Britney Spears, born December 2, 1981, is an undeniable pop music icon. She became a worldwide phenomenon in the late 1990s and continued to release hit after hit through the 2000s.
While her music career was unstoppable, Britney was dealing with a lot in her personal life. Mental health struggles lead to her conservatorship in 2008. The agreement left most of her personal decisions in the hands of her father, Jamie Spears.
She was released from the arrangement in late 2021 and has been happier than ever. In June 2022, she married longtime love Sam Asghari.
Britney’s had so many amazing moments over the years. Here, she looked too cute while attending the Arthur Ashe Kids’ Day at the U.S. Open in Sept. 1999. She was the picture of innocence in her glasses, pigtails and tennis outfit at the event.
Click through the gallery to see her various looks throughout her days in the business!