Ever since Christina Aguilera first burst onto the scene with “Genie in a Bottle” in 1999, the pop star has been delivering one memorable fashion moment after another. Remember her leather chaps in “Dirrty,” or the glamorous burlesquewear she rocked in the “Lady Marmalade” video? Iconic! With a range of bold ensembles over the years, Aguilera was the perfect star to revisit some of her best outfits in a brand new Vogue Life in Looks video.

Aguilera’s reflections began with a look back on some of her favorite albums. In 1999, she made her debut with a self-titled record—a moment when she was still trying to figure out what her own style and tastes were. “I didn’t have any mobility to have a say yet, so I played it safe,” she says.

With 2002’s Stripped, however, Aguilera says she really came into her own—both with the music and her more sexy, free-spirited look. “I wanted this album to embrace every different part of being a woman,” Aguilera says. “There’s such a rulebook that’s handed to us [as women in music], and I was given it since I was a little girl. The older I got, the more I realized you have to stand up against it and create your own story. I wanted to go against the grain of what a pop star should look and sound like.”

She attributes some of her best red carpet ensembles to working with costume designer Trish Summerville in the early aughts (she’s responsible for the leather chaps Aguilera wore during her “Dirrty” era). “I was starting to be out of my shell a little bit… That was me coming into expressing who I was,” says Aguilera of the period. One of her favorites was the slinky metallic Versace dress she wore to the 2000 Grammy Awards. “I remember the metal vividly being so heavy,” she says. “It’s been so beautiful seeing other incredible women down the line owning this dress and giving it a new vision.” (Naomi Campbell, for one, has also worn the dress.)

Other highlights throughout Aguilera’s career? One was working on the “Lady Marmalade” video for Moulin Rouge with Pink, Mya, and Lil’ Kim. “That was one of my favorite moments of my career,” she says. “I loved working with these girls and seeing what they’re doing now.” She also looks back fondly on her 2007 Back to Basics era, when she toyed with more of an Old Hollywood look and sound inspired by greats such as Billie Holiday and Ella Fitzgerald. “These were the makers and creators of jazz, blues, and soul music that truly inspired me from a young age,” Aguilera says. “I went nowhere without a red lip at the time!”