After 557 days as Miss USA, Cheslie Kryst’s reign ends soon. But she’s not done.
Cheslie Kryst — Miss USA 2019 — is the opposite of what the media wants you to think of a pageant winner.
Sure, she oozes with the style and confidence of the fictional “Miss Congeniality.” But unlike the movie, she’s not an FBI agent, she’s an MBA graduate and licensed attorney from the Charlotte area.
She’s not echoing calls for “world peace,” but she is actively lending her voice and support to the Black Lives Matter movement.
And she’s helping women “dress for success,” both through charitable organizations and her own personal blog.
Due to COVID-19, Kryst will have held the Miss USA title longer than any prior winner (557 days). She also finished in the top 10 of the Miss Universe pageant in 2019. She’ll crown the next Miss USA on Nov. 9, and CharlotteFive sat down to talk to her about what she did throughout her extended reign.
“I’m excited to crown the next Miss USA — really just to find out who the next Miss USA is going to be, because beyond being Miss USA, I really am just a huge pageant fan,” Kryst said. “You get to see the pageantry of it all — pun intended.”
From Oprah to football, these memories stood out the most
Kryst was first introduced to the world of pageantry from her mother, April Simpkins, who was Mrs. North Carolina US in 2002 — the second Black woman to hold that title.
“When she won, I was maybe 11, and that was meaningful to me,” Kryst said. “I remember sitting in the auditorium and watching her win and watching her clean up all these awards. And then, when I went to school, all my classmates started asking me for autograph cards from my mom.”
“I was in middle school, and I was in a really awkward stage,” Kryst remembered. “I didn’t have a lot of friends, I was a nerdy weird kid who just liked to read during class, and it was so cool that people knew my name because of my mom. And so from that moment, I knew I was going to compete at some point in time.”
Fast forward to now: Kryst is anything but “awkward” and “weird.” She’s still a nerd — but nerds are in.
“I think it’s cool now to be a nerd — I think that’s in, or I’m telling myself that it is, you know, one or the other,” Kryst laughed.
During her time as Miss USA, she had the opportunity to interview Oprah for “Extra,” and play football with Tom Brady to benefit Best Buddies.
“Interviewing Oprah is like — you have reached the mountaintop,” Kryst said. “She is so nice. I asked her for feedback and tips and pointers after the interview, and she was really cool.”
And while she’s interviewed celebrities on a national scale, she’s also enjoyed monumental opportunities on a local scale.
“I got to do the Gamecocks cheer in front of over 70,000 people during homecoming,” Kryst said. “It was incredible, because I remember being an undergrad and thinking, ‘I hope I get to do this one day,’ as I’m watching Olympians and NFL players go out there. That was a full circle moment for me.”
Now, before she turns over the crown, she’ll enjoy another noteworthy pageant experience. On Nov. 7, Kryst will host Miss Teen USA alongside Allie LaForce, who was Miss Teen USA in 2005.
“I was overjoyed when the Universe organization gave me the opportunity to co-host,” Kryst said. “I’m counting down the days.”
What’s next for this attorney-turned-pageant winner?
Kryst will continue to work full time at ”Extra,” an Emmy-winning syndicated series showcasing celebrity and entertainment news. She will also work as a diversity adviser to Poyner Spruill, the North Carolina law firm where she was previously a member of the litigation team until she went on sabbatical to fulfill her Miss USA duties.
“These last couple of months have been so busy doing interviews, but I love it. I love the people that I get to work with and that it’s my job to talk to people,” Kryst said. “It doesn’t even feel like work.”
Kryst is looking forward to continuing to serve as a global impact ambassador for Dress for Success, an organization dedicated to helping women achieve economic independence through its suiting program, resume review, mock interviews, financial literacy classes, job training and more.
“I love working with the organization, and I’m glad to continue with them,” Kryst said.
She will also serve on the board of Big Brothers Big Sisters of America.
She wants real change. And she’s social about it.
Kryst not only uses her personal time to help those in need, but also to share her voice on her personal platforms about important social and political topics.
When you visit her Instagram, you’ll find more than just fashion photos. She’s shared posts about Junteenth, Black Lives Matter and the removal of Storm Thurmond’s name from the wellness and fitness center at the University of South Carolina.
Kryst has also moderated panels, such as the recent Social Justice Now Film Festival, which was co-headlined by Opal Tometi, human rights activist and co-founder of Black Lives Matter and actor/producer Michael B. Jordan.
“I did an Instagram Live on the official Miss USA account with Opal Tometi, who was one of the co-founders of Black Lives Matter. When in history would we have been able to do that before? It was exciting for me, because I was like, ‘Finally, this is our moment! I’ll show you what pageant girls are supposed to do, and this is it,’” Kryst told the Charlotte Ledger’s Cristina Bolling, who has been covering Krsyt’s journey.
Aside from her social media platforms, Kryst also has a personal blog called White Collar Glam — and if you’re a woman who works in a corporate setting (outside of COVID-19), you’ll want to check it out.
She started the blog when she graduated from law school, but the idea for it came to her when she was in a national trial competition.
“I brought three suits for this four-day competition and destroyed all three while I was there,” Kryst said.
Her trial coach quickly offered to drive her to Brooks Brothers to replace her outfits, but she knew the store was expensive and didn’t know where else to go locally since she was out of town for the competition.
“I want to be the help for someone else. I want to be the website that you look to when you need to know where to go shopping for these things, how to style them, what’s appropriate for the workplace and current trends. I wanted to be the answer to those questions that many women have,” Kryst said.
When in law school, Kryst wrote a final paper about how standards of modesty more acutely affect women, especially in the workplace. Her research even led her to lawsuits that had been filed about what women were wearing in the workplace.
White Collar Glam offers practical advice for working women, with articles outlining whether it’s appropriate to wear slingback shoes to work, staple items to have in your wardrobe, outfit inspiration and more.
“I think women are critiqued more often than men and there’s more room for error when it comes to picking out what we want to wear to the office,” Kryst said. “There’s a lot of questions that have to be answered, and I was glad to start that with my blog.”
Kryst is a force to be reckoned with — she’s not just a pageant winner, but an inspiring, intelligent woman dedicated to lending her voice to causes she cares about.
She’s living proof that you can enjoy both academics and pageants. And that it’s OK — what matters most is remembering to be unique.
“Be great,” Kryst said. “There are so many people who want to put women in a box and say, ‘You can be pretty, or you can be smart, or you can be athletic,’ and refuse to allow us to be multi-dimensional people.”
“Be who you want to be, whether that’s a swimsuit model who’s a graduate from an MBA school or a bookworm who wants to live a conventional life,” Kryst said. “Whatever it is, be brave and don’t allow people to judge what you’re doing.”
This story was originally published November 9, 2020 at 2:15 PM.
