Michelle Obama recently stopped by Jimmy Kimmel Live! and delighted viewers with a personal story about an unforgettable moment early in her friendship with Oprah Winfrey. While chatting with Kimmel, the former first lady recalled what she called an “extravagant Oprah gesture” that followed their very first meeting.
Michelle Obama shares ‘Oprah gesture’ story from first meet on ‘Jimmy Kimmel Live!’
Obama explained that she met Winfrey in 2005 for an interview with O, The Oprah Magazine. After the sit-down, Winfrey surprised her with an exceptionally thoughtful thank-you gift: two tailored Ralph Lauren suits and a selection of the designer’s signature cable-knit sweaters. Obama described the gesture as generous and unexpected, noting that it marked her first real introduction to luxury fashion.
In her new book, The Look, which hits shelves on November 4, Obama expands on the moment and what it meant to her at the time. She writes that running her hands over the fabric helped her understand the appeal of designer clothing. When she tried the suits, she immediately noticed the precision of the tailoring and the quality of the construction. The perfectly cut pieces, she recalled, hugged her frame in all the right places.
Oprah and the Obamas grew close in the years leading up to Barack Obama’s 2008 presidential election. Winfrey publicly endorsed him and later explained that her personal connection to the couple played a role in her support.
Michelle Obama would later become widely celebrated for her fashion choices during her time as first lady from 2009 to 2017. In The Look, she reflects on how style became a form of self-expression and confidence during her years in the public eye.
Michelle recently said on the show that she and her husband, former President Barack Obama, had plans to meet the Reiners on the night they died. “We’ve known them for many, many years, and we were supposed to be seeing them that night,” she said.
