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Rachel Roy’s American Dream: From Working at the Mall to Dressing Michelle Obama

Rachel Roy is known for dressing the likes of Michelle Obama and Kim Kardashian, but the high-profile designer got her start in fashion like a lot of other teenagers—a job at the local mall.

Roy started working at the now-defunct brand Contempo Casuals when she was 14—the age her father, an immigrant from India, expected everyone to start contributing to the family’s expenses.

“He dropped me off at McDonald’s,” Roy said at the Fortune Most Powerful Women Next Gen conference in San Francisco on Wednesday. “I love McDonald’s, but I didn’t want to work there.”

Instead she took a bus to the mall and started working in retail, where she learned that “clothing could transform myself and other people.”

Her dad’s perspective also pushed her to start her own company. “He would say things like, you’re living in a country where you can start your own business,” she said.

Roy also talked about her legal battle with Jones Group. She had a joint venture with the company but kept creative control. When Jones tried to sell her trademark, Roy sued. She said that the first lawyer she hired pushed her to settle but she decided “I would rather lose it in a fair fight than just give up.”

She caught a break during a lunch with her friend Melania Trump, when a man came over to the table to say hello. It was Donald Trump’s lawyer. She went home, Googled him, and found out he was one of the most feared lawyers on Wall Street. “Perfect,” she said. “The cost of doing business is sometimes letting someone do the fighting for you.”

Roy ended up winning the legal battle, and her brands are now majority owned by privately held Topson Downs. Roy said she much prefers working for a private company where it’s much easier to make changes.

“There’s nothing like freedom,” she said.

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