Out Of All Oprah Winfrey's Wacky Outfits, This Is By Far Her Worst

Oprah Winfrey has had her share of fashion missteps over the years, but her attempt at channeling menswear at a Hollywood soirée might just take the top spot. The celebrated talk show host attended a star-studded dinner hosted by designer Brunello Cucinelli at Chateau Marmont in Los Angeles on December 5, 2024. She was photographed wearing a Brunello Cucinelli beige coat over a tan shirt and feather-embellished skirt, paired with a matching tie. She accessorized the look with her signature eyeglasses, black boots, and a white clutch, while keeping her hair and makeup clean and understated. 

Though we totally appreciate Winfrey's willingness to experiment with other styles, sometimes it's wise to play it safe and stick to a fashion formula that works. For this particular outfit, the color choice isn't flattering and makes Winfrey look dull and older. It also lacks the wow factor that she usually brings to the red carpet. 

In contrast, the Emmy-winning producer (whose net worth is even higher than you might realize!) was a total showstopper at last year's event in a white lace dress that was more her look. Over the years, we've seen Winfrey play with different outfits (and sometimes miss) as she slowly developed her signature style. In August 2024, just a few months before her disastrous menswear attempt, Winfrey showed her support for Vice President Kamala Harris by gracing the Democratic National Convention. In what is hands-down one of her best looks, she sported a purple suit that exuded power and complemented her complexion beautifully. At the GLAAD Media Awards in March 2024, Winfrey received the honorary Vanguard Award in a stunning black and purple dress that commanded attention. Regardless of her (many) fashion fails, Winfrey sure knows how to dress to impress. 

Even a style icon like Oprah Winfrey isn't immune to fashion disasters. Looking back at some of her fashion hits and misses, stylist Kelly Hurliman and creative director Adam Glassman talked about Winfrey's style evolution and what it's like working with the legendary host behind the scenes. "It's never been a relationship where I say, 'You're wearing this today,'" Hurliman said in the chat published on Oprah.com. "Oprah knows what she likes, she knows her body. At the end of the day, what she's wearing always comes down to what she wants to wear." Meanwhile, Glassman praised Winfrey's eye for fashion: "Oprah rarely goes shopping, but when she does, she always finds something that works." (Apparently, that's one way Winfrey spends her billions.)

Of course, based on her outfit at the Brunello Cucinelli dinner, Winfrey doesn't always nail it with her fashion choices. She's certainly worn some questionable looks in the past, such as her unflattering ensemble at the Los Angeles premiere of "Exhibiting Forgiveness" in September 2024 (pictured above). While we get the vision, Winfrey's oversized jacket and pants came off as sloppy rather than fashion-forward and sophisticated. 

In 2019, she also stumbled with her plain white dress at the Hollywood premiere of "David Makes Man," which she executive produced. And who could forget her infamous 1986 Oscars look, which didn't quite work out as she'd hoped? "I don't think Oprah uses clothes as a way of drawing attention to herself," publicist Kelly Cutrone told The New York Post in 2013. "She's usually very monochromatic and pulled together — she's better off understated."