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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.^[2] She graduated from Barrington High School in Barrington, Illinois (1976)[1] and the School of the Art Institute of Chicago (1981).^[3]

Known for what The New York Times has called "flirty, vibrantly colored dresses and tops in wispy materials"^[4] that have "a whiff of the carefree, simple spirit" of Claire McCardell,^[5] Rowley launched her business in 1981^[6] or 1983^[7] with $3,000 in seed money from one of her grandmothers.^[8] "Several months later, she held a fashion show in her apartment, inviting every important fashion editor in New York, as well as Andy Warhol and a smattering of movie stars -- none of whom she knew."^[9]

Since then the Cynthia Rowley Collection, incorporated in 1988,^[10] has grown to include women's wear, shoes, handbags, eyewear, belts, dishes, legwear, hats, color cosmetics, and fragrance. It is sold in Cynthia Rowley shops in New York, Chicago, East Hampton, Japan, Hong Kong and Taiwan, and in the Cynthia Rowley online boutique. Shops in Beijing and Shanghai are opening soon.^{[citation needed]} The collection is also represented in better department and specialty stores both domestically and internationally.

The Council of Fashion Designers of America honored Rowley with a Perry Ellis Award for New Fashion Talent (1994)^[11][12] and a nomination for the Perry Ellis Award for New Menswear Design Talent.

The designer and Ilene Rosenzweig, her best friend and a former reporter for The New York Times, also created a line of home accessories called Swell, which made its debut at Target in 2003.^[13]

^{Rowley has appeared as a judge on the reality television programs Project Runway and Design Star and has been a guest on The Today Show, Good Morning America, The Oprah Winfrey Show, and the Late Show with David Letterman, among other programs.}

^{She has written and co-written several books:}

• ^{Slim: A Fantasy Memoir (Random House, 2007)}
• ^{The Swell Dressed Party (with co-author Ilene Rosenzweig, Atria, 2005)}
• ^{Swell Holiday (with Rosenzweig, Atria, 2003)}
• ^{Home Swell Home (with Rosenzweig, Atria, 2002)}