Undress Any Celebrity

Full archive of her photos and videos from ICLOUD LEAKS 2024 Here

Aoki Lee Simmons kisses her much older boyfriend restauranteur Vittorio Assaf during their romantic St Bart’s vacation.

The 21-year-old model – daughter of fashion designer Kimora Lee and mega-music executive Russell Simmons – packed on the PDA with the 65-year-old co-founder of NYC’s Serafina restaurant chain.

Instagram:
(@aokileesimmons) Instagram photos and videos

Despite their 44 year age gap, the unlikely couple seemed to be happily in love, with Aoki showing off her flawless figure in a tribal print bandeau bikini. Her Italian beau was shirtless and sported light blue swim shorts with a chunky silver necklace.

Assaf, who has a history of dating much young women, seemed enamored with the lithe stunner – a beauty with brains who attended Harvard University when she was aged just 16. She posed as Assaf took snaps with his cellphone and they cooled off with a dip in the clear blue water before sharing a steamy smooch on the idyllic white sand.

Last week, Aoki shared some photos on social media from their trip to the sundrenched Caribbean island, curiously leaving her older boyfriend out. “Girls (possibly mermaids!) on film,” she captioned a carousel of pictures of herself posing in a bikini near a huge rock.

Assaf made headlines in 2021 when his now-ex-wife, former model Charlotte Bonstrom, left him after having an affair with her twin sister’s ex-husband, Thierry Gillier.