Dolly Parton Through the Years: A Look Back at the Superstar’s Most Iconic Moments

1976: U.K. Country Music Festival

Making her British debut at the U.K. Country Music Festival in London, Parton paired skin-tight pant suit with sky-high hair for an absolutely glamorous performance. Well known for believing “the higher the hair, the closer to heaven” Parton is absolutely in her element here, with artfully stacked curls and wispy bangs that frame her face.

Dazzling in pale pink, beading fans in an aura around the neckline and down her arms, drawing your eye up. For her first time in the UK, Parton absolutely floored with this rock glam look.

1978: Playboy Cover

Somehow worn by Keanue Reeve’s for Halloween later that same year, this iconic bunny look was one of Parton’s all-time best.

32 at the time, Parton was the first country music star to appear on the cover of Playboy, though she pointedly did not appear nude. Her interview was an honest and bold look into her personal philosophy, opening the interview by preempting the first question: “Hi. I’ll save you the trouble of askin’: Why do I choose to look so outrageous?”

Her answer reveals exactly why she’s been a fashion icon for so long. “It’s fun for me,” Parton says. “It’s like a little kid playing with her paints and colors. I like to sit and tease my hair. If there’s something new on the market in make-up, I like to try it.”

1980: 9 to 5 Premier

Making her silver screen debut, Parton’s role in 9 to 5 changed the game for her. In 2020, she told Vogue that the premier was intimidating. “I got to dress up like I was a city girl in this [film] and I’ve never even thought about being fashionable, I just always wore things that fit me,” Parton says. “But I thought, for something as big as a premiere, I needed to be fancy and I didn’t know how to do that.”

The Ann Roth gown, shown here with attendee and friend Jane Fonda, was a vision in pink pink satin and lace.

“I thought it was a beautiful dress,” Parton says. “I remember feeling really pretty, and I felt like I was well-dressed and not half-assed like sometimes you are. And I just remember that was probably the first time I ever really felt like I was fashionable.”

1984: Promo Shoot for Rhinestone

In her next big-screen move, Parton starred as a beleaguered country singer tasked with fixing up New York cabbie, Sylvester Stallone, into a bonafide country crooner. The promo shoot for the film, featured in Country Music Magazine shows Parton’s touch of glamour even in a more laid back denim look.

Charming and understated in a red lip and cowboy hat, there are still those tell-tale sparkles on her collar. Red plaid and high-waisted jeans will never ever go out of style, and this look proves that.

1987: Performing on Dolly!

It’s entirely possible that Parton broke a record here for the most pearls ever on a gown. Just look at gorgeous, delicate luxury. The high collar like dozens of stacked pearl necklaces and that iconic pearl fringe? This look should always be on a list of Parton’s best.

She looks nothing short of expensive, despite her long history of “looking cheap.”

1988: Promo Shot for The Dolly Show

Hosting her own variety show on ABC was no easy feat, but Parton looks like effortless elegance in this all-sequined look. The ’80s were notorious for their shoulder pads, but Parton has always been able to balance out her proportions to create the most glam and drama.

While the show only lasted one season, Parton still had a good time. “I managed to enjoy it,” she remarked to Interview Magazine in 1989. “I decided to do the most with the parts that were workin’ and enjoy that, and not to let it drive me crazy. I loved the clothes, I loved the guests that we had, I loved to get the chance to meet people, I loved the chance just to do it. And I learned a lot—what to do and what not to do. I don’t think the show hurt my career.”

1996: Performing on The Tonight Show

This is Dolly Parton’s version of understated. Perfecting the mid-90s straight half-ponytail, Parton stuns in this all black look for The Tonight Show. Her red lip and nails are the perfect spark of color in her otherwise all-black look. Usually one to play with color, it’s rare to see Parton in a fully black dress, and of course she looks incredible in it.

There’s something so romantic and soft about this look; it steps away from some of the more outlandish and sparkly styles Parton is known for. Maybe that’s why this look is almost always on round ups of her best fashion moments.

2006: The Oscars

For her second Academy Award Nomination for Best Original Song, the first being for 9 to 5 in 1981, Parton stunned in this light pink, intricate gown.

The song, “Travelin’ Thru,” was written specifically for the film, which is about a transwoman and her son. In press materials for the film’s soundtrack, Parton says, “It’s a remarkable movie that touches you in every single place of human emotion.”

Around this time, Parton’s sky-high hair saw another transformation into a piecey, feathered style that brushed her shoulders. Most importantly, it retains a lot of volume, even if it isn’t as close to heaven as it used to be.

2016: ACM Awards

No stranger to the ACM Awards, Parton has often taken the stage to perform during the ceremony. This time, she absolutely killed it in a bedazzled pantsuit.

Playing with shine and color, her blazer was a sweet nod to her song Coat of Many Colors, which was released back in 1971. The off-white trousers pair perfectly with her statement jacket, and we can’t get over the bedazzled tie!

2022: 37th Annual Rock & Roll Hall Of Fame Induction Ceremony

Just in case you thought Parton was slowing down now that she’s in her late 70s, her performance at the Rock & Roll Hall of Fame and the leather jumpsuit she wore should set you straight.

“I figure, if I’m going to be inducted into the Rock & Roll Hall of Fame, I’m gonna have to earn it,” Parton says before launching into Rockin’, which she wrote just for the occasion.

Her look, complete with big jewels and gold chains, perfectly encapsulates what we love about Dolly Parton: She’ll never stop having fun with her looks.