Siena Filippi, a New York-based vintage seller and content creator, didn’t have high expectations when she first tried the tool to get dressed. “I was mostly trying to have fun with it, but I also wanted to test its ability to take what I give it and actually create something cohesive,” Filippi says. In her TikTok video, she asked ChatGPT to tell her how to dress like “a trendy Pinterest girl living in New York City,” noting that she wanted her outfit to be cool enough to be “Instagrammable.” The AI suggested wearing a pair of high-waisted mom jeans and a graphic T-shirt with a slogan or design on it, styled with a black oversized blazer, chunky combat boots or platform sneakers, gold hoops in geometric shapes, and a black leather backpack. “I was impressed that it could do what it could do, but it wasn’t necessarily something that I was like, ‘Oh, I would totally wear this,’” she says.