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LeAnn Rimes got her start in the music industry at the tender age of 13 years old, and received her first Grammy a year later for her country hit “Blue.” As a youngster growing up in the 90s, Rimes had some questionable fashion choices on the red carpet, which is simply part of growing up. Her style has changed remarkably since the early days of her music career. 

LeAnn Rimes made history with her first-ever Grammy win in 1997, just a year after signing with Nashville label Curb. At only 14 years old, Rimes easily won both awards for Best New Artist and Best Female Country Vocal Performance for “Blue,” making her the youngest Grammy Award winner in history. 

LeAnn Rimes’ Red Carpet Style Today

(Kathy Hutchins/Shutterstock.com)

Interestingly, the recording of “Blue” that gained acclaim was a version Rimes recorded when she was only 11 years old, which makes her 1997 Grammy win all that more remarkable. Obviously Rimes’ earlier appearances on the red carpet happened when she was still a young teen.

So, we won’t judge her too harshly for wearing styles popular in the late 90s. That being said, we won’t waste an opportunity to point out those old trends, which Rimes both set and followed.

Bedazzling By Any Other Name

(Kathy Hutchins/Shutterstock.com)

The first red carpet style we feel is more of a flop came in 2014. Rimes and her husband Eddie Cibrian attended the Annual Trans4m Benefit Concert and to mark the occasion, both dressed their best. Cibrian looked handsome and cool in his jeans and gray vest combination, but we’re not so crazy about Rimes’ dress for one very specific reason. 

We absolutely hated the era where costume jewelry came attached to clothing, whether it’s a blouse from the mostly defunct Fashion Bug to a faux leather dress like this one. We love the way Rimes looks in this dress, but we just cannot support non-removable jewelry. Sorry, not sorry.

This Top Gave Us Warlike Flashbacks

(DFree/Shutterstock.com)

Our second red carpet flop came during Rimes’ marriage to Dean Sheremet, whom she infamously divorced in order to marry Cibrian. The two were still newlyweds when this photo was taken at the 2003 world premiere of Bruce Almighty. For this date night, Rimes went casual with a green striped V-neck blouse and a pair of blue jeans. 

Those who didn’t live during this era probably won’t recognize this shirt, but let us assure you that it had a stranglehold on colleges, high schools, and middle schools across the country. We’re glad we’ve finally moved on from this style of shirt, as well as the jeans, which are no doubt low risers with button enclosures that have absolutely no mercy on anything other than the flattest of stomachs.

Night Of the Extensions

(Everett Collection/Shutterstock.com)

In 2000, at the New York premiere of Coyote Ugly which featured Rimes’ singing talents as well as a brief cameo, Rimes was the consummate child of Y2K. The eye-popping orange and pink eyeshadow with zero blending was a testament to the times, but the true sin here was the hair extensions. Just like with the eyeshadow, no attempt was made to blend Rimes’ natural hair with the blonde extensions someone tacked on haphazardly. Somehow, the fake hair makes Rimes’ real locks look like cheap Barbie hair. A look where no one wins. 

Baby Doll, Baby Don’t

(Featureflash Photo Agency/Shutterstock.com)

A year earlier, at the 1999 WB Radio Music Awards, Rimes’ hair looked much more natural without all the extensions holding it down. The 90s were all about innocence (think Britney Spears in the “Baby One More Time” music video) and grunge. 

Rimes mixes the two themes of the decade together in this red carpet appearance, though we’re not all that crazy about the results. The baby doll t-shirt looks sweet against the black leather pants Rimes wears, but we can’t help feeling this outfit is missing that extra oomph, and we’re going to blame it all on her lackluster top.  

Our First Looks At LeAnn Rimes

American singer and songwriter LeAnn Rimes wins at the Billboard Music Awards at the MGM Grand in Las Vegas, 8th December 1997. (Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images)

Finally, we’ve come to two of LeAnn Rimes’ first red carpet walks. First up is Rimes’ 1997 victory lap after winning at the Billboard Music Awards, taking home four trophies for Artist of the Year, Country Artist of the Year, Country Singles Artist of the Year. She also picked up Album of the Year for Blue.

NEW YORK, UNITED STATES: LeAnn Rimes holds up her two Grammy Awards 26 February in New York. Rimes won for best female country singer and best women’s vocal new artist. (ELECTRONIC IMAGE) AFP PHOTO/Jon LEVY (Photo credit should read JON LEVY/AFP via Getty Images)

Last, but not least, is the first time many fans ever saw Rimes. The then 14-year-old had just made Grammy history as the youngest person to ever win an award, though Beyonce’s oldest daughter Blue Ivy recently broke that record. It’s amazing to think that Rimes literally grew up right before our very eyes. It’s only natural that she’d have some fashion fails along the way. Haven’t we all?

Holly Hunter’s Early Red Carpet Looks Predicted These Fashion Trends, And One Huge No-No

Emily Blunt’s First Red Carpet Featured Controversial Trend We’re Happy Is Over

Taraji P. Henson’s Outfit Choice During First Red Carpet Is A ’00s Catastrophe

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