Britney Spears: Top 10 Most Iconic Looks

Hit us baby, one more time.

By Sowmya Krishnamurthy

Happy birthday Britney Spears! It’s hard to believe that the pop star is 34-years-old today. It’s been 16 years since the singer’s breakthrough debut …Baby One More Time took over airwaves and bedroom posters and became the best-selling album by a teenage solo artist.Britney was the Queen of Pop and everyone, including Madonna, wanted a piece of her. For nearly 20 years, Britney has given us midriff-baring fashion, barely-legal dance moves and pop anthems that will forever live on in our karaoke playlist. Here’s a look back at Britney Spears’ most iconic looks.

1. Oh baby, baby…


Britney Spears’ naughty schoolgirl look in the “…Baby One More Time” video inspired a generation of teenage dreams. Catholic school never looked so sexy.

2. Did I do that?

Britney always played a barely-legal sex symbol. In “Oops!...I Did It Again,” she clearly took this reputation with a wink and skin-tight bodysuit.

3. Britney and Justin

Before there was Jelena or Kyga, there was Britney and Justin. They didn’t have a cool celebrity name (Bustin?) but the former Musketeers-turned-pop stars were ridiculously cute when they dated. 

4. Young love

Even as Disney kids, Britney and Justin were adorable.

5. Frenemies

In the 90s, you were a Britney girl or a Christina Aguilera girl. The two met on the set of The Mickey Mouse Club and were always pitted against each other as solo artists. The frenemies united for this rare appearance on the 2000 MTV Video Music Awards. 

6. Cold-hearted snake

A true performer, Britney always committed to her live shows. When she hit the stage of the 2001 MTV Video Music Awards for “I’m A Slave 4 U,” she showed off her killer abs and a giant snake named Banana. 

7. Abs for days

Speaking of abs…Brit had us all doing extra crunches. 

8. Barbie girl

Britney always had a flair for drama. She showed off those The Mickey Mouse Club acting chops in Saturday Night Live byplaying Skipper to Amy Poehler’s Barbie.

9. Drink up

It’s cool to get your own Pepsi commercial. It’s even cooler to dress up like a Gladiator with Beyonce and Pink. 

10. Kiss me, you fool

Britney has been compared to Madonna since the start. In 2003, the Material Girl passed the pop torch—and her tongue—in this infamous MTV Video Music Awards kiss.

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