Aoki Lee Simmons, 21, and Restaurateur Vittorio Assaf, 64, Debut Romance With Beach PDA

Aoki Lee Simmons and restaurateur Vittorio Assaf debuted their romance by packing on the PDA during a trip to St. Barts.

Simmons, 21, and Assaf, 64, were spotted on Tuesday, April 2, kissing on a beautiful beach in the Caribbean, according to photos obtained by Page Six. The Serafina co-owner then took photos of the model as she posed in the sand before they took a dip in the ocean together.

A source confirmed the pair’s relationship to People on Friday, April 5, saying they’re “enjoying each others’ company.”

Simmons shared photos from her tropical trip via Instagram but conveniently left her new beau out of the snapshots.

Aoki is the youngest daughter of model and mogul Kimora Lee Simmons, 48, and entrepreneur Russell Simmons, 66. Assaf, for his part, hails from Milan, Italy, and has been a staple in the New York restaurant world since cofounding Serafina Restaurant Group.

Aoki recently spent time in Assaf’s hometown, attending her first Milan Fashion Week in February. She documented the experience via Instagram and walked the runway for Philipp Plein, Monse and more.

While Aoki began modeling at a young age through her mother’s brands, Baby Phat and Just Fab, she focused on her career full-time after graduating from Harvard University at age 20 in June 2023. She relocated to New York City and has spoken openly about her life path.

In August 2022, Aoki had a lengthy response to a fan who commented on one of her TikTok videos, “You’re so articulate and obviously educated .. how come u chose modeling?”

In addition to simply loving to model, she called the career her “creative passion.”
“Well, one, models aren’t uneducated and not articulate, but two, I think what you’re really getting at is, ‘Why am I going into a field that doesn’t necessarily require a degree or require a whole lot of book smarts when I have a lot of education?’” she said via TikTok. “Well, one, because I love it, and I think we should normalize liking something. You don’t have to do what you’re immediately good at.”

Aoki said she hopes “women aren’t being asked this question” as time goes on.

“Like, not being asked, ‘Why did you follow your more creative passion even though you’re smart?’” she continued. “I would like to change the idea that you can’t be smart and pretty, or you can’t be smart and enjoy your looks or enjoy a creative, beauty- [and] fashion-based career. You can be two kinds of people in one person.”