Beauty Is Pain: Oprah Winfrey Had An Awful Experience Wearing This Oscars Outfit

Oprah Winfrey became a household name thanks in large part to her eponymous talk show, which debuted in September 1986. It was a big year for her professionally; earlier that year, she went to the Oscars for the first time. Winfrey was paid shockingly little for "The Color Purple," but she earned herself a Best Supporting Actress nomination for her work. As anyone who has watched the Oscars knows, it's a night to wear your most iconic dress, so Winfrey got herself a beautiful white and gold gown to wear for the occasion.

Unfortunately, while Winfrey may live a lavish lifestyle now, it sounds like her relative naivety about dressing for an event like this left her literally scarred, as the gown's heavy collar left a permanent mark on Winfrey. On an April 2026 episode of "The Late Show with Stephen Colbert," Winfrey spoke about her Oscars dress and what went wrong. "I got a gown, but I didn't know, because it was the first time I'd ever done anything," she said. "I didn't know that you're supposed to get it fitted."

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Since it wasn't fit exactly to her dimensions, the collar was too tight, especially when she sat down. Considering it weighed 12 pounds, that caused a bit of a problem. The result? "I ended up the night with a scar on my neck," Winfrey explained.

Oprah Winfrey's longtime bestie, Gayle King, who she met while they were both young journalists in the 1970s, was by her side at the 1986 Oscars. As such, she saw the dress drama go down in real time, and she actually wrote about it. In an article for The Hollywood Reporter, King wrote, "The day before the Oscars she tried it on, and it was too big. So she asked the tailor to come and take it in. He then made it too small. And she discovered that an hour before the show."

When you see pictures of her from the event, she doesn't look like she's in distress; perhaps she should have won the acting award for being able to hide her pain so well. Apparently, Winfrey knew that she wouldn't be getting the Oscar. As she told Stephen Colbert, when Winfrey was in the audience at the Academy Awards, doing her best to simply breathe, she "heard the voice of God say to me, 'You're not going to win. You're not going to win.'" That may have been a blessing in disguise, since the fit of her dress would've made it pretty difficult to get out of her seat to accept the award.

After that painful moment, Winfrey confirmed to Colbert that her new rule when it came to fashion was "to be comfortable," even at a prestigious event like the Oscars. With that kind of experience, it's no wonder. Our guess is that she also added advance fittings to her list of fashion musts.