Sheryl Crow's wonderfully retro and outdated early fashion moments

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In honor of Sheryl Crow’s 60th birthday on Feb. 11, 2022, Wonderwall.com is taking a look back at some of the most wonderfully retro and outdated fashion moments from early in the singer-songwriter’s career, starting with this sexy look… During the 1994 MTV Video Music Awards, the “If It Makes You Happy” chart-topper looked red-hot in a skin-tight tee, a black leather micro-miniskirt, fishnet tights and combat boots.

Keep reading for more of her best vintage looks…

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Sheryl Crow showed some skin in a tie-front crop top with bell sleeves and embroidered pants while performing during the 1994 H.O.R.D.E. Festival in Mountain View, California.

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Sheryl Crow donned a truly late-’90s all-black ensemble during the 1999 Grammys in Los Angeles: a midi-length pencil skirt with a front split, a satiny zip-up corset and a mostly unbuttoned button-down shrug.

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During the 1999 NetAid concert event, Sheryl Crow paired black leather pants — a wardrobe staple for the singer-songwriter at the time, as you’ll see! — with a loose-knit top with a cross-shaped modesty panel.

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Those boots! Sheryl Crow’s striped shoes were the focal point of the bizarre ensemble she donned during the 2000 Grammys in Los Angeles — a split-front micro-miniskirt with a sleeveless loose-flowing blouse that she wore cinched at the waist with a wide grommet belt.

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Sheryl Crow rocked a sheer leopard-print duster with furry lapels and cuffs during the 1997 Grammys in New York City. We especially love that her floor-length coverup featured a finger loop! (All the better to pose with.) Now check out the rest of her ensemble…

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Before she covered up with a leopard-print duster during the 1997 Grammys in New York City, Sheryl Crow’s full-coverage leopard-print briefs could be seen peeking out from under her sheer LBD. (She initially completed her look with a loose-knit cardigan — a ’90s staple!)

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The denim maxiskirt is one trend we’re more than happy to leave in the past! Sheryl Crow rocked the early ’00s staple with a matching denim jacket and a midriff-baring tie-dye camo tee at the 2000 premiere of “Hollow Man” in Los Angeles.

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We remember this trend! Sheryl Crow played with color during the 1997 premiere of “Tomorrow Never Dies” in London: She donned a red velvet duster with a blue faux fur collar.

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We undoubtedly have 1999’s “The Matrix” to thank for this look! The same year the sci-fi film debuted, Sheryl Crow rocked this Trinity-inspired ensemble — black leather pants, black boots and a black cardigan over a blue tee — while visiting the “Pepsi Chart” show studios in London.

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If you were alive during the ’90s, you’ll likely recall that the peasant-inspired aesthetic had a major moment. Take this look, for example! Sheryl Crow donned a white dress with bell sleeves, a lace-up neckline and a floral motif during the 1998 Grammys in New York City.

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Sheryl Crow rocked an all-red look — an open-back halter top with pants featuring a sequined floral motif — during a 1999 concert in New York City’s Central Park.

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Sheryl Crow sported black leather pants and a black tank while rocking out in Brussels on Valentine’s Day in 1999. She completed her look with royal-blue arm warmers.

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Sheryl Crow rocked this wild ensemble — a mostly unbuttoned blush button-down with loud gold printed pants — at a 2000 fundraising concert for then-presidential hopeful Al Gore.

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Sheryl Crow went full boho during the 1995 Grammys in Los Angeles: She wore a red jacket featuring a gold embroidered floral motif over a white knit top and black slacks.

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Sheryl Crow sported a loud orange suit with a minty button-down at an undisclosed 1997 ribbon-cutting ceremony.

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During the 2000 Vanity Fair Oscar Party in West Hollywood, Sheryl Crow paired a satiny maxiskirt with a spaghetti-strap top featuring sheer beaded panels. Our favorite part of her look, though? That would be her arm candy: then-boyfriend Owen Wilson.

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The ’90s brought back velvet in a major way! Sheryl Crow wore a crimson velvet vest — unbuttoned and sans undershirt, of course! — with jeans and a brown leather belt during a 1995 visit to the “Later with Jools Holland” studios in London, where she posed with fellow ’90s singer-songwriter PJ Harvey.

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During a 1994 concert in London, Sheryl Crow wore a cropped Felix the Cat tee with a colorful maxiskirt and a loose-fitting black leather jacket.

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During a launch party for Madonna’s “Music” album in 2000, Sheryl Crow wore an open-back brown leather halter top with olive boot-cut pants featuring a geometric pattern.

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Sheryl Crow rocked an oversized pinstriped suit at APLA’s 1995 Commitment to Life event in Los Angeles. She completed her look with one of the most popular accessories of the ’90s: an extra-long gothic cross pendant necklace.

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It was a brown suede suit sans undershirt for Sheryl Crow during the 1997 premiere of “The Game” in New York City.

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Sheryl Crow had another major coat moment during TNT’s “A Very Special Christmas” concert in Washington, D.C., in 2000. She wore a satiny black duster featuring a red embroidered floral motif and furry lapels.

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During the 2000 premiere of “What Lies Beneath” in Los Angeles, Sheryl Crow wore a truly bizarre sleeveless ruched top with jeans and heels.

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Back in 1996, Sheryl Crow wore a red-and-white patterned jacket over a midi-length LBD with red trim during the grand opening of a new Versace boutique in New York City.

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During a 1999 Versace party, Sheryl Crow sported a floor-skimming coat over leather pants and a loose-flowing white blouse.

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Celebs dressed very differently for award shows back in the day. Sheryl Crow, for example, chose a shapeless white sleeveless sheath for the 2000 People’s Choice Awards in Pasadena, California. Oddly, she completed her look with black accessories: chunky heels and a purse with a gold embroidered floral motif.

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Sheryl Crow chose a shapeless spaghetti-strap LBD that accentuated her toned arms for the 1997 APLA benefit gala in Los Angeles.

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Sheryl Crow modeled a relatively dressed-down look — a simple gold dress with coordinating sandals featuring a gold floral motif — during the 1996 VH1 Honors event in Los Angeles.

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During the 1997 VH1 Honors event in Los Angeles, Sheryl Crow paired velvety pants with a black illusion top featuring a floral motif and red lining at the neck and cuffs.

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