Kris Jenner, 70, and Oprah Winfrey, 72, have kicked off a lavish girls' trip in Mallorca, Spain, embarking on a boating vacation together. This marks their second consecutive summer vacation in the region, following a trip last year aboard David Geffen's luxury superyacht.
Jenner, the matriarch of the Kardashian-Jenner family, was seen arriving in a polka dot dress, a wide-brimmed black hat, sunglasses, and ballet flats. She accessorized her look with large diamond earrings and carried a matching Hermès tote bag. Winfrey, the former talk show host, opted for a cropped white button-up shirt paired with high-waisted khaki trousers and white sneakers.
Last summer, Jenner and Winfrey were joined on their Spanish vacation by Winfrey's longtime friend, Gayle King, 71. During that trip, Jenner gifted Winfrey and King pieces from her daughter Kim Kardashian's SKIMS x Roberto Cavalli collection. Photos shared on social media showed the trio modeling the boldly printed kaftans while on a boat.
Jenner and Winfrey have maintained a friendship for years, which appeared to deepen when they attended Jeff Bezos and Lauren Sanchez's Italian wedding last summer. In 2012, Winfrey interviewed the Kardashian family at their home, an event Jenner later described on Twitter (now X) as the "Best day ever."
Jenner has spoken publicly about undergoing a facelift approximately 15 years after her first cosmetic surgery, describing it as her way of "aging gracefully" and being the "best version of myself." Winfrey, meanwhile, has openly discussed her significant weight loss achieved with the use of a GLP-1 medication.