At only 18 years old, Britney Spears' first VMAs look wasn't just for the red carpet, but part of a performance that cemented the star as a pop icon well before she had the discography to back it up. TBH, I think that everyone already knew she was legendary from the first time they watched the "(Hit Me) Baby One More Time" video in 1998. I mean, who could have heard that song and doubted the potential of this pop star's talents?
But back to the VMAs, let's think to 1999: Spears was not only appearing at the MTV Video Music Awards for the first time, but performing at the ceremony, too. Her first hit single — the aforementioned "(Hit Me) Baby One More Time" — was one of the most talked-about songs and videos of the year. This was Spears' chance to prove herself a performer to the whole world on a pretty prestigious stage.
When faced with this kind of task, it arguably becomes crucial to choose the right outfit to accompany your brand. And although Spears stuck to her school girl theme for the set and the dancer ensembles of her first VMAs performance, the star decided to differentiate herself from the jailbait theme with a more adult and bang on-trend outfit for 1999 — and it was a low-rise, leather dream.
The outfit consisted of a shiny two-piece that featured what seemed to be Spears' favorite clothing trend of the time: Low-rise pants. Trimmed with silver and paired with sneakers, this outfit was oh-so-early-'00s before the millennium had even struck. It was a far cry from the all-denim ball gown Spears would rock with then-beau Justin Timberlake at the VMAs in 2001, only two years later.
In 1999, Timberlake was still a member of the highly successful boy band *NSYNC, and the band actually performed "(Hit Me) Baby One More Time" with Spears onstage at this iconic MTV Video Music Awards.
Instead of appearing like a clash of the titans, Spears and *NSYNC came together to give one of the best performances of the song yet, all the while Spears rocked one of her simplest outfits ever. It was a look so well-liked that it even made its way onto one of the (highly collectable) Britney Spears dolls.
This may have been Spears' first VMAs appearance and performance, but it was far from her last. Personally, I find it great to see how far the artist has come in career since. And who knows? Maybe one day we'll get a throwback from her via a return to this look.