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No matter what style you choose, wearing a black dress is always a good idea

He wanted to make sure she was ready for such a commitment

Her sexy, belly-baring schoolgirl uniform in the video for "Baby One More Time" paved the way for the low-slung jeans, navel rings, miniskirts, and bedazzled tank tops that would characterize the end of the decade's style

Sarah Carpenter, Bill Perlman and Janelle Lopez Genzink Director: Sam Wrench Showrunner: Nikki Boella Special Guests: Chappell Roan, Tyla, Shania Twain, Kali Uchis, Quinta Brunson, Cara Delevingne, Kyle Mooney, Nico Hiraga, Megan Stalter, Sean Astin, Owen Thiele and Jillian Bell