From Björk’s Swan dress to Lil ‘Kim’s mermaid surprise, these looks have defined a moment

YOUNG: I love Celine Dion, but I really hated [the backward-tux moment]. I hate a fedora so it’s really hard for me to get past it. [The suit] is actually quite chic, but the fedora and the sunglasses are too many.

KATZ: Celine Dion is such a certified style icon in 2021, but 20 years ago that wasn’t the case. People laughed at his madness and in 2021 it is celebrated, as it should be.

Lil ‘Kim’s Misa Hylton-designed jumpsuit instantly became one of the most recognizable looks of all time when the rapper walked the red carpet at the MTV Video Music Awards on September 9, 1999.

MISA HYLTON (stylist and designer): Missy Elliott actually gave me the idea for this look. One day, I was hanging out with her and she said, “You know what? Kim is such a fly slut. If I was Kim, do you know what I would do? I would only have one breast outside. So I just made a mental note. The next big event we had was the 1999 MTV Video Music Awards, [and] this idea Missy gave me was the inspiration for the jumpsuit. I wanted to make it really nice and pretty; feminine and affectionate and colorful. So I bought some Indian bridal fabric.

AMBROSE: For me, it was such a liberating moment for women. It was a Gloria Steinem moment. [Kim was] own her body and her breasts. [It made me think of] walking the streets in the 60s … topless women … big signs that said, “We are women, listen to us roar!”

GIVHAN: Looking back, it certainly looks like it was a forerunner of Rihanna wearing a dazzling fishnet dress at the CFDA Fashion Awards, and Beyoncé wearing essentially a sparkly scrim at the Costume Institute Gala; a whole slew of prominent women who wore dresses a hair’s breadth away from them being totally naked.

Despite a growing public appetite for everything celebrity-related, including what the stars wore, a number of major fashion houses were still reluctant or unwilling to work with them. As a result, Ambrose and Hylton continued to design custom looks for their clients, as did Tina Knowles-Lawson for Destiny’s Child.

YOUNG: Fashion and fame weren’t friends yet. Fashion has really stayed away; it was really snobbish at the time.

KATZ: Back then, the big fashion houses didn’t lend to people of color or bigger people. And it still exists today. There is a lot of discrimination when it comes to the way clothes are provided to celebrities.

AMBROSE: I didn’t have the luxury to take a look. [Design houses] wouldn’t even take my calls back then. So what are you supposed to do? You have to understand it.

KATZ: Tina Knowles-Lawson deserves her flowers. It is worth paying tribute to him for saying, “I don’t have the resources at my disposal to get what I want, so I will become a resource for this group myself.

HYLTON: By [2000] I had started to build relationships with [designers], because Lil ‘Kim was the hottest thing, and everyone wanted a piece of her. We sat in the front row of fashion shows, Donatella Versace took us to her home on Lake Como…. Now, if you go back a few years, it was very difficult.

AMBROSE: Design houses didn’t start talking to us until they saw the impact we were having on retail, consumers, and pop culture. We didn’t need to go back and have a conversation with them, but I thought it was important for inclusiveness that we all spoke together as one. And that’s why I was open to collaborating with and working with designers. Plus, they had a top seam and access that we didn’t have.

Soon the red carpets seemingly usurped the awards, with much of the talk surrounding fashion events.

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