The Most Outrageous Outfit in Oprah Winfrey’s Fashion Journey

Oprah Winfrey has certainly had her share of fashion blunders, and one of the most notable was her attempt at menswear at a lavish Hollywood event. This occurred during a dinner hosted by designer Brunello Cucinelli at Chateau Marmont in Los Angeles on December 5, 2024. Winfrey was seen in a beige coat paired with a tan top and a feathered skirt, complemented by a matching tie. She completed this look with her iconic eyeglasses, black boots, and a white clutch, opting for a simplistic hairstyle and makeup.

While we admire Winfrey’s adventurous spirit in fashion, some occasions call for a more classic approach. Unfortunately, this specific outfit seemed unflattering, giving Winfrey a washed-out appearance and lacking her usual striking presence on the red carpet.

In contrast, Winfrey had a stunning moment during last year’s event, where she wowed everyone in a white lace dress that perfectly suited her style. Over the years, she has experimented with various looks, gradually honing her signature fashion sense. Just a few months prior to the menswear misstep in August 2024, Winfrey made a powerful statement at the Democratic National Convention in a stunning purple suit that accentuated her features beautifully. At the GLAAD Media Awards in March 2024, she captured attention wearing a breathtaking black and purple dress, which celebrated her evolving style. Despite a few misjudged outfits, Winfrey undoubtedly knows how to make an impression.

Despite being a fashion icon, Oprah Winfrey has faced her share of style setbacks. Fashion experts Kelly Hurliman and Adam Glassman explored her fashion evolution and what it’s like to work with Winfrey behind the scenes. According to Hurliman, their approach has never pressured Winfrey into specific outfits. “Oprah knows her own style and what flatters her,” Hurliman noted in a discussion shared on Oprah.com. Meanwhile, Glassman praised Winfrey’s unique fashion instincts, emphasizing that her rare shopping trips often result in great finds.

However, as highlighted by her attire at the Cucinelli dinner, Winfrey doesn’t always hit the mark with her clothing choices. She has had her fair share of unflattering outfits in the past, such as a less than stellar look at the Los Angeles premiere of “Exhibiting Forgiveness” in September 2024. Though the designer vision was present, her oversized jacket and pants ensemble came off as disheveled rather than chic.

In 2019, she also encountered challenges with a basic white dress at the premiere of “David Makes Man,” which she produced. Additionally, her polarizing look at the 1986 Oscars is often remembered as a misfire. As publicist Kelly Cutrone noted, “Oprah doesn’t use clothes to garner attention; her style is typically minimalistic and sophisticated.”