‘You’re Not Pretty Enough’: Aoki Lee Simmons Ditches Modeling After Breakup with 65-Year-Old ‘Sugar Daddy’ and Comparisons to Mom Kimora

Following your dreams can sometimes be a difficult feat, even for nepo babies. 

Aoki Lee Simmons has been admittedly having a rough time thriving in the modeling industry like her mother Kimora Lee Simmons once did.

The 22-year-old went to social media to air out her woes, claiming that higher-ups in the industry have been criticizing her for her looks

Speaking to her social media followers in a reposted Oct. 11 video, Aoki said, “I love modeling but it’s hard to go somewhere and get told over and over and over over, no, no, no you’re not pretty enough, you’re not pretty enough.”

The youngest daughter of music mogul Russell Simmons made history as one of the youngest Black women to graduate from Harvard University, which she began at age 16. She claims she will soon be “wrapping up modeling soon” and putting her degree to use.

“I’m getting a job in my degree field. But you know while I’m still here I should do my best,” Aoki added. 

Trying to get her followers to understand her reasoning, she further explained, “If I’m going to a casting that my mom always got and I feel like it just feels like one big fat, like, comparison all time. … Like, I get that my mom is always going to be a way better model than me. But it’s just annoying to have that comparison sometimes.”

“‘It must be so great to go to a casting that your mom did,’ and I’m like, ‘No, it’s not. It’s awful, because then when you don’t get it it feels even more like …’” she stopped without finishing. “I think I’m going to end up switching back to working in government, which is what my degree’s in. But while I’m here I’m going to do my best, OK.”

It’s not clear what social app Aoki was speaking to her followers on but someone seemingly suggested that she get a coach in order to help her get more gigs.

But she rejected the offer saying, “I don’t need a coach, I’m a good model. I know that sounds like conceited, but it’s not. I worked really hard at it. It’s just it’s a hard industry. Like, there are a lot of beautiful great girls, great models, who don’t have a job.” 

But Aoki has her plans for the future laid out. She said, I”m taking the foreign service test so I can get back into international relations which is what my degree is in. You should finish out strong and finish out with respect to the job and the industry that you chose to be involved in. So I’m going to go finish strong,” something she later claims her mother always taught her. 

Aoki also updated fans about a gig with Victoria’s Secret she went out for ahead of the brand’s 2024 Fashion Show in New York City on October 15.

“I’m not walking Victoria Secret this year, no. I was maybe going to, but I didn’t get it. But I’m happy for everybody who did,” she noted.

Aoki’s dramatic career switch arrives months after she complained about having to get a job. She moved into her first apartment in New York City, which she furnished mainly by herself, following her breakup with 65-year-old Serafina Restaurant Group founder Vittorio Assaf.

The two made headlines after they were caught kissing in photos that spread like wildfire in April on a beach in Saint Barthélemy.

Fans immediately began to draw comparisons to her mother’s age-gap relationship to her father, Russell Simmons, whom Aoki previously warned she would need a “sugar daddy” if he did not raise her allowance.

Aoki hinted that her parents were concerned about her relationship with Assaf, who was 44 years older than her. Within weeks following criticism, she said I “doesn’t have a boyfriend” in an Instagram Live video and then turned off her comments.

Her mother Kimora began modeling around the age of 13 and shortly after landed a contract with Chanel and worked under renowned German fashion designer Karl Lagerfield. Kimora went on to marry the former Def Jam executive in 1998.

According to Russell, he met Kimora when she was 17 and they began dating she was 18, when he was in his mid 30s. After welcoming Ming and Aoki, they divorced in 2006.

Kimora is also well known for launching the iconic fashion brand Baby Phat, a sister brand to Russell’s Phat Farm. The launch took place in 1999 before she and Russell sold the brand to Kellwood Co. in 2004. 

This is also not the first time Aoki has expressed that she was getting picked on for her looks. At just the tender age of 15, she wrote a long message on IG revealing that she chose to start posting her face more after insecurity began to build from hearing repeatedly that her appearance wasn’t as favorable as her mother’s and her older sister’s Ming Lee Simmons. 

She wrote, “I used to be very picky about pictures and not really show my face and would often not post pictures of cool events or important moments because I didn’t like my smile or I was standing next to my beautiful sister. It’s easy to get insecure when your sister and mom are models.”

Aoki continued, “I’ve dealt with a lot of negativity on Instagram, comments saying I’m not as pretty as my big sister (who is the best by the way). We all want to look nice in our photos but I’ve tried to let all of that go and just post pictures where I look happy or was actually having a good time. I try not to worry who I’m standing next to and just share good moments with you guys.”

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