Celine Dion's 1999 Oscars Look Wasn't A Fan Fave But She Got The Last Laugh

Celine Dion may be known for hits like "The Power of Love" and "My Heart Will Go On," but the singer has also made her mark on the red carpet. Dion is no stranger to wearing the spiciest, head-turning outfits imaginable, showing just how daring she can be with her fashion choices. And she has no issue with standing out, as seen with Dion's gorgeous hair transformation, but even more so when she showed up to the 1999 Oscars in a truly unconventional, yet eye-catching, get-up that served to cement her place in the annals of fashion history. 

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Although Celine Dion also made history with her powerful duet with Andrea Bocelli, fans would not soon forget her strange styling choice on the red carpet either. The "All By Myself" vocalist wore a white tailored suit combo straight from the racks of John Galliano's 1999 spring collection. But instead of wearing the blazer portion as normal, Dion wore it backwards, gifting fans to a backless moment. She paired the outfit with a white fedora hat and shades, while keeping her hair in a low ponytail. The outfit landed on many worst dressed lists, but the vocal powerhouse ignored the fashion critics and showed that she definitely knows her stuff when it comes to fashion. 

Celine Dion's decision to go with her gut and walk out onto the red carpet in that outfit back at the 1999 Oscars has undoubtedly paid off, so it's unsurprising that she doesn't regret the styling choice at all. In a segment of Vogue's "Life in Looks" series, Dion was asked about this specific moment. The five-time Grammy Award winner held nothing back as she detailed what went through her head as her stylist recommended wearing the blazer backwards. "I thought my stylist made a mistake by putting this outfit the other way around," Dion confessed. 

The mission was clearly to make sure that Dion stood out, as the pop star recounted that all the other women were in dresses. Although Dion had her reservations, she ultimately decided to go with her stylist's recommendation, and boy was it the right decision. "It's pretty gutsy. Fierce," Dion told Vogue. "Years passed and now it became ... something that people still talked about because I trusted my stylist." Dion echoed this sentiment in 2017, when she told People, "If I would do this today it would work. It was avant-garde at the time."