Dolly Parton's Best-Dressed Awards Show Moments

Award-winning singer, songwriter, actor, and business mogul Dolly Parton is known for her maximalist approach to fashion. In fact, she has professed her love for the shinier things in life publicly. In 2019, Parton told Vogue that her outfit just doesn't feel complete if it doesn't look like a well-lit disco ball. "I always joke that I never leave a rhinestone unturned," she said. "I have to have sparkles on my clothes. It makes me feel vibrant. Shoot, even my pajamas have rhinestones on them!" Parton's iconic style evolution throughout her decades-long career shows that doesn't shy away from a bold and bedazzled look on the carpet — one of our favorite qualities about her.

The mastermind behind these epic red carpet moments? Parton's longtime stylist Steve Summers. The designer shared an inside look at how much work goes into curating the singer's larger-than-life wardrobe when he chatted with Vogue in 2023. "Even if she wears a dress that's off the rack, it doesn't look like it by the time she gets it on," Summers shared. "There's a customization that happens no matter what she's wearing. There is an outfit in production every single day. If she's doing personal appearances, 10 outfits in a day is not unusual." Many throwback pics of Dolly Parton prove she's always been an icon, and so do some of her best outfits at award show appearances.

Dolly Parton stunned at the 2023 Academy of Country Music Awards in this silver masterpiece. Complete with rhinestone fringe on the shoulder pads, bottom of the top, and pants, this uniquely tailored look totally stole the show. The cut of the pants is perfectly flattering and hits right at the ankle. Not many could pull off something dripping with such opulence, but Parton rocks it with ease. This outfit is very on-brand for her.

Dolly Parton wore this vibrant red number to the 2019 Grammy Awards.The frills and fringe are quintessentially Parton. Even in 2026, the star holds this outfit in high regard. She told the Country Music Hall of Fame and Museum that these red shoes hold beautiful memories. Parton liked red high heels as a child, and her love for them continued once she reached adulthood. "Every time I wear those shoes, I think of those little shoes [I loved as a kid] in that box of rags!" she said.

Dolly Parton arrived at the 2016 Academy of Country Music Awards  wearing a lavish cream mermaid-style gown fit for a member of the royal family. Now, while the royals stick to neutral color palettes most days, Parton wouldn't be caught dead without her signature bedazzlements, so she added them to the floor-length skirt. To complete the look, she wore extra-large diamond teardrop earrings and a bold, eye-catching ring.

Dolly Parton has always been known for her over-the-top style, and the look she wore to the 2001 Grammy Awards was no exception. This was one of Dolly Parton's biggest head-turning hair moments, so it was certainly hard to miss. Of course, Parton's white rhinestone off-the-shoulder dress was equally as head-turning. She even topped off the look with rhinestone-encrusted tights. That night, Parton performed in this look and took home the award for Best Bluegrass Album. It's safe to say the night was a big win for her on all fronts.

The beautiful sapphire blue number Dolly Parton wore during her performance at the Country Music Awards in 2003 really stands out among her many costume changes, even more than 20 years later. Parton can pull off any hue, really, but this rich shade of cobalt proved to be her color. She styled the look modestly, but it still featured Parton's signature sparkle around the sleeves and skirt. A nice touch that wasn't overly loud, but still felt true to her character.

Dolly Parton had, not one, not two, not three, but five costume changes during the Country Music Awards in 2019. While every piece she wore was iconic, this white fringe dress gave her an ethereal quality. About this presentation, she commented, "Everyone needs a little more light and love, and that's what I wanted the performance to be. I love sharing these beautiful, uplifting songs with the world!" she told Vogue on 2019.