Britney Spears has had some seriously memorable moments at the MTV Video Music Awards. From kissing Madonna to performing “I’m a Slave 4 U” with a live boa constrictor around her neck, the singer has owned the annual awards show many a time. Naturally, each of these crazy situations featured an equally wild ensemble. So as we prepare for the 2020 VMAs, we’re taking a look back at some of the “Toxic” songstress’ wildest and best looks of all time.
The singer attended the awards show for the first time in 1999. The then 18-year-old had three different looks over the course of the evening, all of which were a touch risqué but nothing like what she ultimately debuted in later years. She arrived on the red carpet in a sheer black coat with a fur lining, performed in a crop top and leather pants and wore something similar in the form of snakeskin pants with a bra when she was spotted backstage.
Pairing a bra with on-trend super low-rise fitted pants seemed to be a go-to for the “Baby One More Time” singer throughout the early 2000s. In 2007, Spears infamously performed “Gimme More” at the VMAs after a four-year hiatus. She took to the stage wearing a rhinestone bikini with fishnets and black mid-calf boots. The performance was questionable but the outfit was undeniably epic.
It hasn’t always been about her midriff, however. The blonde beauty also favored cute and playful minidresses, several of which were covered in eye-catching sparkles and/or sparkly sequin embellishments. But our favorite dress of all is the one she wore to the 32nd annual show in 2016. She stunned in an asymmetrical black number that featured a sexy sheer design that teased the star’s cleavage.
The moral of the story is that Spears is and will always be a VMA style queen. Join Us by scrolling to see the hitmaker’s wildest and best VMA looks of all time.