One More Time: Britney Spears’ Sexy, Strappy, See-Through Red Carpet Looks

It’s been 20 years since Britney Spears’ “Baby One More Time” album dropped.

While a lot of things have changed during that time span, one thing’s remained steady: Spears’ willingness to wear daring ensembles on the red carpet.

At the MTV Video Music Awards in 1999, Spears showed off her signature sultry-meets-sweet red carpet style. She wore a see-through duster with feather trim, going shirtless underneath. With feather trim narrowly preventing a wardrobe malfunction, the star completed her look with black pants and satin sandals.

Britney Spears wears a see-through duster with strappy sandals at the MTV Awards in September 1999.
CREDIT: Erik Pendzich/Shutterstock

Another daring look came at the MTV VMAs in 2001, two years later. At that event, Spears wore a see-through lace minidress that barely covered her upper thighs. She paired the sensual dress with strappy black low-heeled sandals.

Britney Spears wears a see-through lace minidress and kitten heels at the MTV Music Awards in September 2001.
CREDIT: Erik Pendzich/Shutterstock

The performer sang onstage in an even more daring look, draping a yellow snake around her shoulders as she performed “I’m a Slave 4 U” in a green bejeweled bikini.

Britney Spears
In 2001 for Britney Spears’s infamous “Slave 4 U” performance featuring a live Burmese Python, she dressed in an emerald bikini and custom knee-high boots.
CREDIT: FN Archives

That same year, Spears stepped out on the red carpet in an instantly iconic denim-on-denim look alongside then-boyfriend Justin Timberlake at the American Music Awards. The 37-year-old wore her strapless denim gown with a thick choker, while Timberlake complemented his Canadian tuxedo with a denim cowboy hat.

SPEARS TIMBERLAKE Show host Britney Spears, left, and Justin Timberlake of N'Sync arrive at the 28th Annual American Music Awards in Los Angeles. "Mad Men" star Jon Hamm is going mad over Justin Timberlake's suit and tie, the song and the singer's style. As for Timberlake, Hamm believes the pop star has "always been a very fashion forward kind of guy," except his all denim ensemble shown here that he wore to the 2001 American Music AwardsJon Hamm-Justin Timberlake, Los Angeles, USA
Britney Spears wearing a denim dress alongside Justin Timberlake at the 2001 American Music Awards.
CREDIT: Shutterstock

The 2001 AMAs weren’t the only time Spears went with a costume-like red carpet look. At the 2002 VMAs, she stepped out in a black minidress with a leather bodice and sheer paneling at the side. She completed her look with black pointy-toed pumps that featured straps going up to her knees.

Britney Spears VMA Style
In 2002, Britney Spears sports a leather ensemble with legwrap heels at the VMAs.
CREDIT: Shutterstock

In the 2010s, Spears continued to show off her toned body in daring red carpet looks.

At the 2016 Billboard Awards, she put a more modern update on her 2002 VMAs outfit, picking a see-through Reem Acra dress that revealed her underwear underneath. The “Toxic” singer paired the leg-baring dress with Schutz cage boots that went past her knees.

Britney SpearsBillboard Music Awards, Arrivals, Las Vegas, America - 22 May 2016WEARING REEM ACRA Billboard Music Awards
Britney Spears wears a see-through Reem Acra look with a soaring train at the Billboard Music Awards in May 2016.
CREDIT: Shutterstock

And in 2018, Britney Spears made a splash at the GLAAD Media Awards in an ultrashort, sparkly minidress, which she paired with see-through, pointy-toed pumps.

britney spears, glaad awards, minidress, christian louboutin pumps
Britney Spears wears a tiny dress with cut-out detailing on the 2018 GLAAD Awards red carpet.
CREDIT: Shutterstock

Click through the gallery for more of Britney Spears’ most daring red carpet looks.

Britney Spears Outshines All at the GLAAD Media Awards in the Tiniest, Sparkliest Dress

Britney Spears: A Look at Her Onstage Shoe Moments

Britney Spears’ Feet Slip Out of Her Sandals, but She Keeps on Walking

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