Oprah Winfrey to Kim Kardashian: How Bing Crosby inspired the ‘Canadian tuxedo’ as stars keep the trend alive

The Canadian tuxedo has been around since the 1950s and is still as trendy as ever.

Legend has it that the term Canadian tuxedo was born after Bing Crosby was denied entry to an upscale hotel in Vancouver, Canada for being underdressed, as he was wearing a denim on denim outfit designed by the popular jeans brand, Levi.

After hearing about Crosby's situation, Levi Strauss & Co. designed a full denim tuxedo for the singer, so he would never be accused of being underdressed again.

Since then, the denim on denim look has been dubbed the Canadian tuxedo and has been worn by countless celebrities, including Oprah Winfrey and Kim Kardashian, both on and off the red carpet.

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Here are some of the stars who have rocked a Canadian tuxedo

Oprah Winfrey was spotted waving at fans while out and about in New York City in a denim outfit.

The talk show host wore a pair of high-waisted jeans which flared out at the bottom, which she paired with a loose denim jacket with puffy sleeves and gold buttons.

She paired the look with dangling gold earrings, a pair of sunglasses and a brown purse, styling her brown hair in big curls.

Justin Timberlake and Britney Spears brought the Canadian tuxedo back into the mainstream when they posed for photos at the 2001 American Music Awards.

Spears wore a floorlength strapless denim dress, which she paired with a denim purse, a silver chain around her waist, and silver jewelry, including a statement necklace and bracelets.

Timberlake also wore head to toe denim, including a denim cowboy hat and jacket, which he paired with a pair of sunglasses and a silver necklace.

"It was such a no-brainer. Justin and Britney were dating at the time. We were in New Orleans when Britney and Justin were like, 'We're doing matching denim.' And I was like, 'How are you doing that? Who is doing that?'" designer Steven Gerstein told Jezebel in October 2022.

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"It was kind of like their prom," he added. "They had an idea, and we did what they wanted as opposed to the other way around...The rest is history."

Katy Perry brought a darker take to the denim on denim trend when she stepped out of her London hotel in 2024.

The "California Girls" singer was photographed leaving her hotel dressed in dark denim pants and a matching jacket, which she paired with black sunglasses and open-toed shoes.

This isn't the only time Perry has rocked the Canadian tuxedo, as she has been spotted sporting the look both on and off the red carpet in the past, even recreating Spears' iconic AMA moment.

"That moment Britney gave us was the moment, and I wanted to pay my respects," she said about her own denim red carpet moment at the 2014 VMAs.

Bella Hadid put her own spin on the denim on denim look, while out and about in Paris, France in 2020.

The supermodel was photographed in the city of love wearing baggy denim jeans, which she paired with an oversized fleece-lined denim trench coat with a brown crop top underneath, giving a hint of midriff.

She paired the look with black sunglasses and black square-toed shoes, and styled her long brown hair with two microbraids to frame her face.

Anne Hathaway had a denim moment when she posed for photos at the CFDA Fashion Awards in November 2023.

The "Princess Diaries" star turned heads on the red carpet in a floor length light-wash denim skirt with floral designs printed on throughout, which she paired with a darker strapless denim corset top with buttons going up the torso.

She paired the outfit with a soft makeup look and dazzling Bulgari jewelry, including a large statement necklace, bracelets and earrings.

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"In this moment, everybody's taking risks and I feel like there's more than one way to do it right now, which means that you don't have to hit a mark, you just have to be yourself — and that feels wonderful," Hathaway told People in 2023 about how her stylist, Erin Walsh, has made her comfortable taking risks with fashion.

Singer, Dua Lipa, brought a modern twist to the Canadian tuxedo when she was photographed for a day out in New York.

The singer stepped out in a denim bustier top which showed off her toned abs, which she paired with patterned jeans with built-in heels, combining two trends in one.

Dua Lipa accessorized the look with a matching denim purse, a low-slung belt and diamond jewels, including earrings, bracelets and a necklace.

Emily Ratajkowski stunned when she was spotted sporting a Canadian tuxedo while out and about in New York City.

The model was photographed in a pair of straight-legged high-waisted jeans, which she paired with a matching button-up collared denim shirt.

She accessorized with a woven brown belt to break up the denim, which matched her brown shoes.

Jennifer Lopez stunned in a denim look at a special screening for her movie, "Hustlers," in New York in 2019.

The actress and singer wore a pair of dark wash denim Balmain jeans with a folded waistline and a dropped crotch and cargo-style pockets, which she paired with a matching strapless top.

She accessorized the look with big hoop earrings, a diamond necklace and bracelets and clear high-heeled shoes. She styled her hair in a half-up-half-down look and sported a heavy makeup look with bold lashes.

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Kim Kardashian turned heads when she walked the red carpet at the WSJ Innovator Awards in November 2019 in a custom Burberry look.

The "Keeping Up with the Kardashians" star wore an off-the-shoulder denim corset top with puffy sleeves and boning on the torso, and a pair of jeans which transitioned into navy leather chaps.

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She paired the look with blue high-heeled boots which matched the navy chaps. Kardashian let the outfit do all the talking, keeping her accessories to a minimum and going for a more subdued makeup look.

Megan Fox added some sparkle to her version of the Canadian tuxedo.

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The "Teenage Mutant Ninja Turtles" star was photographed with her former fiancé, Machine Gun Kelly, while leaving "Jimmy Kimmel Live," in a pair of baggy ripped denim jeans, a glittery silver top and a jean jacket.

Katie Holmes is known for her effortlessly cool style, and her take on the Canadian tuxedo is no different.

When attending the Alice + Olivia fashion show in February 2024, the "Dawson's Creek" actress wore a pair of baggy jeans, with a denim button up in a slightly brighter shade of blue.

The "Batman Begins" star accessorized the denim look with a black undershirt, a cream jacket and hot pink shoes, as well as a simple gold chain and a white purse.