01of 15Jeannie C. Riley, 1968Bill Preston/The TennesseanAt the second-ever CMA Awards (and the first to be televised) the “Harper Valley P.T.A.” singer Jeannie C. Riley walked away with the award for Single of the Year — and wowed with her swinging sixties go-go boots and ruffled mini combo.
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Jeannie C. Riley, 1968
Bill Preston/The Tennessean
At the second-ever CMA Awards (and the first to be televised) the “Harper Valley P.T.A.” singer Jeannie C. Riley walked away with the award for Single of the Year — and wowed with her swinging sixties go-go boots and ruffled mini combo.
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Johnny Cash, 1969
Banner Newspaper Archive/Nashville Public Library
03of 15Glen Campbell, 1973Banner Newspaper Archive/Nashville Public LibraryIt was still two years before the singer would become a “Rhinestone Cowboy,” but two-time hostGlen Campbellwore a studded suit that was clearly a sign of things to come.
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Glen Campbell, 1973
It was still two years before the singer would become a “Rhinestone Cowboy,” but two-time hostGlen Campbellwore a studded suit that was clearly a sign of things to come.
04of 15Willie Nelson, 1976Banner Newspaper Archive/Nashville Public LibraryLeave it to a “Red Headed Stranger” and his outlaw kin to take a sartorial swing at the black-tie affair.Willie Nelsonaccepted awards for hisWanted! The Outlawscollaboration withWaylon Jennings(who boycotted the show) in his now-iconic bandana and jeans. “I knew it was a little bit different than what they were normally used to at the CMAs, but I also felt like there were enough people out there that would be glad to see somebody go up there and dress down a little bit, dress more like the audience,” Nelson told Deborah Evans Price inThe CMA Awards Vault.
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Willie Nelson, 1976
Leave it to a “Red Headed Stranger” and his outlaw kin to take a sartorial swing at the black-tie affair.Willie Nelsonaccepted awards for hisWanted! The Outlawscollaboration withWaylon Jennings(who boycotted the show) in his now-iconic bandana and jeans. “I knew it was a little bit different than what they were normally used to at the CMAs, but I also felt like there were enough people out there that would be glad to see somebody go up there and dress down a little bit, dress more like the audience,” Nelson told Deborah Evans Price inThe CMA Awards Vault.
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Dolly Parton, 1978
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Barbara Mandrell, 1981
07of 15Trisha Yearwood, 1991"‘She’s in Love with the Boy’ had just come out but I wasn’t eligible to be nominated for anything. But I had a hit record and I was asked to perform on the show so I was really excited and nervous,“Trisha Yearwoodtold PEOPLE. " And I wore these pants — god bless everyone who said not to! — I was kind of like MC Hammer meets I don’t know what. It was a fashion mistake. But I was so nervous. And so shy.” And in the end, no fashion faux pas could ruin a night that included discovering a bouquet of flowers in her dressing room from Reba McEntire, with a card reading, “Welcome to your first CMAs.”
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Trisha Yearwood, 1991
“‘She’s in Love with the Boy’ had just come out but I wasn’t eligible to be nominated for anything. But I had a hit record and I was asked to perform on the show so I was really excited and nervous,“Trisha Yearwoodtold PEOPLE. " And I wore these pants — god bless everyone who said not to! — I was kind of like MC Hammer meets I don’t know what. It was a fashion mistake. But I was so nervous. And so shy.” And in the end, no fashion faux pas could ruin a night that included discovering a bouquet of flowers in her dressing room from Reba McEntire, with a card reading, “Welcome to your first CMAs.”
08of 15Billy Ray Cyrus, 1992Dean DixonBilly Ray Cyrus' massive hit “Achy Breaky Heart” took home the Single of the Year award, but we suspect his sleeveless fashion statement was not as big a winner with the country crowd that night.
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Billy Ray Cyrus, 1992
Dean Dixon
Billy Ray Cyrus' massive hit “Achy Breaky Heart” took home the Single of the Year award, but we suspect his sleeveless fashion statement was not as big a winner with the country crowd that night.
09of 15Reba McEntire, 1993Beth Gwinn/Retna Ltd.Reba McEntirewas a tomboy as a kid “and I had hand-me-downs all my life,” the star told PEOPLE. “So to have brand-new clothes that are sparkly? Sparkle and shine all day long!” Her most remembered outfit,thatred dress as it became known, elicited a gasp from the audience — and a query from her dad back home. “My daddy said later on, ‘Did you have that thing on backwards?’ "
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Reba McEntire, 1993
Beth Gwinn/Retna Ltd.
Reba McEntirewas a tomboy as a kid “and I had hand-me-downs all my life,” the star told PEOPLE. “So to have brand-new clothes that are sparkly? Sparkle and shine all day long!” Her most remembered outfit,thatred dress as it became known, elicited a gasp from the audience — and a query from her dad back home. “My daddy said later on, ‘Did you have that thing on backwards?’ "
10of 15Shania Twain, 1999Mark Humphrey/APThe 1999 Entertainer of the Year winner pushed the country envelope with her outfits as much as her pop stylings. From catsuits to midriff-baring crop tops,Shania Twainmade an impression, particularly on a new kid in town. “I actually worked for the CMAs as an intern when I first moved to town and escorting Shania Twain from stage after she performed back to the bus was a pretty surreal experience for me,“Dierks Bentleytold PEOPLE. “I don’t remember what she performed but I do remember a lot of black leather going on!”
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Shania Twain, 1999
Mark Humphrey/AP
The 1999 Entertainer of the Year winner pushed the country envelope with her outfits as much as her pop stylings. From catsuits to midriff-baring crop tops,Shania Twainmade an impression, particularly on a new kid in town. “I actually worked for the CMAs as an intern when I first moved to town and escorting Shania Twain from stage after she performed back to the bus was a pretty surreal experience for me,“Dierks Bentleytold PEOPLE. “I don’t remember what she performed but I do remember a lot of black leather going on!”
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Keith Urban, 2001
TAMMIE ARROYO
12of 15Taylor Swift, 2007Michael Loccisano/FilmMagic"The highlight of my senior year,” was howTaylor Swiftdescribed her first CMA win, the Horizon Award for new artists. So it was fitting that the teen donned a prom-worthy gown for the event. With a fitted corset bodice and a princess-style ballgown skirt, the silk taffeta dress was a style that Swift embraced repeatedly in her first years in the spotlight.
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Taylor Swift, 2007
Michael Loccisano/FilmMagic
“The highlight of my senior year,” was howTaylor Swiftdescribed her first CMA win, the Horizon Award for new artists. So it was fitting that the teen donned a prom-worthy gown for the event. With a fitted corset bodice and a princess-style ballgown skirt, the silk taffeta dress was a style that Swift embraced repeatedly in her first years in the spotlight.
13of 15Kacey Musgraves, 2014Rick Diamond/GettyIt was the best of nights, it was the worst of nights forKacey Musgraveswhen she performed with her hero,Loretta Lynn. “We both had our sparkly dresses on and Loretta was beyond sweet and welcoming. We talked about everything from fried chicken to tanning beds — she has one in her house!” Musgraves told PEOPLE. “We sang, ‘You’re Looking at Country’ and it was the best thing ever.” Except forone small detail: “My underwear came off right before right the performance! News flash: don’t wear stick-on underwear with a short dress. They peeled off right before the curtain opened. I didn’t know what to do but I ripped them off and I threw them to the side and I had to go commando for this performance and hope and pray to the Lord Jesus that there wasn’t an angle that was going to expose my secret! If you go back and watch, you’ll notice that I’m very knock-kneed. But I made it through and nobody saw.”
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Kacey Musgraves, 2014
Rick Diamond/Getty
It was the best of nights, it was the worst of nights forKacey Musgraveswhen she performed with her hero,Loretta Lynn. “We both had our sparkly dresses on and Loretta was beyond sweet and welcoming. We talked about everything from fried chicken to tanning beds — she has one in her house!” Musgraves told PEOPLE. “We sang, ‘You’re Looking at Country’ and it was the best thing ever.” Except forone small detail: “My underwear came off right before right the performance! News flash: don’t wear stick-on underwear with a short dress. They peeled off right before the curtain opened. I didn’t know what to do but I ripped them off and I threw them to the side and I had to go commando for this performance and hope and pray to the Lord Jesus that there wasn’t an angle that was going to expose my secret! If you go back and watch, you’ll notice that I’m very knock-kneed. But I made it through and nobody saw.”
14of 15Miranda Lambert, 2015Frank Micelotta/PictureGroupWhen you’ve won the Female Vocalist award a record-breaking six times in a row, you’ve earned the right to wear anything you damn well please when you scoop up your trophy, soMiranda Lambertopted to pick up her hardware in her performance outfit: a bedazzled T-shirt emblazoned withChris Stapleton’s name. “I had it custom-made that day,” Lambert told PEOPLE of the shirt that she kept on, fan-girl style, in Stapleton’s honor as he performeda show-stopping medley that night with Justin Timberlake. “Instead of putting on my next gown after I performed, I just wore it. His performance was something I’ll never forget.”
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Miranda Lambert, 2015
Frank Micelotta/PictureGroup
When you’ve won the Female Vocalist award a record-breaking six times in a row, you’ve earned the right to wear anything you damn well please when you scoop up your trophy, soMiranda Lambertopted to pick up her hardware in her performance outfit: a bedazzled T-shirt emblazoned withChris Stapleton’s name. “I had it custom-made that day,” Lambert told PEOPLE of the shirt that she kept on, fan-girl style, in Stapleton’s honor as he performeda show-stopping medley that night with Justin Timberlake. “Instead of putting on my next gown after I performed, I just wore it. His performance was something I’ll never forget.”
15of 15Carrie Underwood, 2018Image Group LA/ABCIn her landmark 11th year co-hosting withBrad Paisley, a pregnantCarrie Underwoodperformed her single “Love Wins” while wearing a cerulean Stello gown featuring a dramatic cape (with a subtle tie dye design on the underside!) and front cut-out. She tied the whole look together with smoky and shimmery blue eye shadow and Jared Lehr blue-green stone earrings.
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Carrie Underwood, 2018
Image Group LA/ABC
In her landmark 11th year co-hosting withBrad Paisley, a pregnantCarrie Underwoodperformed her single “Love Wins” while wearing a cerulean Stello gown featuring a dramatic cape (with a subtle tie dye design on the underside!) and front cut-out. She tied the whole look together with smoky and shimmery blue eye shadow and Jared Lehr blue-green stone earrings.
source: people.com
