Oprah Winfrey's 1986 Oscars Dress Scarred Her (& May Have Helped Shape Her Self-Love)

They say that beauty is pain, but Oprah Winfrey unfortunately experienced the reality behind that idiom at her very first Oscars. The year was 1986, and the popular talk show host was nominated for best actress in a supporting role for the period drama "The Color Purple." Only instead of her Academy Awards debut being a dream come true, it turned into a nightmare when her gown literally left her scarred (though it still didn't land her on our list of the worst-dressed celebs in Oscar history). 

Ron Galella

During an April 2026 appearance on "The Late Show with Stephen Colbert," Winfrey recounted how her gold-and-white dress, which featured a 12-pound intricate beaded collar, actually pulled at her skin. "I got a gown but I didn't know ... that you're supposed to get it fitted before you actually go to try to put it on," she explained to the host. "So when I went to sit back in the chair, [the beaded collar] choked me, and I ended up the night with a scar on my neck." Winfrey revealed that when she appeared to be clutching her chest, she was actually her trying to free herself of the collar that was choking her. "And you know, I heard the voice of God say to me, 'You're not gonna win ... 'cause you can't get out of the chair.' I wouldn't have been able to get out of the chair."

While this was a red carpet outfit that seriously hurt, it did leave the former talk show host with a powerful lesson. "After that, I decided no matter what you're doing, you want to be comfortable," she went on. "I don't do anything that's not comfortable now." Along with sticking exclusively to practical fashion, the media mogul has also learned a thing or two about pain and self-love.

A lifetime in the spotlight is bound to produce some scars, and Winfrey has accumulated a few during her decades in Hollywood. In addition to her Oscars injury, she ended up getting a double knee replacement in 2021 , a difficult procedure which left her with some noticeable marks on her legs. 

"Thanks to that surgery, I'm active, healthy, and able to fully inhabit my body without pain or limitations," she wrote on her website Oprah Daily in 2025. "And yet I have felt self-conscious about the scars on my knees. For four years now, I've covered them up so no one would see them." However, Winfrey soon realized that her scars didn't make her less lovable. The revelation came to her while deciding what to wear when filming in New York City a few years later. "I was about to change into pants, but then I thought, 'Why not!' I loved the outfit," she added. Winfrey appreciated the "new lease on life" the surgery gave her, and decided to embrace her knees, scars and all. "I have no reason to hide them," she said. "I'm proud of what they represent." In the end, she bared her knees to everyone in the studio and noted that "it felt good to bring them to light." 

Even now, Oprah Winfrey's complete transformation, from Weight Watchers to Ozempic, shows that despite embracing her scars, leg-baring 'fits aren't her preferred look. But still, Winfrey took the painful lesson she learned at the 1986 Oscars and pivoted to a kinder, comfort-forward mindset. Whether she's rocking an easy all-denim aesthetic or a roomy leather jumpsuit, she's no longer navigating outrageously heavy or restrictive looks. And more importantly, she flaunts her wardrobe with confidence.