Kaia Gerber Slips Into a Leather-on-Leather Late Night Outfit in New York City

Kaia Gerber let her leather-on-leather outfit do the talking on a Sept. 30 meet-up with Cole Bennett. The outing comes amid rumors that she and actor Austin Butler—who have not been photographed together since August—have broken up after three years of dating.

That said, the 23-year-old model didn't appear fazed as she strolled into a show with 28-year-old Bennet on Monday evening. The Bottoms star wore black from head to toe, beginning with a leather motorcycle jacket layered over what appears to be a hoodie. From there, she slipped into a leather-look mini skirt with pleats and a subtle flare. She accessorized the look with classic knee-high boots and a black leather shoulder bag with grommets. Outfit credits weren't available at press time, so there's still a chance she snagged them on her recent Zara shopping spree. Still, it's an obvious departure from the low-rise jeans and It sneakers she sported a few days before.

Her brunette hair was curled into soft waves for the occasion and her makeup showcased a soft smoky eye paired with brown lipstick. Bennett, meanwhile, dressed casually in light wash jeans, a collared black jacket, a baseball cap, and white sneakers.

In case you're curious, Bennett's day job—when he's not dating supermodels such as Gigi Hadid—is directing music videos for rappers including Drake, Lil Yachty, and Eminem. He's also the founder of Lyrical Lemonade, a multimedia company that grew out of a blog he started in high school. In other words, this guy seems very well-connected. Plus, he and Gerber have apparently been friendly for a bit.

In July, Gerber and then-boyfriend Austin Butler went on a double date with Bennett and Daisy Jones and The Six star Camila Morrone. But here's the kicker: Morrone and Bennett announced their split after two years of dating only a few days after that fateful night out with Gerber and Butler. Suffice it to say, Gerber and Bennett have history. But drama aside, I'm of the opinion that every woman has the right to a palette-cleansing hang. I'll definitely be keeping my eyes on these two—and whatever they wear on their next night out.