Rowley is a native of Barrington, Illinois, an affluent northwestern suburb of Chicago. She is one of three children born to Ed Rowley, a former science teacher, and his wife, Clementine, who was a painter. Rowley made her first dress at age seven, and came from an artistically inclined family – her grandparents included the designer of the Pabst Blue Ribbon logo and a painter. She graduated from Barrington High School and the School of the Art Institute of Chicago. Rowley was kicked out of her junior yearart show at SAIC because her use of wings in her design was seen as over the top. In an interview with the Chicago Tribune, Rowley said that Marshall Field's had bought her first collection while she was still a student at SAIC.
Fashion career
In 1981, Rowley won an SAIC fellowship award in her senior year and used the money to move from Chicago to New York City. She then launched her career with $3,000 in seed money from one of her grandmothers. Since Rowley launched her first capsule collection in 1988, has grown to include women's wear, handbags, glasses, color cosmetics, fragrance, wetsuits and swimwear, home furnishings, bedding products, and office accessories. The designer also created a line of home accessories called Swell, based on a book series she co-wrote with friend Ilene Rosenzweig, which made its debut at Target in 2003. In 2011 Rowley presented the Mr. Powers collection, a limited menswear range named after her husband Bill Powers. Rowley's fashions are presented bi-annually at New York Fashion Week. Signature Cynthia Rowley stores are in New York City, Chicago, Montauk, Palm Beach, Malibu, Pacific Palisades, and Newport Beach as well as at the company's web store. Rowley's designs were described by The New York Times as "flirty, vibrantly colored dresses and tops in wispy materials" that have "a whiff of the carefree, simple spirit" of Claire McCardell.
Rowley has appeared as a judge on the reality television programs 24 Hour Catwalk, America's Next Top Model, Project Runway and Design Star and has been a guest on The Today Show, Good Morning America, The Oprah Winfrey Show, Gossip Girl, Celebrity Jeopardy, and the Late Show with David Letterman, among other programs. The TV seriesReturn to Amish on the TLCnetwork follows ex-Amish Kate Stoltzfus as she interns at Rowley's design company. She has written and co-written several books:
Rowley's first husband was photographer Tom Sullivan, who died of brain cancer at the age of 32 in 1994. Rowley married William Keenan Jr., a Brooklyn sculptor, with whom she had a daughter, Kit Clementine Keenan. She is known Keenan released her own line of clothing in 2018, titled KIT. In 2019 Cynthia and her daughter Kit created a podcast together called Ageless. After Rowley and Keenan Jr. separated, she married William Powers, an art dealer, owner of the Half Gallery in Manhattan's Upper East Side, and writer, on September 17, 2005, at the home of photographer Peter Beard..