Oprah Winfrey has spent more than four decades attending some of the most glamorous events in entertainment, so she knows exactly what an unforgiving red-carpet outfit can feel like.
These days, though, the 72-year-old media icon seems increasingly interested in something else: comfort.
That became particularly obvious as photos of Oprah in a loose, striped matching set circulated online. The relaxed silhouette immediately divided viewers. Some loved the effortless look. Others compared the flowing button-down and wide trousers to “pajamas” and couldn’t quite believe that one of television’s most powerful women would choose something so casual-looking for a high-profile appearance.
But Oprah’s fashion choices make considerably more sense when you know what happened to her the very first time she attended the Academy Awards.
Her glamorous dress that night was so uncomfortable that it actually left her with a scar. (Glam)
Oprah has been embracing a much more relaxed style
The “pajama” comparison isn’t entirely surprising.
Over the past year, Oprah has repeatedly appeared in coordinated sets, wide-leg trousers, soft tailoring and other pieces that combine polish with the kind of comfort normally associated with loungewear.
In August 2026, she was photographed in a lightweight striped top with roomy jeans, prompting fashion coverage of her increasingly relaxed approach to dressing. (People.com)
Earlier in the year, Travel + Leisure highlighted the wide-leg pants Oprah had selected for her Favorite Things list, noting her own description of them as both “chic and comfortable.” (Travel + Leisure)
And that isn’t an accidental combination of words.
Comfort has become something of a fashion philosophy for Oprah.
The reason goes all the way back to the 1986 Oscars
In 1986, Oprah was preparing for one of the biggest nights of her young career.
Steven Spielberg’s The Color Purple had transformed her from an increasingly recognizable television personality into an Oscar-nominated actress. Her performance as Sofia earned her a nomination for Best Supporting Actress.
It should have been a magical night.
Instead, Oprah recently revealed that her dress became a nightmare.
During an April 2026 appearance on The Late Show with Stephen Colbert, she looked back at the gold-and-white gown she wore to that first Academy Awards ceremony.
The outfit featured an enormous, heavily embellished collar.
According to Oprah, it weighed approximately 12 pounds. (Glam)
And there was another problem.
She hadn’t realized the dress needed to be properly fitted before the ceremony.
When she sat back in her seat, the heavy collar pulled against her neck.
Oprah said it effectively began choking her.
By the end of the evening, the pressure had left a scar on her neck — one she said she still has. (Glam)
She even wondered what would happen if she won
There was something almost comical about Oprah’s predicament — although it certainly wasn’t funny to her at the time.
Sitting in the audience as a first-time Oscar nominee, she realized she might have another problem.
What if they called her name?
The dress was so restrictive that she wasn’t sure she could simply leap from her chair and walk to the stage.
Looking back four decades later, Oprah joked that she heard the “voice of God” telling her she wasn’t going to win because she couldn’t get out of the chair anyway. (Glam)
She ultimately lost the Supporting Actress Oscar to Anjelica Huston for Prizzi’s Honor.
But Oprah walked away from the ceremony with something that influenced the way she would dress for years afterward.
“After that, I decided no matter what you’re doing, you want to be comfortable,” she explained. (Glam)
Suddenly, those “pajamas” make a lot more sense.
Four decades later, she doesn’t appear interested in suffering for fashion
Oprah can certainly still do full Hollywood glamour.
She has worn dramatic ball gowns, sequined dresses, sculptural eveningwear and designer couture over the decades.
But she’s equally willing to choose something loose.
That was particularly evident during Paris Fashion Week in March 2026.
After staying away from the Paris shows for approximately seven years, Oprah suddenly became one of the season’s most visible front-row guests.
She attended Stella McCartney, Chloé, Zimmermann and Chanel within a matter of days. (Marie Claire)
And rather than treating every appearance like an awards-show red carpet, she experimented.
At Stella McCartney, she wore an airy coral blazer over a crisp white shirt with enormous balloon-like cargo trousers.
At Chloé, she paired flared jeans with a cropped jacket.
At Chanel, she returned to classic black and white with a coordinated set and two-tone shoes. (Marie Claire)
Her stylist says Oprah is having fun with clothes again
There’s another reason her wardrobe has become more adventurous.
Oprah’s hairstylist Nicole Mangrum has said that recent lifestyle changes helped the media mogul begin “having fun with fashion” again.
Mangrum described Oprah going shopping and then returning to put on her own little fashion show. (Marie Claire)
That playful approach is visible in her recent appearances.
One day she looks classically Chanel.
Another day she is in giant cargo pants.
Then she’ll wear denim and Western-inspired Schiaparelli.
At the Cannes Lions festival in June, for example, Oprah wore Schiaparelli’s Western-inspired Cowboy Pants with hammered gold-tone details and an ecru silk top. (Essence)
At 72, she seems considerably less interested in following one rigid formula for what a woman of her age is “supposed” to wear.
And yes, Oprah genuinely loves pajamas
The funniest part of the online comparison is that Oprah actually has a long-established love affair with luxurious pajamas.
They have repeatedly appeared on her famous Favorite Things lists.
One Cozy Earth striped set impressed her enough that Oprah said she would buy the pajamas in every available color if she could. (Oprah Daily)
She praised the striped sets again as exceptionally comfortable, and the brand has remained closely associated with her annual recommendations.
So when viewers look at one of Oprah’s relaxed striped outfits and immediately think “pajamas,” they may inadvertently be landing on an aesthetic she genuinely enjoys.
The difference is that modern loungewear has increasingly blurred the old boundary between clothes meant for bed and clothes meant to be seen.
Wide trousers, oversized shirts and matching sets can now move between home, travel and public appearances with very little alteration.
Oprah seems perfectly happy living in that overlap.
Her appearance has changed dramatically in recent years, too
Clothes aren’t the only reason Oprah’s recent photographs have attracted attention.
Her physical transformation has been equally visible.
For decades, Oprah spoke publicly about her weight in a way few other celebrities did. Millions watched her lose weight, regain it, try new programs and discuss the emotional consequences on television.
Eventually, she reached a very different conclusion.
In 2023, Oprah revealed that she had incorporated a prescription weight-management medication into a broader approach that also included regular exercise and dietary changes.
She did not initially name the specific medication.
She explained that after years of treating weight as a question of willpower, having a medically approved tool felt like a “gift” rather than something she needed to hide.
She also described becoming significantly more active after knee surgery, eventually hiking three to five miles on many days and tackling longer hikes on weekends.
The result has been a visibly slimmer Oprah — and an entirely new era of fashion experimentation.
Yet the public still has strong opinions about what she wears
That part hasn’t changed.
When you’ve been famous for as long as Oprah, almost every outfit becomes an invitation for commentary.
Some people prefer her in traditional gowns.
Others love the newer tailored trousers and matching sets.
And inevitably, when an outfit is deliberately loose or sleepwear-inspired, somebody will ask why a billionaire showed up “in pajamas.”
But the criticism arguably reveals how much red-carpet expectations have changed.
Hollywood traditionally trained audiences to expect women to arrive cinched, sculpted and uncomfortable.
Oprah has personally experienced the extreme version of that expectation.
She literally has a scar from it.
At 72, she’s earned the right to decide that a waistband and a soft shirt might be more appealing than another 12-pound collar.
She can still turn on old-school glamour when she wants to
Comfort doesn’t mean Oprah has abandoned dramatic fashion.
Her recent Paris Fashion Week appearances proved the opposite.
At Chanel, she wore an elegant winter-white look accented with black tweed, cream-and-black heels and a quilted handbag. (Parade)
At Stella McCartney, she played with exaggerated proportions.
At Chloé, she went bohemian.
And her Cannes appearance added Western elements to the mix.
The common thread isn’t a particular silhouette.
It’s that Oprah increasingly appears to wear clothes she can actually move in.
The “pajama” comments may be missing the best part of the story
Put Oprah’s 1986 and 2026 wardrobes beside one another and the contrast is almost perfect.
At 32, she attended her first Oscars wearing a gown that looked suitably spectacular but physically hurt her badly enough to leave a lasting scar.
Forty years later, she can walk into an event wearing loose striped trousers and a flowing top while strangers wonder whether she accidentally forgot to change out of her pajamas.
Oprah probably understands the trade-off better than anyone.
She has done the painful gown.
She has done the restrictive couture.
She has done the towering heels and the elaborate red carpets.
And now she also does wide-leg pants, soft matching sets and clothes that occasionally resemble something she could happily wear at home.
That doesn’t mean everyone has to love every outfit.
Fashion is subjective, and the relaxed striped look clearly isn’t for everyone.
But Oprah herself gave the best explanation for it years before these particular photographs started circulating.
After an Oscar dress literally injured her, she made herself a promise: whatever she was doing, she wanted to be comfortable. (Glam)
Four decades later, she appears to be keeping it.
If you’re curious about other ways to feel your best, check out these tips on 7 Signs of a Vitamin D Drought or perhaps you’d like to give your gut some love with this 3-Day Carrot Recipe for a Lighter, Happier Gut.
