Shania Twain’s wildest retro fashion and beauty moments | Gallery

Happy birthday, Shania Twain! The country music star turned 56 on Aug. 28, 2021. To mark the occasion, Wonderwall.com is taking a look back at the Canadian singer-songwriter’s wildest retro fashion and beauty moments from early in her career. Let’s start with this look… For her performance of “Man! I Feel Like A Woman” during the 1999 Grammy Awards, the Canadian singer rocked a corset top and a miniskirt with black tights, over-the-knee boots, opera gloves and a choker.

Keep reading to relive more of her most fantastically dated looks…

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During the 2003 American Music Awards, Shania Twain wore a wacky bondage-inspired dress featuring horizontal buckles from the neck down. The befuddling frock, which she wore with over-the-knee lace-up boots, also featured an asymmetrical skirt that ended in a tulle train. Now let’s take a closer look at her equally wild hairstyle…

During the 2003 American Music Awards, Shania Twain’s half-up hairdo had it all: a pouf, a combination of crimped and stick-straight strands flowing all the way down her back and a messy bun with tightly curled pieces sticking straight up.

During the 2001 American Music Awards, Shania Twain sported a white sleeveless jumpsuit with a plunging neckline over a shimmery bra top … and an insane amount of gold accessories: shoulder-skimming dangle earrings, a multi-strand necklace that hung way below her bellybutton, a lace-up belt featuring metallic fringe and platform heels. Next, check out her hair and makeup…

During the 2001 American Music Awards, Shania Twain rocked a pouf ‘do, sparkly peach lipstick, matching peach eyeshadow and chunky lashes.

Shania Twain chose a truly over-the-top ensemble for her performance during the 2003 Super Bowl halftime show: a shiny black open-front dress over a rhinestone-encrusted bra top and a black miniskirt adorned with bejeweled white straps. She completed her look with a statement choker, matching dangle earrings, fishnet tights and over-the-knee boots.

Shania Twain walked on the wild side during the 1999 ACM Awards. She wore a leopard-print coat dress that she untied later in the evening to reveal a simple black strapless column dress underneath.

Shania Twain was a vision in white during the 1999 Grammy Awards. She donned a sequined curve-hugging gown with a high collar and wore her hair in a chic bun to pick up two gramophone trophies for her hit single “You’re Still The One” — best country song and best female country vocal performance.

Shania Twain wore a teal cropped blazer over PVC separates — pants and a midriff-baring top — during the 1996 American Music Awards. (She won the award for favorite country new artist that night.) Check out her hair and makeup next…

Shania Twain reached new heights with her volumized ‘do during the 1996 American Music Awards. She completed her look with some quintessentially ’90s beauty trends: overlined lips and plenty of black eyeliner.

During the 1995 Billboard Music Awards, Shania Twain paired black lace-front pants with a midriff-baring turtleneck sweater. She wore matching red lipstick to complete her look.

Shania Twain rocked leopard print again during Z100’s Fourth Annual Jingle Ball at Madison Square Garden in New York City on Dec. 17, 1998. This time, she wore a black leather vest and matching leather pants over a sleeveless turtleneck crop top.

Shania Twain got her leopard-print sleeveless turtleneck crop top in two different colors! She rocked a lime version of her favorite top during a concert in Houston on Oct. 31, 1998. (If you look closely, you’ll see that her black pants featured a strip of fabric in the same green print!)

It was another turtleneck look for Shania Twain during the 1998 Billboard Music Awards. She wore a velvety cream gown with a tulle cape that connected to one of her rings, giving her an ethereal look as she collected the awards for top female artist and hot 100 singles artist. Keep reading to see her beauty look…

During the 1998 Billboard Music Awards, Shania Twain wore her long brunette locks in tight curls and topped off her look with a gold headband. She also rocked gold shades of lipstick and eyeshadow.

The following year during the 1999 Billboard Music Awards, Shania Twain rocked yet another gown with a turtleneck. This time, she donned a sleeveless cornflower blue column dress with an oversized keyhole cut-out. The country music superstar accessorized with a matching headband and an extra-long satiny stole that reached all the way to the floor.

Yep, more leopard print! Shania Twain wore a blazer in her preferred print while performing on the Nov. 7, 1997, episode of “The Tonight Show with Jay Leno.”

Shania Twain looked ready to rock in a one-shoulder black dress with an asymmetrical midriff cut-out and a thigh-high slit during the “VH1 Divas Live” concert in New York City on April 14, 1998. Now you need to see her hair!

During the “VH1 Divas Live” concert in New York City on April 14, 1998, Shania Twain wore her hair in a curled updo. Now it’s time to take a closer look at her makeup…

During the “VH1 Divas Live” concert in New York City on April 14, 1998, Shania Twain experimented with one of the hottest beauty trends of the ’90s: blue eyeshadow rimmed all the way around her peepers. She also sported pearl-and-diamond drop earrings.

During the 2002 CMA Awards, Shania Twain sparkled in a gold sequined column dress with an extra low-cut cowl neck that revealed part of her matching bra top.

Shania Twain gave us “Fran Drescher on ‘The Nanny'” vibes with her ensemble during the 1996 Blockbuster Music Awards. The country music singer wore a black leather jacket and pants over a white button-down and completed her look with a red scarf tied around her neck, matching red lipstick, dark eyeshadow and a hairdo with extra volume on the top.

You guessed it: More leopard print! During the 2003 CMT Flameworthy Awards, Shania Twain wore a billowy leopard-print blouse with khaki cargo pants, a pendant necklace and sandals.

If you look closely enough, you’ll see that the curve-hugging strapless dress with detached sleeves that Shania Twain wore to the 1998 Rock & Roll Hall of Fame Induction Ceremony featured leopard print. (Yes, again.) She wore her hair in loose curls and completed her looked with naturalistic makeup

Shania Twain delivered one of her wildest looks yet during an appearance on the “Today” show in November 2002. She wore a black leather floor-length coat over a turtleneck top featuring printed text across the bust that she tucked into bootcut jeans. She accessorized with a braided belt (so 2002!) and gloves.

Shania Twain wore a white mesh tee over a black bra top while performing during Capital FM’s Party in the Park in London’s Hyde Park on June 15, 1998.

Shania Twain paired a cropped black leather tank with bronze pants during the 1997 American Music Awards.

Shania Twain looked adorable in a denim-on-denim look — a vest over a white crop top with distressed light-wash jeans — while performing on “The Tonight Show with Jay Leno” in July 1995.

An absolutely stunning Shania Twain showed off her sporty side in a cropped football jersey, which she wore with low-rise jeans, in a promotional photo for her 1999 CBS concert special “Winter Break.”

Shania Twain had another fun fashion moment in a promotional photo for “Winter Break” — this time alongside Elton John, who made a special guest appearance on her 1999 CBS concert special. The country music star sported a sleeveless striped crop top with matching pants. She topped off her look with a coordinating mustard scrunchie.