The 32-year-old pop star has grown up before our eyes, bursting on to the music scene following the release of her debut album ...Baby One More Time at the age of 17, which became the biggest-selling album ever by a teenage artist.
But even before Brit Brit became famous for that sexy school uniform, the pop star had already dipped her toes into the world of showbiz, appearing on the Mickey Mouse Club as a child with fellow stars Christina Aguilera, Justin Timberlake and Ryan Gosling.
And it's not just her hit songs and her killer dance moves that have kept the "I'm a Slave 4 U" singer in the spotlight, as Spears has also made headlines for her well-publicized personal struggles in addition to her fashion sense.
"There's a lot of celebrity's out in the audience they didn't tell me about, which I'm really really glad because I would've freaked out," the superstar adorably told E! News back in 1999 at the Teen Choice Awards while sporting colorful eye shadow and wispy bangs (how cute is teen Britney?!).
Just one year later, Spears was facing backlash as she entered into adulthood in the public eye, sporting sexier outfits on the red carpet as she released her second wildly-successful studio album Oops...I Did It Again.
But the criticism didn't stop Brit Brit from showing her true colors (and enviable figure!) to the world, as she continued to be the subject of every tabloid thanks, in part, to her highly-publicized relationship with Timberlake.
"I'm not really nervous right now, before my performance I'm sure I'll be a little nervous, but LL Cool J I'm hosting with him and he makes me feel really comfortable so it ought to be OK," she told E! News in 2001 at the American Music Awards where she and the "Suit & Tie" singer rocked matching denim-on-denim attire.
Soon after Britney shocked the world with her coming-of-age performance at the 2001 MTV Video Music Awards, where she sang in a barely-there ensemble with a python draped over her shoulders.
One year later, she landed her debut role in the film Crossroads before releasing her 2003 album In the Zone, wearing a belly-baring yellow tank top and a pair of embellished baggy jeans to the album signing.
Spears' released her fifth studio album Blackout in 2007, and while the iconic record was overshadowed by her personal struggles, Brit Brit pushed forward and came back better than ever.
She went on to drop her sixth and seventh studio albums, Circus and Femme Fatale, and most recently debuted her eighth studio album Britney Jean, which she's dubbed her "most personal" album yet.
Britney is currently preparing for her upcoming two-year residency in Las Vegas, which begins Dec. 27. at Planet Hollywood Resort and Casino, where she's sure to make headlines for her costumes, killer dance moves and always-fierce attitude.
So take a look back at Brit Brit's fashion flashback and be sure to tune in to E! News' exclusive two-hour movie event, I Am Britney Jean, airing this Sunday at 9/8c on E!
Have you bought your tickets to Vegas yet?!