Oprah Winfrey & Gayle King Proved They're The Ultimate BFFs With These Matching Outfits

If you've never worn matching outfits with your bestie, are you even really friends? Oprah Winfrey and Gayle King have been friends for 50 years, proving they're the ultimate BFFs with their frequent coordinating outfits. The journalists met while working at a Baltimore news station in 1976 and have been inseparable since. From road trips and award shows attended together to joined TV interviews and years of birthday presents flowing between them, it's no surprise that King and Winfrey began to mirror each other's style. 

In fact, as sisters do, King has been known to raid her bestie's closet from time to time, an insight revealed on "The Oprah Winfrey Show" in 1997. During the episode, Winfrey, with the audience's input, helped King pick a gown for the Primetime Emmy Awards, an event they would both attend, per Oprah.com. All friendships are different, and while a subtle moment proved HGTV's Christina Haack & Heather Rae El Moussa's friendship is 100% real, fashion serves as a testament to King and Winfrey's bond.

Ultimate BFFs Gayle King and Oprah Winfrey attended the grand opening for the Obama Presidential Center in June 2026, and they were twinning. Each journalist wore pastel blazer ensembles with loose bottoms. King wore a light-blue belted wide-legged jumpsuit with a matching snake-effect textured clutch, while Winfrey wore a belted A-line dress. King shared photos from the event, revealing that her daughter-in-law, who wore a three-piece blazer 'fit, attended the celebration as well.

In March 2026, Oprah Winfrey and Gayle King attended the Chloé Womenswear Fall/Winter 2026-2027 show in true "besties at Paris Fashion Week" style. The duo were pictured each wearing brown eyewear, light-colored tops, collared jackets, and wide-leg pants. Winfrey and King also carried similarly colored bags with one being simply beige and the other featuring a snakeskin pattern. Tying it all together, both wore pointed Chloé's Cleia snake-effect patterned pumps in different shades. The curved stiletto heels feature a gold-tone logo-engraved tip, making it the perfect addition to both of their looks.

In June 2025, Gayle King and Oprah Winfrey, who's had a head-turning transformation since using Ozempic, wore dresses of the same style for the 78th Annual Tony Awards. King wore a green vintage gown by Vicky Tiel Couture, while Winfrey wore a custom bejeweled Prada gown. Both dresses featured an off-the-shoulder bodice, a cinched waist-line, and a floor-length hem. Winfrey shared the sketch of her dress, captioning the Instagram post, "Thank you to @thetonyawards for having me and @prada for creating this work of art for me to wear." The duo also wore dangling earrings and wide shiny bracelets to complement their twinning looks.

In honor of Oprah Winfrey's 71st birthday, her bestie Gayle King shared several photos of the two during a trip to Italy on Instagram. In one of the pictures, the two posed in front of St. Mark's Basilica in Venice wearing blue-and-white striped dresses. King wore a form-fitting maxi dress, while her bestie opted for a knee-length button-down dress. In addition to similarly patterned outfits that prove older women can have fashion fun, they both posed with one hand extended to highlight the historic landmark behind them. 

In November 2024, Oprah Winfrey and Gayle King joined forces to promote the fashion brand Telfar on Oprah Daily's Instagram. Winfrey wore a beige floor-length hooded puffer jacket and a matching Shopper bag with King beside her wearing the same ensemble in yellow. A caption for the video read, "We like @telfarglobal—a Queens-born designer whose handbag is also on #OprahsFavoriteThings—and this hip and oversize unisex quilted nylon puffer with a hood will keep your body warm through the cold days!" Oprah Daily's creative director Adam Glassman also appeared in the video wearing the coat in dark brown.

Oprah Winfrey and Gayle King graced the cover of O, the Oprah Magazine for the September 2019 friendship issue with matching gold-toned clothing and complementary caramel-colored hair. Winfrey and King also wore the same shade of lipstick for the photo."The reason our friendship has worked for over 40 years, without arguments or fallouts, is that we've always been happy with our own lives," Winfrey captioned an Instagram post of the cover. "Ever since we met in 1976, we've been doing the same thing. Listening. Talking. Laughing (a lot). Building dreams. Cheering. Being a shoulder to cry on. Speaking the truth. Being the truth." Truly, they are BFF goals!