Tall Tales and Legends

Oscar's fashion empire—which also includes fragrances, handbags, shoes and home décor—is a family affair. His daughter, Eliza, is the vice president of licensing, as well as her father's "muse." Oscar says Eliza was the one who inspired him to create designs that appeal to a younger clientele.

"Today I'm dressing the mothers, the grandmothers, the daughters and the granddaughters," Oscar says. "That is what makes my business so successful."

Moises, Oscar's adopted son, is taking trendy to the next level. He's integrating hip t-shirts and jeans into the de la Renta line.

"For me, it's so wonderful [that] my family is working with me," Oscar says.