Oprah Winfrey made a small but meaningful purchase when she felt like she truly arrived at her big moment of success.
The media mogul had a nostalgic moment of reflection after attending Ralph Lauren’s intimate runway show on Wednesday, Sept. 10, at the designer’s Madison Avenue studio in New York City.
Back in 1986, when Winfrey was just beginning to establish her career as a television personality, she made what would become an unforgettable purchase.
“When I first started making enough money to actually be able to pay my rent and have some money left over my first big splurge was Ralph Lauren towels,” she said during an interview with The Associated Press.
“The Color Purple” star continued, “And so when Barbara Walters came to my house for the very first Barbara Walters interview at the end of the day, ‘I said, ‘Do you want to see my Ralph Lauren towels?’”
This wasn’t just about luxury linens — it represented a milestone moment when she could finally afford something beautiful beyond basic necessities.
Winfrey recalled how proud she was of this purchase that symbolized her growing success.
For the young broadcaster, Lauren represented “the standard, not just for dressing, but for home life and for what it meant to be surrounded by beauty and excellence.”
The story resonated deeply with fans when shared on social media, with many relating to that first meaningful purchase after financial struggles.
“Mine was a pair of bright emerald green Ralph chinos. I feel you,” one commenter wrote on AP News Entertainment’s TikTok.
However, not all reactions were purely celebratory.
When Y! Entertainment posted the story, some readers questioned Winfrey’s storytelling style, with one person commenting, “Unlike many, I liked Oprah’s show- but I did not realize until this clip, that she’s fluent in Word Salad. The Ralph Lauren towels had ‘form?'”
The revelation also sparked conversations about Winfrey’s past criticism of other celebrities’ spending habits, particularly her 1998 interview with Toni Braxton.
During that controversial segment, Winfrey questioned Braxton about purchasing Gucci flatware during her financial difficulties, leading to a tense exchange that Braxton later described as deeply hurtful.
Toni Braxton’s financial problems weren’t caused by Gucci flatware.
— Yvette Carnell 🇺🇸 (@BreakingBrown) February 11, 2024
But Oprah turned everyone’s attention away from record labels & whether artists are fairly compensated.
Toni couldn’t manage money. That became the storyline, & the framing was intentional. pic.twitter.com/q8pWu9YDxE
The contrast wasn’t lost on social media users, with one Instagram commenter noting, “No wonder she was beating up on Toni!”
“Another dig at Toni … we know subs when we hear them,” wrote one social media user, referencing how the story seemed to contradict Winfrey’s earlier stance on responsible spending.
One person replied, “Do you know the difference between the price of RL towels and Gucci Flatware … cut it out.”
Winfrey’s relationship with Ralph Lauren has remained strong throughout her career, evolving from that first towel purchase into a genuine friendship spanning decades. She has consistently worn his designs to major events and played a significant role in celebrating his 50th anniversary in 2018.
In a tribute essay to Vogue, she wrote about how his brand “epitomizes who we are on our best days, comfortable in our wardrobe and confident in our skin.”
The Barbara Walters connection also proved influential beyond that initial interview, shaping Winfrey’s life decisions in unexpected ways. Walters’ struggles balancing career and motherhood actually influenced Winfrey’s choice to remain childless, demonstrating how that early professional relationship had a lasting personal impact.
Looking back at both the Ralph Lauren towels story and the social media reactions, it’s clear that Winfrey’s journey from struggling broadcaster to media empire builder continues to fascinate audiences.
