WWD Report Card: Free Britney

Britney Spears’ best fashion moments through time.


Britney Spears in Munich, 1999. Fryderyk Gabowicz/AP

With “…Baby One More Time,” this post-“Mickey Mouse Club” star shot late-’90s trends like these red textured pants, crop long-sleeved see-through top and ultra flat sneakers into the spotlight.


Britney Spears at the MTV Music Awards, 2002. Stephen Trupp/AP

At the MTV Video Music Awards in 2002, Spears turned heads with this leather S&M-inspired number accessorized with leather cap and lace-up pumps. Her softer side shone through with the lace inset and see-through gloves — and girl-next-door glam and innocent smile.


Britney Spears at the Versace Spring 2003 runway show in Milan. Giannoni Giannoni/WWD

Milan still remembers when Britney Spears sat in the front row at the Versace show in 2002 — and we do, too. With that asymmetric body-hugging, shimmery dress, she joined the ranks of Madonna and Jennifer Lopez while expanding her high fashion range.


Britney Spears poses during the MTV Video Music Awards, 2003. Hubert Boesl/AP

In what would become one of her most memorable performances, Spears channeled Madonna’s 1984 “Like a Virgin” performance flawlessly at the 2003 VMAs, including her sexy bridal look and oversize cross necklace and pearls. An outfit fit for showstopping.


Britney Spears, 2016. PA/AP


A cut out here, a slit there: this black playful look commands attention in a very calculated way. The covered sleeve really balances the exposed moments, showing maturity and a clear understanding of fashion’s power.


Britney Spears, 2016. The Mega Agency

Those Starbucks runs were iconic celebrity fashion moments in the mid-Aughts. Spears’ signature pink tank top, denim mini skirt and thong sandals are a delightful blast from the past. At the time, the look felt too casual, but the joke’s on us: this is a timeless jewel.


Britney Spears and Justin Timberlake American Music Awards in Los Angeles, 2001. MARK J. TERRILL/AP

This look was, of course, part of a couple’s denim-on-denim outfit that made fashion history but looking at her on her own, her solo effort, as always, shines. Britney deserved freedom then, as she does now.

Britney Spears performs with a snake during the finale of the 2001 MTV Video Music Awards. BETH A. KEISER/AP

Is there a more powerful Britney moment? The green bikini top, super low-riding hot shorts with sheer back skirt — and albino python snake — is all she needed for one of the most iconic stage looks of all time. No one does it like Britney.

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