Aoki Lee Simmons made a splash on the red carpet as she was joined by her mother and sister for the 25th Anniversary Smile Train Gala on Wednesday evening.
The 21-year-old model looked effortlessly chic at the New York City event with her youthful-looking mother Kimora Lee Simmons, 49, and her older sister Ming Lee Simmons, 24, at her side.
Aoki’s public appearance marked the first time she had been spotted since her shock split from her much-older boyfriend, the 65-year-old restaurateur Vittorio Assaf.
The two reportedly ended their May–December romance in early April, just days after they were revealed to be a couple when they were seen kissing on the beach during a holiday to St. Barts.
The rising model and her family arrived at Cipriani 42nd Street to show their support for Smile Train, a nonprofit organization that works to provide surgeries to repair cleft lips and palates, while also training local doctors across the globe to perform the surgeries.
Aoki Lee Simmons, 21, was joined by her mother Kimora Lee Simmons (L) and sister Ming Lee Simmons (center) at Smile Train’s 25th Anniversary Gala on Wednesday in NYC
The family appearance marked the first time Aoki has been seen since she was reported to have split from her much older boyfriend, the 65-year-old restaurateur Vittorio Assaf; pictured April 2 in St. Barts
Aoki showcased her slender figure with her little black dress, which featured long long sleeves and a floppy black satin bow over her chest.
The look stopped at the top of her thighs, putting the spotlight on the 5ft11in model’s long legs.
She covered them with black tights and wore classic black pumps with slightly pointed toes and straps that wrapped around her ankles.
Although she had been rocking gorgeous voluminous curls in recent days, Aoki opted for a reserved look by tying her hair back tightly while parting it down the middle, which highlighted her tastefully made-up face.
She completed her ensemble with a thick, shimmering diamond-encrusted bracelet.
The magazine star was joined by her mother Kimora, who shares Aoki and Ming with her ex-husband Russell Simmons, whom she divorced in 2009.
Kimora flashed her fit arms in her dress’ sleeveless black bodice.
The top featured a slanted waistline and connected to a glittering silver skirt that lit up the red carpet and featured a sky-high slit to prominently feature her toned legs.
Aoki showcased her slender figure with her little black dress, which featured long long sleeves and a floppy black satin bow over her chest
The look stopped at the top of her thighs, putting the spotlight on the 5ft11in model’s long legs
She wore black tights and classic black pumps with pointed toes and straps around her ankles. Her mother Kimora wore a dress with a sleeveless black bodice and a glittering silver skirt with a sky-high slit
Ming was the spitting image of her mother, and she stunned in a sleek black dress that hugged her curves
The look featured a slim cutout over her chest which showcased her cleavage
Smile Train and its mission to help those suffering from cleft lips and palates has been a major issue close to Kimora’s heart
Kimora wore matching silver open-toe heels and wore her lustrous raven tresses down over her chest in thick waves.
Ming was the spitting image of her mother, and she stunned in a sleek black dress that hugged her curves.
The look featured a slim cutout over her chest which showcased her cleavage, and the dress featured crisscrossing black straps that wrapped around her torso and allowed her to adjust the size of the cutout.
She styled her hair straight like her mother’s, and she complemented her outfit with a pair of strappy black open-toe heels.
Inside Cipriani 42nd Street, Aoki was spotted catching up with fellow model Brooks Nader.
Smile Train and its mission to help those suffering from cleft lips and palates has been a major issue close to Kimora’s heart.
Last year, she traveled to Lima, Peru, to support the organization’s efforts and to meet some of the patients who had benefited from the surgeries.
Cleft palates occur when the roof of the mouth opens up into the nose, while individuals with a cleft lip have an opening on their upper lip that reaches into the nose. The conditions can occur in conjunction or separately, and they can be life threatening.
Last year, Kimora traveled to Lima, Peru, to support the organization’s efforts and to meet some of the patients who had benefited from the surgeries
Kimora, who is a Smile Train Ambassador, was honored at the organizations 25th anniversary gala with the Goodwill Ambassador Award, so it was fitting that her daughters would honor her
Aoki and Ming were both pictured grinning ear to ear as they took to the stage to sing Kimora’s praises at the podium before presenting her with her award
Kimora pictured with Brooks Nader at the gala
Cleft palates and lips can be dangerous for affected child — and older individuals — as it can make feeding difficult. Affected individuals may also have difficult speaking, and they can develop frequent ear infections and have hearing problems.
Kimora, who is a Smile Train Ambassador, was honored at the organizations 25th anniversary gala with the Goodwill Ambassador Award, so it was fitting that her daughters would join in the festivities to honor her.
Aoki and Ming were both pictured grinning ear to ear as they took to the stage to sing Kimora’s praises at the podium before presenting her with her award.
Last month, Aoki and her boyfriend Vittorio Assaf were reported to be ‘100 percent done’ not long after thy seemingly confirmed their shock romance during a getaway to St. Barts in early April.
The news of the separation came after both her mother Kimora and father Russell gave their reactions to Aoki sharing a kiss with the 65-year-old restaurateur during the relaxing trip.
A source told Page Six of the pair’s romance: ‘It’s 100 percent done. They’re absolutely not dating.’
However, had referred to Assaf as her ‘boyfriend’ in Instagram Live reels while in St. Barts.
The insider, who is close to Aoki, stated that she said on Monday: ‘”Of course, I’m not with him. I was never with him.”‘
Aoki split from Vittorio Assaf, 65, in early April, just days after they confirmed their relationship with a kiss in St. Barts. An insider who is close to Aoki claimed that she said: ‘Of course, I’m not with him. I was never with him’; seen in November 2023 in NYC
They also informed the outlet that the beauty is not materialistic and such claims were ‘absurd.’
‘She’s not even like that. 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,’ they said.
A separate insider explained that Vittorio is an ‘older man with little boy charm.’
‘He’s always loved younger beautiful women. He’s gotten older, but his taste hasn’t changed,’ they claimed. ‘I wouldn’t be surprised if he’s out with another young girl tonight!’
During the tropical vacation, Aoki had filmed herself while inside Assaf’s home on the island and gushed, per Page Six, ‘I’m the happiest person to ever happy right now.’
She also gave a glimpse of the restaurateur’s shoes and said, ‘Look at how huge his shoes are. That makes me really happy. He’s [6-foot-4].’
Earlier in April, Aoki and Vittorio were spotted spending time on a beach together and at one point, shared a kiss on the sandy shore.
The pair also enjoyed a picnic together and Assaf was seen taking a few photos of the model as she struck poses for the camera.
The two seemingly confirming their romance sparked a fierce viral debate about age gaps in relationships and how much is too much as Aoki is young enough to be Vittorio’s granddaughter.
A separate insider explained that Vittorio is an ‘older man with little boy charm’
Earlier in April, Aoki and Vittorio were spotted spending time on a beach together and at one point, shared a kiss on the sandy shore
Her father, Russell Simmons, soon broke his silence on his dating Vittorio. ‘I’m not gonna kick and scream about her choices,’ said the Def Jam mogul to TMZ on Monday.
The former husband of Aoki’s mother, model and designer Kimora Lee Simmons, added: ‘All I can do is offer my advice and unconditional love.’
Russell also said his daughter warned him of her romance a day before the photos surfaced.
Russell and Kimora were wed from 1998 until 2009. Aoki is Kimora’s youngest daughter she shares with her first husband. She also shares daughter Ming, 24, with Russell.
She has other kids, too: The fashion designer shares sons Kenzo, 14, and Wolfe, nearly nine, with exes Djimon Hounsou and Tim Leissner, respectively. With Leissner, she adopted her son Gary, 14, in 2020.
Kimora notably reposted a since-deleted video of a mother panda furiously pulling away her baby cub with her teeth and wrote: ‘On my last nerve right now!’
Assaf is a known New York City personality. He owns the Serafina Restaurant Group.
He grew up in Milan, Italy where he studied hard: first with a degree in Political Science then he studied Law at the University of Urbino.
Assaf spent eight years on the floor of Milan’s Stock Exchange then came to New York in the eighties. He also opened Café Candiotti in 1985, which became a hot spot and now runs the Serafina Restaurant Group.
It is not known how long she and the restauranteur have been romantically involved, but a source close to the model revealed to People that the pair had met while vacationing in St. Barts.
‘Aoki and Vittorio are spending time together and enjoying each others’ company,’ the insider told the outlet.
The couple both took to Instagram to share snaps from their vacation but did not post any photos of each other.
Last week Aoki talked exclusively to DailyMail.com but did not mention her new lover.
Simmons was modeling for BCBG New York, bringing her all to the visuals for the Spring Summer 2024 capsule for BCBG Group.
Her father, Russell Simmons, soon broke his silence on his dating Vittorio. ‘I’m not gonna kick and scream about her choices,’ said the Def Jam mogul to TMZ
Kimora notably reposted a since-deleted video of a mother panda furiously pulling away her baby cub with her teeth and wrote: ‘On my last nerve right now!’
Russell and Kimora were wed from 1998 until 2009. Aoki is Kimora’s youngest daughter she shares with her first husband. She also shares daughter Ming, 24, with Russell; Kimora and Aoki seen in November 2023 in L.A.
In regards to modeling, Aoki said, ‘My goal is to learn and grow as I navigate my own path through this business, and have a lot of fun doing it’
In regards to modeling, Aoki said, ‘My goal is to learn and grow as I navigate my own path through this business, and have a lot of fun doing it.’
When asked how mom has inspired her, she answered: ‘Let me count the ways! Honestly, there are so many things that I look up to her for, but if I had to pick one it might be her ability of self-reliance.
‘She has a confidence that even if she doesn’t know the answer to something right now, she knows how to figure it out. That’s inspiring.’
As far as plans to design one day she said: ‘Never say never, but perhaps just not yet.’