Oprah Winfrey has been making stylish rounds as of late, stepping out everywhere from Paris Fashion Week to high-profile podcast appearances. Most recently, she was spotted in New York City heading into a taping of The Late Show with Stephen Colbert, delivering a masterclass in New York street style.
For the occasion, Oprah opted for a head-to-toe denim look from Chloé, proving once again that the classic fabric can feel both polished and contemporary. The look featured a structured denim top paired with perfectly tailored bootcut jeans—a Canadian tuxedo with a bit of a flair. The jeans subtly flared at the hem, creating a flattering, elongated line that worked seamlessly with her choice of footwear—sleek brown boots that grounded the look with a rich, earthy tone.
We’re equally obsessing over her must-have accessories. Oprah carried the highly coveted Paddington bag in a deep chocolate brown, a piece that has quickly reemerged as one of the season’s must-have items. The bag added both a trendy feel and a sense of nostalgia, nodding to early 2000s fashion while still feeling entirely current. She paired the look with oversized shield-frame sunglasses, bringing edge to the otherwise classic outfit.
From Paris to New York, Oprah continues to demonstrate that true style lies in the details. She reminds us how undeniably chic she is with an effortless blend of timeless staples and trend-forward pieces.