Claire Sinclair, born Clairissa Irene Riccio on May 25, 1991, in Los Angeles, California, was raised in a middle-class Italian-American family. Of Caucasian descent, she grew up with a single mother, Lisa Riccio, and has no publicly documented siblings. She attended Woodrow Wilson High School in Los Angeles, where she was a cheerleader and developed an interest in vintage fashion and pin-up culture. Details about her higher education are not available, as her modeling career began early and became her primary focus. Sinclair’s entry into modeling started at 14 when she created a MySpace profile showcasing her pin-up-inspired photos, which caught the attention of a Playboy scout. Encouraged by her mother, she submitted photos and was selected as Playmate of the Month for October 2010, with her pictorial shot by Stephen Wayda. In 2011, she was named Playmate of the Year, a milestone celebrated at the Playboy Mansion. Her Playboy work includes over a dozen photosets, such as “Vintage Vixen” (2010) and “Playmate of the Year 2011,” featured on Playboy Plus and platforms like BabesRater, where her galleries are highly rated (e.g., 9.4/10). She appeared in Playboy TV shows like The Girls Next Door (2010–2011), Playboy’s Beach House, and Playboy Radio, as well as videos including Playmate Profiles and behind-the-scenes shoots. Sinclair also worked as a Bunny at the Las Vegas Playboy Club and starred in Holly Madison’s Peepshow at Planet Hollywood, blending burlesque with her pin-up persona. Beyond Playboy, Sinclair has pursued acting and entrepreneurship. She had small roles in films like K-11 (2012) and appeared on TV shows such as Holly’s World (2010–2011).