More column inches and tabloid headlines have been devoted to Oprah Winfrey’s yo-yoing weight and fluctuating waistline over the years than to her style choices. The subject drew the strongest ratings for the former talk-show queen’s eponymous vehicle, The Oprah Winfrey Show – the highest-rated talk show in television history – when, in a notable episode in 1988, she strutted on stage in figure-hugging denim, towing a trolley laden with 67lbs (30kg) of animal fat, representing how much weight she had recently shed. Winfrey confessed that, two decades on, she still had to work with editors from O, The Oprah Magazine to “camouflage” her figure. “Here I am, one of the most visible people in the world, trying not to be seen on the cover of my own magazine,” she admitted, with her trademark intimacy.

Size aside, Winfrey’s image – bar the odd off-duty tracksuit and some better-forgotten lapses in the ’80s (and who was immune?) – has become ever more polished over the years, like any celebrity with access to professional stylists. Her current glossy locks and designer gear are worlds away from the cute get-ups she first wore as a young anchor in Baltimore, such as a patterned blouse and tank top with an afro (Winfrey said she settled on said ’do after a bad perm made her hair fall out). From the sexy, fitted fire-engine-red Céline power suit worn on the 19th season of The Oprah Winfrey Show to the feminine baby-pink TSE Sweater and Louis Vuitton skirt she donned for her much-spoofed ‘couch-jumping’ Tom Cruise interview back in May 2005, Winfrey is a woman who enjoys fashion, focusing on pieces that fit well. She prefers draped jersey fabrics and v-shaped necklines to accentuate her curves and décolletage – to make her feel good over following trends. Winfrey favours soft, figure-hugging designs and bold colours, such as the hot-pink wrap dress she wore to the Los Angeles premiere of Lee Daniels’ The Butler, in which she stars.

Yet, working with stylist Kelly Hurliman, Oprah is also up for testing new styles, be it the uncharacteristically sober grey Carolina Herrera dress she wore to announce the end of The Oprah Winfrey Show (she wound it down in 2008 to launch her cable channel, OWN: The Oprah Winfrey Network) or the Valentino gown she wore for an interview with US Vogue’s André Leon Talley in 2009. It got the thumbs-up from the discerning Talley, but Winfrey grumbled that she felt like she was wearing a choir robe. She has also exhibited a varied roster of hairstyles throughout her career, from a short, straight ’do with a fringe in the late ’90s to a luxurious, Pocahontas-style weave to the joyously over-the-top afro worn on the cover of the September 2013 issue of O.

Billion-dollar baby

As the epitome of the rags-to-riches American Dream, self-made Winfrey – born into poverty in rural Mississippi to a teenage single mother, today tops Forbes’ annual Celebrity 100 ranking of the most powerful celebrities in the world with an estimated net worth of $2.9bn. With a magazine, TV network and production company under her (brand) name, she has inevitably developed expensive taste.

Despite her formidable spending power, however, luxury retailers don’t always open their cash registers to her custom. On several occasions, Winfrey – the first black female billionaire – has reportedly been turned away from luxury outlets. For women of colour, being a haute-couture customer is still fraught with complications, it seems.

Two key incidents stand out. In 2005, the broadcaster complained that she had been turned away from the flagship Hermès store in Paris at closing time – even though there were other people shopping in the store; in response, Robert Chavez, the CEO of Hermès USA, made a public apology on The Oprah Winfrey Show.

More recently, Winfrey claimed a sales assistant in a store in Zurich refused to let her see a $38,000 bag that was kept behind a screen, saying that it was “too expensive” for her. “I wanted to create a Pretty Woman moment and come back and buy everything and say, ‘Big mistake’, but then I thought she’d get a commission, so let’s not do that,” Winfrey told Larry King in August. Swiss tourism officials soon issued an apology, although the shop challenged Winfrey’s accusation.

Game for a laugh

Not one to worry over her wardrobe, Oprah likes to follow her instincts, for better or for worse. Take the time she donned a plaid Alexander McQueen skirt on one of her shows. “I wasn’t even going to show it to her because I knew plaid wool probably wouldn’t look great on TV, but she saw it and loved it and said, ‘Let’s wear it on today’s show’. And it wound up looking like a fringed sofa blanket...” lamented Kelly Hurliman, in conversation with Adam Glassman, Creative Director of O Magazine, for a feature on

Other admitted clangers included the buttercup maxi dress Winfrey slipped into between tapings and decided to keep on. “She felt cute in her schmatte [rags] and wanted to know why she couldn’t do the next show that way. ‘I’m comfortable, I feel like me!’” Hurliman recalls Winfrey saying, with Glassman gleefully interjecting, “Sure, go do it – go look like a shlumpadinka [Oprah’s term for slumpy housewives].”

One saggy, rust-hued knit dress left Hurliman itching to interrupt filming and drag Winfrey back to the dressing room. “You really have to try things on and take a hard look, head to toe – and, of course, we didn’t have time. When I glanced at the monitor, I said, for the first time ever, ‘Oh my God. Should we stop and have her change?’ But before I finished that sentence, she’d started the show,” says Hurliman. “I know that everyone has good and bad days, but unfortunately, our bad days were lived out in front of millions of people...” With five shows to dress Winfrey for each week, without fitting-time, Hurliman’s was always a precarious job. “I usually get the last three minutes to dress her before you see her walk out onstage,” Hurliman admits, in another Q&A on “I’ve come to learn that, to Oprah, it’s just like walking out to any normal job – no trying on clothes for hours and no fuss...there’s just more important things to get done in a day.”

The fact Hurliman and Glassman get to publically dissect Winfrey’s wardrobe on her very own website is unheard of in the celebrity world, suggesting Winfrey is not the ‘sack the stylist’ type and, more importantly, has a healthy sense of humour. “She laughed about it; she’ll never let any of us live it down, but she can laugh,” Glassman deadpans in reference to a long, pale skirt and dark-pink billowing blouse combo Winfrey wore for an Australian episode of her show which prompted her to comment: “I now have no ego because I was on stage wearing a balloon next to Nicole Kidman”.

Such style missteps, as with all the personal struggles she’s shared with her audience, only serve to further humanise Winfrey to her devoted  audience. Her choice to sometimes pooh-pooh her stylist’s advice also points to an authentic woman who knows her mind and is willing to take risks. Well-documented demons aside, she’s comfortable enough with herself to accept her own choices. “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,” says Hurliman. The stylist’s favourite-ever Winfrey outfit? The metallic wine-coloured 2007 post-Oscar show dress specially designed by Rachel Roy, a belted-trenchcoat design that “looked great onstage”.

Just like the tongue-in-cheek January cover of O magazine marking Winfrey’s 60th birthday, which sees the broadcaster in a pair of yellow PJs with her hair in rollers sizing up a ‘glamazon’ version of herself in a gold gown, Winfrey is just as comfortable showing her true, warts-and-all self as she is playing princess. The message? This media mogul is no diva, but she has earned her place to shine and is going to darn well enjoy it. With or without expensive accessories.

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