When Biggie mentioned the ladies in the place with style and grace, I'm pretty sure he was talking about Ryan Destiny.
The actress was awarded the International Women of Power Event earlier this year for her ability to slay each and every damn day, and according to her, this 24-year-old style icon is just getting started.
After starring in Lee Daniel's hit show, STAR, Ryan made her mark in the entertainment industry as someone to look out for, and now, even after the show's recent cancellation, she has remained booked and busy. It was recently announced that Ryan was cast for a recurring role on the Freeform show, Grown-ish, as an HBCU transfer student who comes to shake things up for Zoey's gang at Cal U. And so far, the future is looking pretty bright for this fashionable young firecracker.
We stan for a cutely covered queen with melanin to boot, and Ryan's timeless style is well-deserving of our "yassss". If you're still not convinced that this Michigan-born fashion maven isn't the queen of all things style, I guarantee that the ten photos below will change your mind expeditiously.
Ryan is dripping nothing but sauce all in the atmosphere in this high-end Elisabetta Franchi knit fabric dress.
Sis looks like a whole bag of money in this iconic oversized blazer set by House of Holland.
On Wednesdays, we wear pink. But if you look as good as Ryan in this monochrome pant set, everybody in the room will be dying to sit with you.
John Parra/Getty Images for Revolt Music Conference
While I'm over here trying to pick out some elaborate outfit for date night, Ryan Destiny is out here snatching edges in a blazer and some boots. This blue printed piece from Off-White is just as versatile as her iconic wardrobe.
Melanin plus monochrome equals the ultimate drip. Ryan was royal AF in this purple on purple ensemble from New York design studio, AREA.
Giving us big Josephine Baker energy, Ryan served up this vintage look in a pair of Loriblu luxury Italian sandals.
Ryan is a whole mood in this silver two-piece ensemble, showing just enough skin to give this timeless look a little bit of an edge.
This look is serving up simple but significant, sassy but sophisticated. Ryan is the queen of looking blazing in a blazer, and this cropped suit is no exception.
Featured image by Ryan Destiny/Instagram
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The “Waterfalls” singer also revealed that since dating her beau, she no longer has a fear of marriage. “I do not. I don't have any fear at all when it comes to him,” she said. “It is just the way he is as a man, you know? He is a good guy. He has an amazing heart, and I mean, he checks off all of my list except for a few I don't know yet—’til we get married.”
Chilli and Matthew's relationship may be taking another significant step in the future. In a 2023 interview with ET, Matthew shared their potential plans for children. "That's the game plan. That's what we're trying to do," he disclosed. This news is particularly exciting as Chilli already has a son named Tron with music producer Dallas Austin, and the prospect of expanding her family adds a new dimension to her relationship with Matthew.
While Chilli is known as a legend in music, her dating life often takes center stage. But that’s what happens when you’re linked to some powerful men. Here’s a look back at Chilli’s dating history.
Dallas Austin
The “No Scrubs” singer dated the super producer throughout the ‘90s, and he produced many songs for her group, such as “Creep” and “Ain’t 2 Proud 2 Beg.” The two welcomed their son in 1997 and shortly parted afterward. Their relationship was documented in the VH1 TLC documentary Crazy, Sexy, Cool.
Usher
Usher and Chilli
Photo by Frazer Harrison/Getty Images
Usher and Chilli are probably each other’s most famous relationship. The former couple, which is still talked about to this day, were together from 2001-2004. They were still in touch over the years, but the “Unpretty” artist said she finally stopped all contact 15 years later.
Floyd Mayweather Jr.
Chilli and Floyd Mayweather Jr. sparked dating rumors after he appeared on her VH1 reality TV show What Chilli Wants in 2010. While the two looked really chummy on the show, the “Diggin On You” singer denied that they were ever romantically involved.
Nick Cannon
In 2016, Chilli and Nick Cannon were rumored to be dating. The Masked Singer host gushed about the mother of one in an interview with E! News. "She's amazing," he said about Chilli. "She's an outstanding person, but you gotta ask her what's going on." He later clarified that they were friends and he’d “be so lucky to be able to...be called dating someone like that."
Matthew Lawrence
Chilli and Matthew Lawrence have been together since 2022, and they sometimes give us glimpses into their relationship on social media. We can’t wait to see what the beautiful couple has in store for the future.
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Feature image by John Parra/Getty Images for Sandals Resorts
