Dolly Parton's Most Inappropriate Outfits That Only She Could Pull Off

Unique, legendary, unprecedented — these are just some of the words typically used to describe country music icon Dolly Parton and, more specifically, her style. Between all the rhinestones, cleavage, and towering platform heels, the singer's inimitable fashion sense is in a league of its own, and that kind of status naturally lends itself to a few inappropriate moments from time to time. "I think everybody should dress the way they want to, the way they will be comfortable," she opined during a 2025 interview with Harper's Bazaar. "There is nothing in this world worse — and I've done it — than having to go to some occasion wearing something that you're not comfortable in, that you're self-conscious in. It is such a personal choice choosing what you put on in the morning and that's why I don't think you should follow what other people are wearing. You don't have to go by any rules but your own." 

Parton is used to people hating on her over-the-top style, even revealing to The Guardian in 2023 that her grandfather used to physically punish the future star for her wardrobe choices. But the opinions of others have never stopped Parton from expressing herself, with the singer reasoning, "Sometimes there's just that part of you that's willing, if you want something bad enough, to go for it." In the past, the "Jolene" hitmaker has been spotted in a few outfits that felt a little out of place for the occasion, whether they were too raunchy for a PG event or simply not quite formal enough. But even when she gets conservative fingers wagging, the Grammy winner manages to pull off even her wildest looks, thanks to her unapologetic approach.

The dress that Dolly Parton donned for the California premiere of "Steel Magnolias," in 1989, had a lot going on, but we're certain the eyes of the world were drawn to one spot in particular. Was this much cleavage inappropriate for a dramedy film premiere, particularly when it looks like Parton used body makeup to emphasize her already impressive assets? Perhaps. But she's the queen of country, and she can do whatever she wants. Moreover, this may also be one of Dolly Parton's biggest hair moments that had heads turning, which is really saying something.

The words "dumb blonde" are controversial enough on their own, and without explaining the context, few other celebs would get away with wearing a shirt with that phrase emblazoned on it. But Dolly Parton isn't most stars and, in 1967, she reclaimed those harsh words with her hit song of the same name. So when she chose this glitzy top for the 2010 opening of her Trinkets and Treasures store in Nashville, no one batted an eyelid. On someone with a less beloved reputation, or in the age of social media even, this look probably would have ruffled some feathers though.

Somewhat surprisingly, one controversial outfit that did make Dolly Parton the target of backlash was the Dallas Cowboys cheerleader-inspired look she opted to perform in at a Thanksgiving game between the Cowboys and the Washington Commanders, in 2023. The public had plenty of ageist comments to throw at her, but we reckon the "9 to 5" hitmaker can pull off the cheerleader look in any season of life. The real controversy was Parton wearing one team's colors during the halftime show, rather than staying neutral and avoiding the wrath of half the crowd. For the record, though, the phrase "dress your age" deserves banishment from fashion discourse. 

Did Dolly Parton come straight from her regular 9 to 5 job as a secretary, to the 2007 Songwriters Hall of Fame Awards? That's what her mango-toned skirt suit was giving anyway. Thankfully, this somewhat underdressed look (by her standards, anyway) was saved just in the nick of time by the addition of some fun gold metallic detailing. We're giving Parton the benefit of the doubt this time and assuming she purposely went for an office-inspired 'fit to give her fellow songwriters a chance to shine in their formal garb. At least she put her own creative spin on corporate wear.

Over the years, Dolly Parton has become known for her bright, vibrant, and often highly revealing costumes. But back in 1976, before she really found her groove, the singer took to the stage at a country music festival in the U.K. wearing an outfit that was dangerously close to her own skin color. She's almost completely covered up but given that this set was body-hugging and worn at a time before cameras could really zoom in the way they can today, this was definitely a risky sartorial choice. But again, looking at the Dolly-esque rhinestones, all is forgiven.

Dolly Parton is no stranger to a thigh-high slit, but this white gown, which she donned on a 1970 red carpet, served us full-blown hip slit. The amount of leg on show for a black tie event (judging by the outfits of the folks around her) does lean towards slightly inappropriate territory, even with pantyhose underneath. If anybody else wore this, during a much more conservative time, there may have been calls for their head. But for Dolly Parton, this is just another notch in her belt of fabulous, boundary-pushing looks. Simply put, nobody does it like her.