news | March 30, 2026

Surprising Things About The Gap You Didn't Know

Over the years, the Gap has been featured everywhere from late-night TV to a historical trial. In 1994, SNL poked fun at the clothing chain with sketches featuring David Spade, Adam Sandler, and Chris ("Lay off me, I'm STARVING!") Farley as the "Gap Girls," a trio of snarky retail workers. 

Back in 1996, Sharon Stone got plenty of notice at the Academy Awards when she arrived in an Armani tuxedo jacket with a Gap turtleneck underneath. The actress later explained to Us Weekly that she was supposed to be wearing a Vera Wang gown, but the driver who delivered the dress accidentally ran over the box with his truck, ruining it. With less than 24 hours to go before the ceremony, Stone called a costume designer, who went through her closet and pulled together the alternate outfit. Two years later, she raised eyebrows at the Oscars again by pairing a Wang skirt with a white Gap button-down — this time her own choice (via The Zoe Report).

But the most famous piece of Gapwear was the one that almost brought down a president. During the 1998 impeachment trial of Bill Clinton, it was revealed that the president had carried on a sexual relationship with intern Monica Lewinsky. During one of their encounters, she wore a blue Gap shirtdress that got stained with Clinton's... um... DNA. Lewinsky was urged to keep it as evidence, and continued to hang on to it the "same way people keep sweaty T-shirts from a rock star," she explained in an interview years later (via the New York Post).