Oprah Winfrey Looks Back on Her Iconic Style Moments, from Her Beloved PJs to Royal Wedding Hat (Exclusive)

In celebration of PEOPLE's 50th anniversary, the talk show host breaks down her most memorable outfits

Oprah Winfrey has a lot of memorable fashion moments and some incredible stories to go with them.

In celebration of PEOPLE’s 50th anniversary, the talk show host and producer, 70, reflects on her most iconic looks from the past five decades (did you know that she loves a designer moment as much as she does her pajamas?).

Walking down memory lane, Winfrey recalls some of the style hacks she perfected early on in her career. During her time as a news anchor on WJZ-TV, she used to blow dry her hair by rolling down the windows of her Chevrolet Chevette.

But when The Oprah Winfrey Show officially kicked off in 1986, she had a glam team, including a local designer, hairstylist Andre Walker and makeup artist Roosevelt Cartwright. She still had to style herself when she made her debut in a statement blazer and earrings “as big as envelopes.”

Related: PEOPLE's 50th Anniversary: The Celebration Continues

<p>SplashNews.com</p> Oprah Winfrey debuts "The Oprah Winfrey Show" in 1986


Oprah Winfrey debuts "The Oprah Winfrey Show" in 1986

Ten years later, in 1996, Winfrey introduced her “Oprah’s Favorite Things” segment in her favorite look of all time — flannel pajamas. “My favorite thing to wear still to this day is pajamas and my way of dressing is comfort first and I like anything that feels like pajamas and looks like pajamas,” Winfrey says.

Related: Oprah Winfrey Shares Her Remarkable Journey and What She’s Learned: 'I'm Grateful for It All'

<p>AP Photo/Harpo Productions</p> Oprah Winfrey in Celine on "The Oprah Winfrey Show" in 2004

AP Photo/Harpo Productions

Oprah Winfrey in Celine on "The Oprah Winfrey Show" in 2004

Another look to come out of Winfrey’s long-running series was the red Celine suit she wore in 2004, the year she famously gifted every single audience member a Pontiac G6.

The look almost never happened because Winfrey’s best friend, Gayle King — who came up with the mega car giveaway — advised her not to wear it. But Winfrey trusted her gut and believes that matching with the bows on the cars was the “best decision” to this day. “It has carried us through a couple of decades now.”

It even reigned supreme when the show ended in 2011.

Winfrey closed out the era with a bang a sparkly aubergine gown and a voluminous updo (This was when I was going through my ponytail phase,” she explained). The dress was one of the only elements planned ahead of time — the rest, from Beyoncé’s performance to Tom Hank’s appearance — was a surprise.

<p>BILLY FARRELL/Patrick McMullan via Getty Images</p> Oprah Winfrey attends the 2010 Met Gala

BILLY FARRELL/Patrick McMullan via Getty Images

Oprah Winfrey attends the 2010 Met Gala

With the 2024 Met Gala coming up, PEOPLE had to include Winfrey’s “fantastic” debut at fashion’s biggest night in 2010.

She attended alongside Oscar de la Renta, who designed her sequin ruffled navy gown. She loved de la Renta, who died in 2014, so much, she would’ve put him in charge of her bridal gown. “Had I ever gotten married, actually went through with the wedding, I always wanted an Oscar de la Renta gown,” she said. "It was just a joy to be able to be in his presence and to have him design this dress just for me."

A wedding she did attend was that of Prince Harry and Meghan Markle’s in 2018, to which she wore a decorated wide-brim fascinator. “I grew up with hat-wearing, church-going women and my mother was a big hat wearer and so I’ve always loved a beautifully designed hat.”

Winfrey’s last fashion era was splashed in all shades of purple for, you guessed it, The Color Purple press tour.

“For a long time people thought it was my favorite color. It’s never been my favorite color,” she admits to PEOPLE. After ridding her closet of all and any vibrant clothing (“For 25 years I had to wear color and I just kind of got tired of it,” she says), Winfrey, the movie's co-producer, busted out her boldest pieces for the special occasion. "I’m doing for the purple what Barbie did for the pink, okay.”

For more on our 50th Anniversary, check out our special digital issue, and pick up a star-studded copy of PEOPLE, on newsstands April 12.

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