Oprah Chicly Upgrades Double Denim With Chloé’s Revived It Bag

There’s your average Canadian tuxedo—and then, there’s Oprah Winfrey’s. For her final appearance on The Late Show With Stephen Colbert, the renowned actress, producer, and television host stepped out in a stylish take on double denim with a surprise It girl twist.

While arriving to Colbert’s studio in New York City, Oprah wore a blue denim Chloé jacket. The piece featured lightly rounded sleeves, as well as two front pockets accented by gold-toned charms. Oprah chose to wear the casual outerwear with matching flared Chloé jeans, creating a bohemian take on the classic double-denim look. Her ensemble was complete with smooth, dark leather pumps and dangling gold earrings with pearl accents.

However, Oprah’s greatest Canadian tuxedo upgrade came from her handbag of choice: a Chloé Paddington satchel. The star’s warm brown leather version of the top-handled style featured its signature rivet accents, flap silhouette, and thick metal lock hardware. The piece instantly gave her ensemble a bohemian flair, in tandem with the French brand’s free-spirited, feminine aesthetic. It also marked the latest celebrity moment for the Paddington, which first reach it bag status in 2005 when it was introduced under then–creative director Phoebe Philo. The handbag has now returned to prominence after being reissued by creative director Chemena Kamali, with various colors and sizes seen on stars like Olivia Rodrigo, Addison Rae, Kendall Jenner, Katie Holmes, Olivia Wilde, and Daisy Edgar-Jones.

The moment continued Winfrey’s recent fashion hot streak, which has seen the multi-hyphenate truly enter her “fashion girl” era. After virally posing for Lapointe’s spring 2025 campaign, she made the rounds at Chanel, Stella McCartney, Zimmermann, and Chloé’s fall 2026 shows at Paris Fashion Week this winter—notably her first PFW outing in 20 years. In fact, Oprah also carried a cream leather Paddington bag at the brand’s craft-inspired runway show, making her latest appearance a reunion with the beloved accessory.

Though Oprah’s hardly the last celebrity to step out in double denim, her pairing of the matching set and Chloé’s It bag prove that staple and statement styles can always be made new again. After all, some pieces will always stand the test of time.