Aoki Lee Simmons, 21, attended the Columbia Law Gala in New York City with her friends after enjoying a St. Barts getaway with her much-older boyfriend Vittoria Assaf, 65, earlier this week.
On Sunday, the daughter of exes Kimora Lee Simmons and Russell Simmons took to Instagram to share photos at the event alongside her pals.
In the snaps, her boyfriend Assaf, was not seen as the day before her parents seemingly responded on social media about her jetting off with her new love — who is 44 years her senior.
Seemingly paying no mind to the backlash over their age gap and PDA-filled vacation snaps, she appeared to be in high spirits as she modeled a slinky pink dress in snaps alongside Molly Martinez, one of her friends from her time studying at Harvard University before she graduated in 2023.
The model showcased her trim physique in the cowl-neck, satin gown with feathers trailing up her skirt.
She threw up her bouncy curls into an effortlessly stylish ponytail and opted for sultry makeup featuring sharp eyeliner and a wine red-colored gloss.
In contrast against her feminine-styled dress, she added a touch of edginess by carrying a black handbag and sporting chunky platform boots.
Her outing with her college friends comes after she enjoyed a romantic trip to St. Barts with Assaf.
During their vacation, she confirmed her romance with the restauranteur as the pair were seen locking lips on the beach during their sun-soaked getaway.
It is unclear how long she and Assaf have been romantically involved, but a source close to the model revealed to People that the pair had met while vacationing in St. Barts.
As the pair enjoyed their couple’s getaway at what is reportedly a favorite destination for the Simmons family, the Serafina restaurant chain co-founder was taking photos of her and documenting their day at the beach.
The couple both took to Instagram to share snaps from their vacation but did not post any photos of each other.
However, on the last day of their trip, fan-taken footage from Simmons’ Instagram Live showed the couple interacting on camera.
After going live on the app, she reportedly referred to Assaf as her ‘boyfriend’ and displayed what social media users called ‘bizarre’ behavior.
‘Last day in St. Barts. I’m so sad but I’m very happy,’ she said during her Instagram Live. ‘When I return home, everyone who knows me will be getting a happier, more chilled out version of me.’
The Serafina co-founder did not appear in the video but could be heard talking off-camera.
‘Would you like to share your favorite thing about the trip?’ Simmons asked him at one point.
When he answered, she giggled: ‘He said me.’
An insider previously told People that despite her parents’ opinions, ‘Aoki and Vittorio are spending time together and enjoying each others’ company.’
James Parker is a UK-based entertainment aficionado who delves into the glitz and glamour of the entertainment industry. From Hollywood to the West End, he offers readers an insider’s perspective on the world of movies, music, and pop culture.
