1990
A then-22-year-old Dion showed off her fashion range in high-waisted patchwork jeans and black leather cowboy boots. She surrounded herself with Louis Vuitton luggage to top off the look, as one does.
1993

Serving up a major ’90s moment, the singer wore a floral maxi dress, a long black shawl, and a choker to the premiere of Sleepless in Seattle.
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1993

Trying out the opposite side of the ’90s style spectrum, the singer channeled her inner bombshell in a red cut-out Versace gown at the American Music Awards.
1993

An early adoptee of the naked dress, she wore a sheer black gown with nothing but a black thong underneath to the 1993 Grammys. In true ’90s fashion, she accessorized the look with a black choker.
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1997

Going for another naked dress moment, Dion wore a sheer textured gown and nude underwear at the 1997 Grammy Awards.
1997

In a red-hot look, the singer donned a sparkling red gown that featured a sheer panel over her stomach.
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1997

In a taupe one-shouldered gown and matching purse at an event.
1998

While out in Québec, the singer looked incredibly chic in a white suit and crop top. She accessorized the look with a matching Chanel bag and pearl earrings.
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1999

In a mix of high-low fashion, Dion styled a T-shirt with a ball gown skirt at the 1999 People’s Choice Awards.
1999

She wore a pale blue gown with sparkling asymmetrical detailing to the 1999 Grammys, where she took home two awards for the Titanic soundtrack.
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1999

In one of her most iconic looks of all time, Dion showed up to the ’99 Academy Awards wearing a white tuxedo blazer backward. The unforgettable John Galliano look was topped off with a hat and black rectangular sunglasses.
2003

During the decade of low-rise jeans and perma-exposed hip bones, the singer hit the red carpet in a cutout gown at the Billboard Music Awards.
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2006

She wore a silky white jumpsuit and scarf while attending a fashion show in Las Vegas.
2007

For the finale of her first Las Vegas residency, she stunned in an icy blue ruffled gown.
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2011

In a sparkling white gown and massive emerald and diamond necklace at the Academy Awards.
2013

In a white fur jacket and black leather pants while out in Paris.
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2015

Going for the shine factor, she returned to her Las Vegas residency in a sparkling metallic full-length gown.
2015

In a green leather mini dress and strappy sandals at the 2015 Billboard Music Awards.
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2016

In a black leather high-slit gown while out in New York.
2016

In a Vetements sweatshirt (fittingly emblazoned with a Titanic graphic), jeans, and gold heels leaving the Royal Monceau hotel.
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