Oscar de la Renta (who passed away Monday night at 82) had a huge Hollywood following — but no A-lister’s relationship was more longterm or loyal than Sarah Jessica Parker‘s. The two New Yorkers shared an innate sense of graciousness and elegance, a love of mixing romance and whimsy in their style and a knack for turning red carpets into a major event — not to mention the distinction of often being referred to by their initials. And Parker loved to wear his designs again and again, from vintage gowns to graphic ones, elegant day looks to eye-popping evening ensembles. Below, check out five noteworthy collaborations between the two that give a sense of their fashionable friendship.

Larry Busacca/Getty

That Met Gala Dress: No gown was more talked about than Parker’s at this year’s Metropolitan Museum of Art Costume Institute Gala, for which she was a co-chair. From the front, the ballgown paid tribute to the night’s honoree, Charles James, but from the back, it was all about de la Renta: She had him “sign his name” across the train, which was designed to look like a dress form. “I said to Mr. de la Renta, Please let me use scarlet embroidery thread and flash your name across the back,” Parker said at the time. “It was my idea. He would never in a million years have done it, he’s far too modest.”

Jemal Countess/Getty

From “Ladies Who Lunch” to Leather & Ladylike: Many stars who donned de la Renta did so in pearls and updos, afraid to deviate from the designer’s simple, elegant approach. Parker had no such qualms: She’d take one of his most feminine gowns (like this pink one worn to an N.Y.C. amfAR gala in 2012) and give it her own twist, adding a Theyskens’ Theory leather jacket and white motorcycle gloves. Such an irreverent spin on de la Renta’s designs might have you clutching pearls of your own, but their friendship meant that she could take big risks — and pull them off — in his gowns.

RELATED PHOTOS: 28 Showstopping Red Carpet Gowns Designed by Oscar de la Renta

Jamie McCarthy/Getty

Giving Him His Due: When de la Renta was honored with the Lifetime Achievement Award by the Couture Council in 2012, Parker was at his table wearing a sweetly sassy red checked dress by the designer. In addition to paying tribute to him with her choice of clothing, she joined the crowd in a standing ovation — and was rewarded with a fatherly peck on the forehead from the legendary designer.

Jason Kirk/Liaison/Getty

That Emmys Dress: The ballerina-inspired dress Parker wore to the 2000 Emmys landed her on countless worst-dressed lists, both then and ever since. But (with the exception of that silly floral arm band), we think this look gets a bad rap. It’s a little on-the-nose, sure, but it’s also flattering and undeniably fun, and Parker looked like she had a ball wearing it. We can’t imagine a more perfect embodiment of the two stars’ combined design sensibilities — and we always support a star who takes a risk with love.

Everett

The “Date With the Russian” Dress: When Parker’s onscreen alter ego, Carrie Bradshaw, was getting a little bummed out by her serious romance with artist Alexander Petrovsky, Parker knew exactly the perfect present for him to give Carrie to cheer her up: a pink Oscar de la Renta cocktail dress. And it looked equally alluring at the Metropolitan Opera opening night as it did when Petrovsky squired her to McDonald’s later that evening. It’s one of the most memorable costuming choices on Sex and the City, and that’s saying something considering the show was all about memorable costuming choices.

Which Parker/de la Renta moment was your favorite? Any we missed?

–Alex Apatoff