Britney Spears’ best fashion moments through time.
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.
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.
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.
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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.
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.
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.
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.
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.