“It’s all about pythons for this season,” Lil’ Kim says, modeling a swimsuit apparently fashioned from snake skin with violet mink balls dangling near her crotch. Others modeled in her second appearance for MTV’s House of Style in 2000 from Gucci and Dolce & Gabbana are made of suede or patent leather croc. Naturally, none of these can be worn in water but, in Kim’s words, they “look good on the saaaaaand.” 

The Queen Bee – known just as much for what she was wearing as what she wasn’t – studied the glamorous looks of Dorothy Dandridge, Marilyn Monroe, Eartha Kitt, Josephine Baker and Mae West, building up her cred as a sexually fearless provocateur and becoming the blueprint for fashionable female emcee. “Marilyn Monroe was a gorgeous actress, gorgeous entertainer,” Kim explained of her style inspiration to Jet magazine in 2000. “She was known for her sexy dressing and courageous personality, wild and not caring. Plus a lot of my style comes from my mom. She’s got a great sense of style.”

However, the way she built her look was borne out of a childhood full of struggle. She famously got breast implants in the late ‘90s, making her the target of the media. “I have low self-esteem and I always have,” she told Newsweek in 2000. “Guys always cheated on me with women who were European-looking. You know, the long-hair type. Really beautiful women that left me thinking, ‘How I can I compete with that?’ Being a regular Black girl wasn’t good enough.”

The rap star was also largely spurned by her father growing up, and after her parents got a divorce, despite her wish to live with her mom, she landed in her father’s custody. “It was like I could do nothing right,” she explained to Newsweek. “Everything about me was wrong – my hair, my clothes, just me.” At 14, she left home and ended up running errands for (and living with) drug dealers to make ends meet.

It wasn’t until she met Christopher Wallace, aka The Notorious B.I.G., and rapped for him impromptu on a Brooklyn street corner that she began to find her confidence. The unlikely pair began dating, and Kim began recording with his Junior M.A.F.I.A. posse, slowly transforming into the wig-sporting, blue-contacts-wearing bombshell who dipped it low in a leopard bikini for her 1996 album Hard Core and later shocked at the MTV Movie Awards with a purple nipple pasty. (Both of these looks were courtesy of her longtime stylist Misa Hylton.)

“That MTV Awards show helped me,” she says. “My name got even bigger. It is all about fashion and my creative style. Guys want something to look at and girls want some kind of inspiration and style. Sex sells. People have to understand that this is how I came into the game. This is my image. I don’t walk in the streets like that. But when I have shows, that’s entertainment, and that’s what I do. God knows we are not perfect and He knows our hearts. When it comes time for me to cover up, I will.”

“Marilyn Monroe was a gorgeous actress, gorgeous entertainer. She was known for her sexy dressing and courageous personality, wild and not caring. Plus a lot of my style comes from my mom. She’s got a great sense of style” – Lil’ Kim

That time was not in 2000, however. And it’s fun to see Lil’ Kim weeks out from her album release for The Notorious K.I.M. be her cute self, body confident and ready for the nearest chaise longue.