Oprah Outfits That Just Didn't Work For The Icon

Oprah has been on television for decades, so it's safe to say that her style has drastically changed over the years. Unfortunately, not all her choices are winners. The former daytime television host doesn't have one particular look, and fans have seen her in everything from billowing skirts to fitted tailored suits. Oprah's longtime stylist, Kelly Hurliman, reflected on the time the media mogul chose to wear a long plaid wool skirt on TV, telling Oprah.com. "I wasn't even going to show it to her because I knew plaid wool probably wouldn't look great on TV, but she saw it and loved it and said, 'Let's wear it on today's show.' And it wound up looking like a fringed sofa blanket," the stylist shared.

About her boss' clothing preferences, Hurliman told Oprah.com, "She gravitates toward clean lines and pieces that are soft and well-made. She's willing to try something new but isn't into trends — she knows what suits her." Fans of Oprah know that she loves dressing for comfort, but she'll definitely bring out the high-end designer duds for a good red carpet look, like the stunning purple Louis Vuitton dress she wore to the 2024 Golden Globes. However, some of the fashion risks she took fell flat or just weren't flattering at all. While she's had some good sartorial hits, the television icon has had a few misses as well.

Oprah's early 2000s style was all about showing off her curves, and she did just that at the 2002 Emmy Awards with a butter yellow corset dress. While the color looked gorgeous on her, the ruching at the bosom and sleeves made the gown look like a milkmaid costume instead of couture. The straps also looked like an unnecessary addition, and only made the top half of the dress look too busy. Perhaps she was just channeling her inner Belle from "Beauty and the Beast," but Oprah could have done with a more structured 'fit that night.

If you're invited to a royal wedding, this is the time to step it up in your chicest, most elegant outfit. Sadly, Oprah took the opportunity to attend Meghan Markle and Prince Harry's wedding in a blush pink layered dress with lace trimming that made her look like a doily. And while it's customary to wear a hat at royal weddings, Oprah's pick was way too over-the-top. From the wide brim to the feathered flowers, subtle was not the word to describe her headwear. The media mogul revealed in an Instagram video that the pink dress was a last-minute decision because her original beige choice would have looked white in pictures. While her second choice wasn't great, at least Oprah avoided being that celeb who showed up to a wedding in an inappropriate outfit.

In 2013, Oprah attended Beyoncé's "Life Is But a Dream" premiere wearing a navy blue jersey wrap dress. While wrap dresses typically look great on any body shape, Oprah's seemed a tad small, as indicated by her undergarment peeking out from one shoulder — a big fashion mistake.

The thin material clung to her arms in an unflattering way, and the hem, which fell just before her knees, shortened her legs. What's more, the broach was oddly placed and would have looked better pinned higher on the chest. If the dress were a size larger and had better styling, Oprah's red carpet 'fit would have been a winner.

Since starring in the 1985 film "The Color Purple," Oprah has worn various shades of the color over the years. Most of the time, she got it right, but she went way overboard during the lighting of the Empire State Building in December 2023. As she and the cast of the 2023 musical adaptation celebrated it's premiere, Oprah donned a lilac pants-and-shirt combo in a shiny satin finish. 

Oprah didn't just stop there — perched over her outfit was a glittery purple and yellow coat that shone brighter than a disco ball. Although glittery details took over in the winter of 2023, the outfit, combined with sparkly shoes, was just a clashing mess. Instead, Oprah should have chosen one stand-out piece and worn neutrals as a complement. We get that she wanted to dress on-theme, but head-to-toe purple was not the right choice.

Oprah has always loved a crisp white button-up, sharing on Oprah Daily, "Some people collect stamps; I collect white shirts." Unfortunately, she collected the wrong one with the oversized tunic version she wore to the Louis Vuitton Cruise fashion show in May 2023. 

The high-low style fell to her calves in the back, and paired with baggy white pants with blue stripes, the unstructured look did not flatter the media mogul at all. It looked like she attempted to tie the look together with a skinny belt, but the long dangling end just added to the messy look. For a high-end designer event, Oprah could have gone with a 'fit that didn't look like she just rolled out of bed.