So Nostalgic

24 Years Ago, Britney Spears Wore Her Most Revealing Outfit Of The '90s

My Roman Empire.

Originally Published: 
Britney Spears during The 1999 MTV Video Music Awards.
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Today’s fashion phenoms can’t stop reaching for sheer numbers. Gigi Hadid, Florence Pugh, and Megan Fox, are some of the countless see-through aficionados normalizing the barely-there look. Back in the ’90s, however, only the most daring of style stars dared traverse translucent ground.

One such icon, who was always ahead of her time, was Britney Spears.

One look, in particular, marked the dawn of her spicy era: a risqué see-through top that was out of the ordinary for her at the time.

Britney’s Very, Very Sheer ’Fit

Back in 1999, Spears had just released her debut album ...Baby One More Time, which instantly catapulted her to megastardom. While the video for her namesake single flaunted skin, by way of crop tops and minis, her style had more of a girl next door vibe at the time.

During this era of her style, the “Crazy” singer often donned pigtails and baby tees — her signature for most of the 1990s. Her appearance at the 1999 MTV Video Music Awards, however, changed that.

Before making her debut VMA performance in gunmetal co-ords, Spears walked the red carpet in an ultra revealing look that belongs in her wardrobe hall of fame. Spears wore a long, fur-trimmed cardigan that swept the floor. Despite having yards and yards of fabric, the garment was utterly see-through.

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Sans a bra, Spears’ only form of coverage was a smattering of sequins and two fur panels that strategically covered her breasts. She hooked one button and left the rest of the gauzy garment open, fully exposing her belly button.

She merchandised the all-black look with low-rise trousers (because ’90s) and sandals encrusted with crystals.

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Her Makeup Was Quintessentially ’90s

While Spears’ daring attire fits right into 2023’s spicy fashion trends, her makeup was so very ’90s.

She rocked frosted, baby blue eyeshadow with black eyeliner and dusted her entire face with shimmering bronzer.

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Oops!... She Did It Again

With the turn of the millennium, Spears’ style sensibilities pivoted to the spicier side — making her earlier look seem downright tame. Just a year later, Spears debuted another revealing sheer look, donning her first whale tail at the 2000 MTV VMAs (a monumental moment).

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It wouldn’t be ’til 2009, a decade after her first sheer ’fit, that she’d return to the see-through look. I’m talking about the barely-there masterpiece: her glistening “Toxic” bodysuit.

Screenshot via YouTube/BritneySpearsVEVO

Spears has always had a spicy streak. That 1999 look, however, was her gateway.

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