Britney Spears’ Most Iconic Outfits

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With Oops… I Did It Again being the first album I’ve ever owned, Britney Spears’ outfits in performances and appearances have remained main memories in my childhood. Though everyone may not be as big of a Britney fan as I am, she was undoubtedly one of the most influential pop stars of the late ’90s and early ’00s.

Her debut studio album, …Baby One More Time, was released on January 12, 1999. It debuted at number one on the U.S. Billboard 200 and was certified two-times platinum by the Recording Industry Association of America after a month. Worldwide, the album topped the charts in fifteen countries and sold over 10 million copies in a year. It became the biggest selling album ever by a teenage artist.

Oops!… I Did It Again, her second studio album, was released in May 2000. It debuted at number one in the US, selling 1.3 million copies. This broke the SoundScan record for the highest debut sales by any solo artist.[36] The album sold over 20 million copies worldwide to date. It is one of the best-selling albums of all time.

Her iconic outfits only made her more incredible next to her amazing voice and killer dance moves.

Here is the Queen of Pop’s most iconic outfits that made my (and your) childhood.

“Slave For You” Performance

Image via Kevin Kane/ Wireimage

Not only did she perform effortlessly and beautifully with a snake around her neck. She did so in impeccable style, wearing a jewel-toned, green crop top and boy shorts with cape, with more than enough shimmer to go around. MTV VMAs in 2001

The Glam Biker Leather Look

Image via Henry McGee/ Globe Photos/ Alpha

As she wore a lace detailed skirt with a leather vest, mesh half sleeves,            strappy stilettos, and a cabbie hat, Spears pulled off the glamorous biker look perfectly. MTV VMAs in 2002

Pigtails and Midriff

Image via Getty/ Steve Grantz

Spears donned a pink leather tube top and matching patches on her white cargos. At the time this was the best mix of sexy and innocent that the world had seen. One More Time Tour in 1999

Sunny Day 

Image via Getty/ NBC

She matched a yellow leather jacket with yellow leather pants and just a white crop top underneath. It would take anyone, but her, a lot of confidence to rock this look. The Tonight Show with Jay Leno in 1999

Pop Royalty

Image via Getty/ Dave Hogan

She shows us the true pop princess that she is in this pastel, tulle, ballgown dream. Grammy’s in 2000


I tend to focus my attention outwards and am drawn to the external world of action. I learn a lot about the world through experience. Focusing on what I have seen, heard, or touched, gives me the ability to develop a practical and realistic outlook on the world. Making decisions based on impersonal criteria like principles and logic is very important to me.I accept responsibility for my actions. When I succeed, I accept the satisfaction of the achievement, and if I do fail at something, I learn from it and do better next time. I feel confident in my abilities and am accepting of myself. I have good time management skills. I am able to fit the most important things in life into my schedule. I have a strong sense of goal commitment.

  • Maya Asregadoo

    It’s fun to see some of these trends, like tube tops and suits, etc., coming back now!

  • Madeline LePage

    I think pop royalty is my favorite look on her!

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