The first time Sharon Stone wore The Gap to the Oscars, it was an accident. As a nominee in 1996 for Casino, she had two options percolating: One, a Vera Wang dress in a fabric that just wasn’t working out, and a second that literally fell off the FedEx truck the day before and was run over, leaving a tire track down the front of the frock. Let’s be real: No matter how well this worked out, I will always be sad that Sharon Stone didn’t wear a pink dress with a Michelin mark all over it. Or driven over it ten more times herself to try and make a pattern out of it. We missed Road Rage on the Red Carpet, and for that I grieve.

Instead, Basic Instinct costumer Ellen Mirojnick saved the day: Sharon invited her over in a panic and threw basically anything she had in her closet on the floor, and Mirojnick paired a Valentino Skirt with the infamous Gap turtleneck and then tossed over it an Armani tuxedo dress that Stone wore as a coat (she took it off to present, I believe). It’s pretty amazing how that and a simple flower came together into an outfit that looks deliberate — and of course, the world leapt on the unusual intersection of what we’d now refer to as “high and low,” or “high fashion and high street.”

Sharon did it again two years later, this time… presumably on purpose?

Paramount / 20th Century Fox Oscars Party

That is a Vera Wang skirt — perhaps a make-up moment after the 1996 dress didn’t pan out — and a Gap collared shirt that she said was from her then-husband Phil Bronstein’s closet. I couldn’t find any anecdote about the decision-making process here, so please, if anyone has heard Sharon talk about it or knows anything more, share it in the comments. The entire look is deeply cool, though, and who knows, maybe she was emboldened to do it because The Gap had served her so well two years earlier. And honestly, between the two looks, this is the one I think of when I hear “Sharon Stone” and “Gap.” It may not have been the first, but because it appears to have been the one that was a more deliberate choice, it makes a louder fashion statement.

[Photos: Shutterstock, Getty]