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.

1
Hillary Clinton, 1997

While De la Renta has dressed four First Ladies, none of his White House-living clients have been as iconic as Hillary Clinton. “He’s been working for 20 years to turn me into a fashion icon,” Clinton was quoted as saying by the New York Times. For her husband’s second presidential inauguration ball in 1997, she wore the gown (pictured above) that became one of her most memorable looks.

2
Amal Clooney, 2014

There’s something timeless and graceful about Amal Clooney’s style, and anything Oscar de la Renta is the perfect fit for the lawyer’s wardrobe. However, the pinnacle of their collaboration might very well be Clooney’s dress for her wedding to actor George Clooney: an ivory tulle gown in mille-feuille adorned with enough Chantilly lace and embroidery for a generation of wedding gowns.

3
Sarah Jessica Parker, 2014

It’s no secret that Sarah Jessica Parker is a lover of all-things-fashion, and her friendship with De la Renta was one that cannot be counted out of the equation. The designer is responsible for a number of her looks, including a Met Ball gown that was inspired by Charles James (pictured here). “I was sitting with Anna one day and she said, ‘Ask Oscar, of course ask him!’” Parker said of her decision to get De la Renta to create her gown. “So I rang him that day and said, ‘Would you consider building something for me for the Met Ball?’”

4
Carrie Bradshaw, 2004

Carrie Bradshaw and Aleksandr Petrovsky might not have been a match, but for one brief moment in Sex and the City, it was a fashion moment for the ages thanks to the off-screen assistance of De la Renta. Bradshaw had her eyes set on a hot pink OdlR dress that Petrovsky, being friends with the designer, gifts to her as a surprise. This crossover between fashion and popular culture was the true match made in a sartorial heaven.

5
Audrey Hepburn, 1988

The queen of the Hollywood Glamour Girls Audrey Hepburn often turned to De la Renta to dress the starlet, be it on or off screen. His most outlandish creation for the elfin beauty would be a red feathered dress that, while a departure from De la Renta’s usual ethos of simplistic beauty, was in hindsight proof of his revolutionary, trendsetting designs.

Josiah Neo
Writer
Josiah Neo is a tech writer who contributes occasionally to the fashion, travel, and culture beats. When he’s not busy keeping up with the keynotes, he’s probably stuffing his face with the best Melbournian donuts (at Shortstop, BTW) or watching his favourite esports team, the Los Angeles Valiant, pummel their opponents into oblivion.