloves and a bowling ball bag are classic Kim.

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Lil Kim at 2003 BET Awards

Lil Kim at 2003 BET Awards — One of Lil Kim’s most iconic looks: this daring bikini and matching coverup worn to the 2003 BET Awards that made all her haters green with envy. It takes someone special to pull off wearing a scrunchie as an anklet.

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Lil Kim at 1997 Grammys

Lil Kim at 1997 Grammys — Lil Kim looked insanely cool at the 1997 Grammy Awards in this moto-inspired ensemble: red leather pants, a matching, cropped moto jaket and stiletto boots, a bikini top — and a Chanel bike helmet.

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Lil Kim at 2019 MTV VMAs

Lil Kim at 2019 MTV VMAs — Lil Kim made her triumphant return to the MTV VMAs in 2019 after six years away, and made a statement on the red carpet in this purple, feathered bordello dress. Again with the matching hair!

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Lil Kim at 2014 Soul Train Awards

Lil Kim at 2014 Soul Train Awards — Lil Kim smoldered on the red carpet at the 2014 Soul Train Awards in New Orleans in a sassy leather and lace number. Leather shorts, an exposed bra, and feathered boots hit all the notes.

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Lil Kim at 2001 MTV Movie Awards

Lil Kim at 2001 MTV Movie Awards — If you thought Lil Kim’s 1999 Grammys outfit was shocking, it was nothing compared to what she wore to the 2001 MTV VMAs! Kim simply rocked a pair of low-rise jeans, and two pasties covering her chest, connected by chains.

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Lil Kim at 2017 BET Awards

Lil Kim at 2017 BET Awards — Lil Kim was literally glowing at the 2017 BET Awards in a bedazzled bodysuit. The shiny, mesh suit featured long sleeves and a turtleneck top, but it was anything but demure. You could see her bra and thong underneath!

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Lil Kim at 2013 MTV VMAs

Lil Kim at 2013 MTV VMAs — Lil Kim looked absolutely phenomenal at the 2013 MTV VMAs! The rapper paired a leather bodysuit with a frilly peplum, with latex sleeves and leggings She added a wide gold belt and yellow booties.

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Lil Kim at 2004 MTV VMAs

Lil Kim at 2004 MTV VMAs — After years of skimpy ensembles, Lil Kim wore this gown to the 2004 MTV VMAs. Of course, it wasn’t exactly conservative. The ultra low-cut top barely covered her chest, and the flowy skirt was totally transparent.

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Lil Kim at 2001 MTV VMAs

Lil Kim at 2001 MTV VMAs — Lil Kim, seen here holding her Moon Man statue at the 2001 MTV VMAs, rocked an outfit totally of its time: low-rise denim, a graphic crop top, incredibly long hair extensions, and a belt that doesn’t actually hold anything up.

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Lil Kim at 2001 Lady Of Soul Awards

Lil Kim at 2001 Lady Of Soul Awards — Lil Kim waves to photographers as she struts the red carpet at the 2001 Lady of Soul Awards in a seriously crazy outfit. Her satin “dress” is held together only by ribbons. Fishnets, fringe, sunglasses, and pink hair complete the look.

Lil’ Kim waves at photographers as she arrives to the Soul Train Lady of Soul awards as a presenter, in Santa Monica, Calif
LADY OF SOUL AWARDS, SANTA MONICA, USA

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Lil Kim at 1998 Lady Of Soul Awards

Lil Kim at 1998 Lady Of Soul Awards — Lil Kim rocked this intricate headdress, train, and jeweled sleeves at the 1998 Lady of Soul Awards, but it looks like it would all be totally home at the Met Gala, too.

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Lil Kim at 1997 MTV VMAs

Lil Kim at 1997 MTV VMAs — One of Lil Kim‘s most impactful outfits. She rocked this Cleopatra-inspired bikini and headdress at the 1997 MTV VMAs, along with some of her fellow ladies of rap. Cardi B actually recreated this look for her “Money” music video!

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Lil Kim at 1999 Vogue Fashion Awards

Lil Kim at 1999 Vogue Fashion Awards — Vogue didn’t know what hit it in 1999. Lil Kim rolled up to the VH1/Vogue Fashion Awards wearing this mysterious, masquerade outfit that was more lingerie than dress. A fur stole and a crown? Yes, please.

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