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Sheryl Crow's transformation in photos as she turns 63

The artist recently celebrated 30 years since her 1995 triple-Grammy win

Maria Sarabi
Junior Writer
February 11, 2025
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February has turned out to be a month of celebration for country singer Sheryl Crow. Last week, the musician graced the Grammys in a jaw-dropping strapless sequin chevron gown courtesy of Missoni. 

The sparkly silver number was adorned with colorful cascading embellishments in a zig-zag pattern. Hues of purple, blue and green glistened in the flashes of cameras, while the star's turquoise pendant necklace from Neil Lane jewelry added a statement of drama. 

Sheryl Crow stunned in Missoni© Getty Images
Sheryl Crow stunned in Missoni

Sheryl was celebrating 30 years since her 1995 triple-Grammy win for Best New Artist, Record of the Year, and Best Female Pop Vocal Performance. Later in the evening, the country hitmaker slipped into another glitzy number as she joined Dawes, John Legend, Brad Paisley, Brittany Howard, and St. Vincent on stage in a performance of I Love LA.

The dazzling look consisted of a silver mini chainmail two-piece courtesy of Naeem Khan layered over a black bralette and matching shorts. The sparkly number was teamed with knee-high blue Louboutin cowboy boots and a stack of diamond-encrusted bracelets. Sheryl's luscious blonde shoulder-length locks were styled into soft waves while her makeup oozed glamor with a smokey eye and a glossy lip.

Sheryl traded her gown for a glitzy mini-dress© Instagram
Sheryl traded her gown for a glitzy mini-dress

The 63-year-old has been curating an identifiable sartorial agenda throughout the years. From sporting her signature denim and cowboy boot combo to exuding high-fashion in coveted gowns, Sheryl has built up an archive of undeniably iconic looks. 

Sheryl Crow, Brittany Howard, and St. Vincent perform onstage during the 67th Annual Grammy Awards © Getty Images for The Recording A
Sheryl Crow, Brittany Howard, and St. Vincent perform onstage during the 67th Annual Grammy Awards

The Grammy winner discussed her fashion agenda with the Daily Mail back in 2018. She said: "Honestly, my style hasn’t changed that much [in 30 years]. I still gravitate towards comfy, fitted t-shirts, a great pair of jeans or a maxi dress and cowboy boots.

"On stage, it’s about comfort and cool for me because I move around a lot. I usually wear a great pair of tricked out jeans, a statement tee and a “wow” jacket paired with sneakers. Every day I just love wearing jeans and T-shirts paired with western boots. 

Sheryl in 2002© Getty Images
Sheryl in 2002

"It’s about creating unexpected combinations, like an embellished top with a pair of jeans or a really basic tank with a great pair of pants and a super unique topper. 

"My closet is filled with many vintage pieces I’ve collected over the years, so it’s also a lot fun to mix the old and the new."

To usher in Sheryl's 63rd birthday, HELLO! has delved into the archives to reveal the singer's major transformation. 

Sheryl Crow sported luscious curls© Getty Images

Grammys 1995

Sheryl looks almost unrecognizable in a photo taken at the 37th Annual Grammy Awards as she sported her signature auburn-toned curls with a burnt-red lip. The singer donned a dark red jacket adorned with green floral embroidery. The eye-catching garment was layered over a crochet white top.

The singer opted for a western-inspired look© Getty Images

Grammys 2002

The country star wowed in a western-inspired ensemble at the 44th Grammy Awards. The look featured a black playsuit adorned with a plunging neckline, a criss-cross tie detailing and a slew of daring cutouts. Sheryl teamed her figure-hugging look with a matching cowboy suit and a grey fluffy cape for an added element of drama. The singer's square-framed sunglasses are the epitome of Noughties nostalgia.

Sheryl Crow stunned in the silk number© Getty Images

Ethereal silk 2004

Sheryl was a vision in a champagne gown for the 2004 Costume Institute Gala 'Dangerous Liaison's at the Metropolitan Museum of Art. The look featured a strapless asymmetrical neckline embellished with a turquoise accent on the collarbone. The glossy garment boasted a daring thigh-high slit and was teamed with matching open-toe heels.

The metallic gown oozed chic© Getty Images

Chanel 2005

The American musician stunned in a metallic gown for the 2005 'Chanel' Costume Institute Gala opening at the Metropolitan Museum of Art. The dress featured a stylish sweetheart neckline with a ruby jewel embellished onto the bodice. The figure-hugging number boasted a fishtail silhouette with a mini train.

Sheryl strutted down the runway in red© Getty Images

Rouge 2006

Sheryl turned heads in a fiery scarlet gown as she graced the Heart Truth Red Dress runway during Olympus Fashion Week. The halterneck look was crafted from silk and oozed glamor.  

Sheryl in Ralph Lauren© Getty Images

Ralph Lauren 2018

In the last decade, the country star has become synonymous with Ralph Lauren's stylish tailoring. Sheryl Crow attended the Ralph Lauren 50th Anniversary event during New York Fashion Week. For the occasion, the singer donned a halterneck black velvet gown embellished with green and gold jewels on the bodice.

The singer opted for her signature jeans© Getty Images

Today Show 2022

The star sported her signature ensemble while appearing on the Today Show in 2022. Sheryl donned a black waistcoat adorned with floral prints and a pair of slim fit dark–wash jeans. The look was completed with a pair of brown boots with a chunky heel.

Sheryl Crow attended the Ralph Lauren fashion show© Getty Images

Ralph Lauren 2023

Sheryl added a western twist to her silky Ralph Lauren ensemble for their fashion show in 2023. The gown boasted a chic iridescent quality and was embellished with gold studs on the plunging neckline. Sheryl draped a brown leather jacket over her shoulders and teamed the grey number with a pair of camel-toned wedges.

The leather look featured stylish fringing© Getty Images

Leather ensemble 2024

The singer opted for an all-leather ensemble as she took to the stage during P!NK The Summer Carnival in 2024. The buttery black playsuit was adorned with tassel fringing for added cowgirl chic.

Sheryl opted for a sophisticated number© Getty Images

Suit ensemble 2024

Sheryl's ivory tailored number was a far cry away from her vintage leather jackets and figure-hugging jeans. The singer looked stunning as she attended Grammys On The Hill in 2024. The polished blazer was adorned with gold sequins on the collar and layered over a silky waistcoat.

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