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.”

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.

One more hope to emerge from Winfrey’s long-running series was the red Celine suit she wore in 2004, the year she broadly gifted each and every crowd part a Pontiac G6.

The look never happened in light of the fact that Winfrey’s closest companion, Gayle Lord — who thought of the uber vehicle giveaway — exhorted her not to wear it. In any case, Winfrey paid attention to her instinct and accepts that coordinating with the bows on the vehicles was the “best choice” right up to the present day. “It has brought us through years and years now.”

It even ruled when the show finished in 2011.

Winfrey finished off the period with a bang a shimmering aubergine outfit and a voluminous updo (This was the point at which I was going through my braid stage,” she made sense of). The dress was one of the main components prepared of time — the rest, from Beyoncé’s exhibition to Tom Hank’s appearance — was a shock.

With the 2024 Got Function meeting up, Individuals needed to incorporate Winfrey’s “fabulous” debut at style’s greatest night in 2010.

She went to close by Oscar de la Renta, who planned her sequin unsettled naval force outfit. She cherished de la Renta, who kicked the bucket in 2014, so much, she would’ve placed him responsible for her marriage outfit. “Had I at any point gotten hitched, really proceeded with the wedding, I generally needed an Oscar de la Renta outfit,” she said. “It was only a delight to have the option to be in his presence and to have him plan this dress only for me.”

A wedding she went to was that of Sovereign Harry and Meghan Markle’s in 2018, to which she wore an enlivened wide-overflow fascinator. “I grew up with cap wearing, church-going ladies and my mom was a major cap wearer thus I’ve generally cherished a wonderfully planned cap.”

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.”