In 1994, recognizing the then-limited clothing options available to fashion-forward women, Chaiken teamed with a friend, Pamela Capone, to found Chaiken and Capone. "I wanted to create something that spoke to who I am, and I came up with the idea of a clothing company to create clothes for women like myself," Chaiken said in an interview in 2004. Chaiken and Capone's first offering included a successful line of pants, which were described as "revolutionizing the pants market." Initially, Capone focused on design while Chaiken focused on the business and business strategy. In 1998, she bought out Capone; by 1999, the line was being carried in more than 400 boutiques and high-end retailers, including Barneys New York, Saks Fifth Avenue, and Nordstrom. Chaiken, while primarily focused on growing the company, subsequently expanded her role as CEO to include clothing and accessory design. In 2001, at the request of Chaiken clients including Cindy Crawford and Vendela, Chaiken created a maternity line, Chaiken With Child. Chaiken and Capone's signature pants, with elastic in the waistband, and an "emphatic lack of ugly front pouches," were successful and orders at high-end department mandated wide production. "Business school 101 is find a need and fill it," Chaiken said. The Chaiken with Child spring collection in 2012 represented 15% of Chaiken and Capone's overall sales. in 2008, Chaiken—a single mother of two—went on a two-year hiatus. Returning to the company in 2010, she reconfigured her late-1990s dress line Anonymity to include all categories and relaunched it through QVC. A ready-to-wear collection returned to the market in 2010 and, although successfully relaunched as Chaiken and Capone, the company became known as simply Chaiken in 2012. In 2014, she was honored as a "Woman to Watch" by Jewish Women International. In 2015, she retired from Fashion and is currently focusing on her family and her philanthropic work.