The talk show host, who wore L'Wren Scott for her finale appearances this week, was not always so sartorially savvy. Here we chart her fashion hits and misses...
She started her career in the Eighties, with big hair and even bigger shoulderpads. So for Oprah Winfrey, the fashion could only get better.
And while she's graduated from boxy trouser suits to elegant dresses by Carolina Herrera and Michael Kors, daily shows for 25 years mean that the outgoing talk show host's opportunities for faux pas have been countless.
Low points include a Nineties penchant for shiny fabrics, and some very dubious choices on her Australia visit - but she has managed to redeem herself thanks to clever stylists that understand her body shape and know what works on screen.
Bowing out in style: Oprah Winfrey wore two dresses by Mick Jagger's designer fiancée, L'Wren Scott, for her finale shows - an embellished lavender gown on Monday and Tuesday, and a fitted pink number today
Of course, like many women, Oprah's yo-yo weight has contributed, but some of her finest fashion moments were not when she was at her slimmest, but when she was at her healthiest - indicating that confidence is key to pulling off a challenging look.
Indeed the L'Wren Scott couture dress she wore for her finale show today was a triumph - the lavender hue flattered her skin tone, while the hand-embroidered rosettes added just the right amount of drama for the occasion.
In an interview for her magazine, O, Oprah's stylists described the challenge they faced each day.
Adam Glassman, who styles her for O, said: 'It's not easy to get someone dressed for five television shows a week - and make sure she's camera-ready from every angle, to boot.'
Kelly Hurliman, who chose outfits for the Oprah show, added: 'It's never been a relationship where I say, "You're wearing this today".
'Oprah knows what she likes, she knows her body. At the end of the day, what she's wearing always comes down to what she wants to wear. You wouldn't believe how often she's walked onstage having tried on something for the first time five minutes before.'
This is clear in her wardrobe choices. Certain colours and design features appear year after year - like the colour red, for example - a consistent winner for the star - and nipped-in waists, be it with a belt or figure-flattering ruching.
Classic tailoring suits her better than voluminous shapes, and simple styles that let her personality shine through have proved better choices than fussy designs that end up wearing her than the other way around.
Here we chart Oprah's fashion hits and misses over the years....
OPRAH'S FASHION FAILURES
Fussy: Oprah in a garish kaftan on a visit to Australia in December last year (left), and in an unfortunate dress by Richard Metzger at a party for the first anniversary of O Magazine in 2001 (right)
Shine on: The star appears to have had an unfortunate penchant for reflective fabrics. In Cape Town in 2003 (left), in New York in November 2006 (centre) and receiving a Daytime Emmy in 1992 (right)
OPRAH'S FASHION HITS
All-out glamour: Oprah won high praise at the Met Costume Institute gala in Oscar de la Renta last year (left), and in Zac Posen (right) at the Oscars in February
Red alert: Oprah at the California Governor's Conference in December 2004 (left), at the Legends Ball in May 2005 (centre) and at the opening of the Hearst Tower in October 2006 (right)
Keeping it simple: Monochrome hues and elegant tailoring work have served Oprah well. At the theatre in New York in 2006 (left), at a premiere in 2005 (centre) and at a benefit in New York in 2004 (right)
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