Oprah's Natural Beauty: A Behind-the-Scenes Look
You know how some people are always perfectly put together in public? Oprah Winfrey is one of those people. But here's the thing—she’s not afraid to show her true, unglammed-up self on social media. In fact, back in 2014, the legendary talk show host gave us all a sneak peek into her pre-glam routine for the Screen Actors Guild Awards. She posted a candid photo on Instagram, proving that even icons have moments where they're just being themselves before the magic happens.
Behind the Scenes with Oprah's Glam Squad
Not long after sharing her no-makeup selfie, Oprah went a step further and gave fans a behind-the-scenes look at her glam squad in action. She posted another Instagram video, this time showcasing her team working their magic. For the big night, she rocked a stunning purple Badgley Mischka dress paired with a voluminous, curly hairstyle and dramatic smoky eye makeup. Safe to say, the result was nothing short of perfection!
View this post on InstagramGettin' ready for SAG awards calling in my Glam squad. # Need 'em!
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Contouring Secrets from Oprah's Makeup Artist
Oprah’s makeup artist, Derrick Rutledge, has been sharing some insider tips with fans. He recommends keeping things simple by using just three key products: a base foundation, a contour shade that’s only one or two shades darker than the base, and a highlighter. The trick? Highlight the areas you want to emphasize and use the contour shade to define the hollows of your cheeks, your jawline, and your temples. Finish off by blending everything with a damp sponge and setting it all with a light dusting of loose powder. Voilà! You’ve got a polished look that’s ready for the red carpet—or even just your living room mirror.
From Oprah to Michelle Obama: The Art of Contouring
Derrick didn’t stop at Oprah. He also worked with another iconic figure—Michelle Obama. In an interview with The Globe and Mail in 2014, Derrick revealed that while Oprah respected the First Lady’s precedence, he had the privilege of working with both women for a while. Given their hectic schedules, he even taught Michelle how to do her own makeup in case he wasn’t available. “They both have the busiest schedules I’ve ever seen,” Derrick said. “The transition between the two was amicable.” Talk about multitasking queens!
View this post on InstagramGlam squad in action ! #SAGawards
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Oprah’s Generosity and Makeup Mishaps
Derrick isn’t the only one who’s had glowing things to say about Oprah. According to him, she’s not only a great teacher but also an incredibly giving person. “Her generosity is what makes her so successful,” he explained. But even legends like Oprah aren’t immune to makeup blunders. During a segment on her long-running talk show called “Crimes Against Cosmetics,” makeup artist Reggie Wells playfully teased Oprah about her blending skills and puffy eyelids. It just goes to show that no matter how famous or talented you are, there’s always room for improvement. And honestly? That’s kind of beautiful.
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