It’s been five years since couturier to the stars, Oscar de la Renta, passed on. The protege of Cristobal Balenciaga had a career spanning almost five decades, bringing him through many eras of fashion. Whether it was during the grunge period of the 80s or the bohemian vibe brought forth in the decade after, De la Renta always made sure the women he dressed looked and felt beautiful.

But one constant throughout De la Renta’s designs were his glamorous gowns. First Ladies, Oscar-winning actresses, and Met Ball attendees have all flocked to his atelier for meticulous fittings in hopes that a photo of them would make a listicle just like this very one. We jest, but the point still stands: the ‘Couture Conquistador’ was a go-to name for any society lady wanting to look impeccably elegant. Casual was not at all his style.

De la Renta’s personable and charismatic nature was also probably what drove A-listers time and time again to his showroom. “He is the man every woman wants to hug!” Amal Clooney once said to Vogue about the designer who created her wedding dress. At the same time, he is also intensely competitive, once taking out a full-page ad on Women’s Wear Daily calling fashion critic Cathy Horyn a “stale 3-day old hamburger” after she called his show a “hot dog.” Winning at dominoes was a must for him as his New York Times obituary noted.

“We live in an era of globalization and the era of the woman. Never in the history of the world have women been more in control of their destiny.”

Oscar de la Renta

It’s the little things that make De la Renta more than just a man with a creative vision. Despite being 82, he still agreed to be part of Anna Wintour’s “73 Questions” video series, a testament to his determination to stay relevant by embracing social media. His eponymous fashion label grew 50 percent despite him being stricken with cancer in the last eight years of his career. De la Renta had a drive, and nothing was going to slow him down.

In memory of his legacy, we’re taking a throwback journey into his fashion archives and seeking out some of his best gown designs ever.