Kimora Lee Simmons' Daughter Opens Up After Split From 65-Year-Old Beau In True Gen Z Fashion

When Kimora Lee Simmons' lookalike daughter Aoki Lee Simmons reacted to her split from Vittorio Assaf, she did it in a way that's true to form for the generation that can't leave the house without their Stanley cups. Apparently, what Aoki is sipping from her trendy tumbler these days is some blue brew.

Celebrity relationships with uncomfortable age gaps always garner a lot of attention, so 21-year-old Aoki became the tabloid topic du jour when she was photographed kissing 65-year-old Assaf during a trip to St. Barts. The model even had the sexagenarian restaurateur playing the role of her dutiful Instagram BF by getting him to snap pics of her posing in the sand. But just two days after images of their trip went viral, a source told Page Six the pair had parted ways. Aoki seemingly confirmed this with a mood update. "I'm depresso espresso," she wrote on her Instagram Story (via Page Six). Luckily for oldsters who never have any clue what Zoomers are talking about, Urban Dictionary is here to help. One popular definition of "depresso espresso" is "a fun way to say depression."

After seemingly addressing her breakup, Aoki did something else that's very Gen Z: she abruptly switched topics by giving fans an update on an unrelated saga. "But I did indeed have to share I FOUND WHERE ALL MY PACKAGES [HAVE] BEEN GOING TOO?" she added. Unfortunately, the internet wasn't ready to let Aoki change the narrative just yet.

In many of the online discussions about Aoki Lee Simmons' relationship with Vittorio Assaf, she's been accused of being a "sugar baby" who was only spending time with the wealthy Serafina founder because of the luxurious lifestyle he could provide for her. After the pair reportedly broke up, one Instagrammer commented, "Just a sugar daddy and a sugar baby. It's usually a short-term contract."

The gossip about the May-December romance also sparked renewed interest in Russell Simmons' damaged relationship with his daughter. In a resurfaced video posted on The Neighborhood Talk Instagram account, the music mogul got called out by Aoki for not paying her a high enough allowance. The footage of the father and daughter video chatting was filmed in 2022 while Aoki was still attending Harvard (she graduated in 2023). "If you don't raise my budget, I'm gonna get a sugar daddy," Aoki jokingly warns her incredulous father in the clip. However, Russell didn't take her plan to fund her lifestyle seriously. "You don't even have sugar daddy capabilities," he responds.

When TMZ asked Russell to share his thoughts about Aoki and Assaf's PDA pics, the Def Jam exec revealed that Aoki warned him they were incoming. "I'm not gonna kick and scream about her choices," he said. Russell couldn't complain without coming off as a bit of a hypocrite; per People, Kimora Lee Simmons was a 17-year-old model when Russell first met her — and he was 35.

During an Instagram Live, Aoki Lee Simmons spoke about Vittorio Assaf like he was more to her than a fling. While showing off his villa in St. Barts, she described him as one of two boyfriends she's had. She also bragged about Assaf buying her a bikini and a pair of sandals during their getaway. "I'm the happiest person to ever happy right now," she told her viewers. In another video, she was filming inside a vehicle as she and Assaf drove past a Bulgari store. "I am, though, a very big Bulgari person," Simmons said. After they passed the store, she told Assaf, "Hopefully they have my necklace when I come back and they don't sell it to somebody else."

Despite Simmons dropping a huge hint to Assaf that she wanted to stop and go shopping for jewelry at the luxury store, a source insisted that the model is no gold digger. "She doesn't care about jewelry. She doesn't have Hermes. It's not even her. She doesn't even care about expensive things like that. She's like more of a geek," the insider told Page Six. In a 2018 Instagram Live video, Simmons did describe herself as "low-maintenance" — before showing off the dozens and dozens of skincare products and cosmetics cluttering her bathroom counter, cabinets, and drawers. 9MagTV estimated its value to be around $20,000.