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Jeannie C. Riley, 1968
At the second-ever CMAs (and the first to be televised) the "Harper Valley P.T.A." singer 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
The Man in Black added a little flair to his throwback tux — white ruffles and tails! — and owned the night by scooping up five awards, including Album of the Year for Johnny Cash at San Quentin Prison and Entertainer of the Year.
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Glen Campbell, 1973
It was still two years before the singer would become a "Rhinestone Cowboy," but two-time host Campbell wore a studded suit that was clearly a sign of things to come.
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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. Nelson accepted awards for his Wanted! The Outlaws collaboration with Waylon 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 in The CMA Awards Vault.
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Dolly Parton, 1978
Parton began her career as the "girl singer" on the The Porter Wagoner Show and shared her first three awards with Wagoner, but by the mid-'70s she had come into her own as a solo artist —and a style standout. But neither her bombshell wigs and or her curvy figure could overshadow her musical talent.
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Barbara Mandrell, 1981
Mandrell, a musical dynamo who toured with Patsy Cline when she was only 13, owned the early '80s in country music and was the first to take home the CMA's Entertainer of the Year prize twice. A three-time CMA Awards host (from 1980-82), Mandrell admits her wardrobe changes didn't quite equal Carrie Underwood's double-digit gown count, but she was all about the glamour nonetheless. "It's a very special night, so I think one should dress very special," Mandrell, whose mother made her first CMA gown, tells PEOPLE. "That effort needs to be made. I remember through the years, I'd see some people who did not dress accordingly and I remember being disappointed by that. I'd think, 'This is the CMA Awards, come on!' It's about paying honor not only to the CMA but to your fellow performers."
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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 tells 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, with a card reading, "Welcome to your first CMAs."
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Billy Ray Cyrus, 1992
Billy Ray's 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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Reba McIntire, 1993
A four-time female vocalist of the year winner, Reba was a tomboy as a kid "and I had hand-me-downs all my life," the star tells PEOPLE. "So to have brand-new clothes that are sparkly? Sparkle and shine all day long!" Her most remembered outfit, that red 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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Shania Twain, 1999
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 made 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 Bentley tells 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
When the Australian transplant earned his first nomination for the Horizon Award, "I was very excited and I went to Manuel to have a suit made 'cause it was a massive occasion," Keith tells PEOPLE of the white embroidered jacket and trousers created by legendary Nashville designer Manuel Cuevas. "I wanted to really have something special so I had this suit made that had all these lyrics on it, and it was very special. And I ended up winning that night, which was absolutely mind blowing to me."
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Taylor Swift, 2007
"The highlight of my senior year," was how Taylor described 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 Taylor embraced repeatedly in her first years in the spotlight.
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Kacey Musgraves, 2014
It was the best of nights, it was the worst of nights for Kacey when 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!" Kacey tells PEOPLE. "We sang, 'You're Looking at Country' and it was the best thing ever." Except for one 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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Miranda Lambert, 2015
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, so Miranda opted to pick up her hardware in her performance outfit: a bedazzled T-shirt emblazoned with Chris Stapleton's name. "I had it custom-made that day," Miranda tells PEOPLE of the shirt that she kept on, fan-girl style, in Stapleton's honor as he performed a 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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On Sale Now!
For even more insider scoop from the CMAs -- which turn 50 this year! -- pick up People's Special Edition 50 Years of the CMA Awards, on sale now. And check back Wednesday night for all the best moments from the show!