One thing was certain: The man knew how to make women beautiful. In a career that spanned 58 years, Oscar de la Renta, who died on Oct. 20 at age 82, dressed some of the most powerful women of the past century, including four First Ladies. But he made his most indelible mark on Hollywood, designing for everyone from Sarah Jessica Parker to Oprah Winfrey. Here, EW looks back at a few of his dazzling creations.

By Lindsey Bahr
Updated October 24, 2014 at 04:00 AM EDT

Amy Adams, Oscars 2013
For her fourth nomination, Adams gave the designer a vintage photo that served as inspiration for her ethereal gown.

Penélope Cruz, Met Gala 2011
Cruz walked the Met Gala carpet on the arm of de la Renta and in one of his signature romantic designs.

Oprah Winfrey, Met Gala 2010
De la Renta lovingly referred to Winfrey’s ruffled ensemble as ”a queen-of-the-night gown.”

Cameron Diaz, Oscars 2010
Diaz topped best-dressed lists when she stepped out in this glittering, intricately embroidered gold gown.

Sarah Jessica Parker, Met Gala 2014
Parker had a long relationship with the designer that crisscrossed from the red carpet to the screen, culminating in this autographed frock. ”It was my idea,” she said. ”He would never in a million years have done it, he’s far too modest.”