Setting her sights

People Style

November 4, 2019

Miss USA Cheslie Kryst is busting pageant stereotypes — and showing that women really can do whatever they set their minds to.

By Cathy Martin
Production + Wardrobe: Whitley Adkins Hamlin | The Queen City Style 
Photographer: Richard Israel
Makeup: Josiah Reed  •  Assistants: Kiley Copps and Savannah Harris

On a late-summer morning, Cheslie Kryst breezes in ready for make-up, dressed like a typical 20-something — sneakers, ripped jeans, black tank top and a satin bomber jacket, her distinctive curls trailing behind her. But as this daylong photoshoot — which includes a few of Cheslie’s former Charlotte hangouts — gets underway, it becomes clear there’s nothing typical about this 28-year-old pageant queen. 

Cheslie, who was born in Jackson, Mich., but moved to Charlotte when she was 4, wowed both viewers and judges back in May when she was crowned Miss USA in Reno, Nev., the third woman from North Carolina and the oldest ever to win the title. Her interview responses about the importance of fostering inclusivity and diversity resonated with the audience. Since then, her life has been a whirlwind of travel, photoshoots, interviews and public appearances. 

The word “overachiever” often comes to mind while listening to Cheslie talk about her accomplishments and current projects. An associate at Poyner Spruill LLP practicing complex civil litigation (she’s currently on leave to fulfill her duties as Miss USA), Cheslie somehow finds time to write a weekly fashion blog, prepare for the launch of her own fashion line for working women, and volunteer with Dress for Success, a national nonprofit that provides support and professional attire to help women secure jobs and achieve economic independence. As SouthPark was making the final edits to the November issue, Cheslie added a new bullet to her resume: In early October, she joined ExtraTV as a correspondent in New York City, where she currently lives. Already, she’s aired segments alongside superstars Lizzo, Terrence Howard, Millie Bobby Brown and Zendaya.

Dundas Deep V long-sleeve lame gown, Capitol, $5,460; Marion Parke ankle-strap heel, Capitol, $650; on location at The Duke Mansion

Pageants are in her blood, so to speak: Her mother, April Simpkins, was crowned Mrs. North Carolina U.S. in 2002. “I just remember thinking, she was a superstar, she was a celebrity — she was my hero,” Cheslie recalls. “I remember her having a voice, and I remember people listening to her, and I wanted that kind of influence.”

Growing up, though, winning pageants wasn’t the only thing on Cheslie’s mind. After attending elementary and middle school in Charlotte, she moved to Rock Hill, S.C., with her mom and five siblings after her parents got divorced and her mom remarried. About a year later, the family moved again to Fort Mill, where she graduated from Fort Mill High School. From there, Cheslie enrolled at the University of South Carolina, where she was in the Honors College and a Division 1 athlete as a member of the varsity track and field team. Graduating with a business degree, she came back to North Carolina, earning MBA and law degrees from Wake Forest University. She joined Poyner Spruill in 2017.

Through it all, Cheslie competed in pageants, including two attempts at Miss North Carolina in the Miss America organization (finishing once in the top 10, the other time as first runner-up). Switching to the Miss Universe organization, she competed three times for Miss North Carolina USA, eventually winning the title in October 2018. 

“I just knew the answer was always going to be no if I didn’t try,” Cheslie says about her repeated attempts at earning a crown. “The year that I competed as Miss North Carolina USA was my last year of eligibility. And I thought, I don’t want to get to the age of 40 and look back and think, if I could have competed, I wonder what would have happened?” she says. “I didn’t want that feeling of regret. I’ve had that feeling because I didn’t try or didn’t work hard enough or just didn’t give myself a chance. And I just didn’t want to feel that ever again.”

Ganni printed organza dress, Poole Shop, $350; Gucci GG Marmont black belt, Capitol, $650; Nili Lotan ribbed turtleneck, Poole Shop, $375; SPRWMN leather leggings, Poole Shop, $1,325; Ganni western ankle boots, Poole Shop, $505; Stiebich & Rieth oval black crossbody bag, TRC W, $1,295; Addison Weeks Graves gemstone cuff, $228; on location at Amelie’s French Bakery & Café, Park Road Shopping Center

Until 2017, Miss Universe contestants were required to be under 26 years old to compete. That year, the organization increased the age limit to 28. (Cheslie was 27 when she won the Miss North Carolina USA title last year.) 

In fact, competing as an older contestant with a little more education and work experience under her belt behind her might have given Cheslie an advantage. While both the Miss USA and Miss America pageants originated as swimsuit competitions, priorities have changed, Cheslie says.

“Nowadays it’s very different — the focus is not just on what you look like but can you be a good role model and representative for other people,” she says “And there’s no reason why a woman who’s older than 24 shouldn’t be able to do that.”

Given the origins of beauty pageants, it’s not surprising many people still write them off as superficial. While Cheslie has received overwhelming support from her fans — she has 125,000 followers on Instagram alone — there are also critics. 

“Some are people saying, ‘Why are we still doing pageants, I don’t understand? Aren’t we objectifying women?’ I think it’s because many of those people haven’t watched and don’t really understand the platform that being in a competition like Miss USA gives you,” she says. “Every single woman from the top 10 of Miss USA this year had a minute-long video, where we just talked about anything we wanted to. How many people have that platform? You’ve got a chance to be on television in front of millions of people.”

With her new exposure, Cheslie has two particular goals. The first is bringing more attention to Dress for Success, a program about which she is passionate. Second, she wants to continue speaking to audiences about criminal-justice reform. “I worked for pro bono clients who have received excessive sentences, typically for low-level drug crimes, and I think that’s wrong, I think that’s unjust, and I think it needs to change,” she says. “That and other issues need to be reformed, and I hope to continue to shed light on that.”

Spiritual Gangster high-waist leggings, Neiman Marcus, $118; Spiritual Gangster Shakti Brami side-striped crop top, Neiman Marcus, $78; Nike sneakers, Neiman Marcus, $150; on location at the Dowd YMCA

Being in the spotlight has led to other professional opportunities as well. Earlier this year, she was invited to attend the annual conference of the Council of Chief Justices at Biltmore Estate in Asheville, where she gave a fireside chat along with Cheri Beasley, chief justice of the North Carolina Supreme Court. Among the topics they discussed were understanding generational differences in the workplace. 

But with the celebrity also comes responsibility.

At a fundraising event at SouthPark mall back in June, Cheslie posted a photo of herself with a young fan on her Instagram page. The caption read: “The smallest little eyes watch you more closely than any others. The responsibility to be a positive role model for precious little girls like this one is a constant source of motivation for me. I hope she grows up believing the possibilities for her future are limited only by the depth of her own imagination.”

What exactly is her message to young girls who might be watching?

“I want to tell them to be brave and be bold. Because nowadays, I think more than ever, there are people who want to give guidance to people, but they’re not always open-minded. There are a lot of people who have a one-track mind about what a woman can do.” 

She cites an example of how people subconsciously associate certain roles with males or females. 

“I remember there was a time when I was talking to somebody about a judge who made a ruling on a motion I had. They said, ‘What did he say after that?’ Well actually, the judge was a woman. 

“I want young girls to understand that regardless of the tunnel vision that many people have in thinking women can’t have professional careers or can’t advance into leadership roles — regardless of those perceptions and thoughts — women actually can do what we put our minds to, and we can — if we push hard enough — achieve really whatever we want.”

Peserico denim stripe double-breasted jacket, TRC W, $1,095; Peserico denim stripe pant, TRC W, $625; Lis Lareida white cotton poplin blouse, TRC W, $350; Santoni tobacco suede bootie, TRC W, $795; Addison Weeks Starr gemstone studs, $48; on location at Mecklenburg County Courthouse

Back in Charlotte, Cheslie gets a little nostalgic visiting Amelie’s, where her go-to order is a chai tea latte and cotton-candy macarons, and the Dowd YMCA, where she reflects on her old routine of taking 5 a.m. fitness classes on the rooftop deck overlooking the city. 

“I do love New York. It’s fast-paced — I feel like that matches my personality — but I think [I just miss] the familiar places I used to go in Charlotte,” like Nikko’s in South End where she and her mom enjoyed sushi. Much of her family lives in the area too, including her parents, her grandmother and most of her siblings. 

Next month, Cheslie will contend for the title of Miss Universe, competing against more than 90 candidates from across the globe. Sometime after that, she plans to return to her law office at Poyner Spruill in downtown Charlotte. When I ask her about family — after all, she comes from a large one — she says she’s keeping things open. 

“I think that growing up, society places so many undue expectations on people — not just on women, but [on] men and women. … People always think that life is supposed to go in a straightforward progression, but I disagree,” she says.

“I’m just kind of going with the flow, and waiting to see what comes up.” SP


Stylist Whitley Adkins Hamlin asked Cheslie Kryst to describe her personal style. Comments were edited for brevity.

How has your personal style evolved over time?
My style is classic but with a modern twist. I think there were times I thought I needed to keep up with today’s trends, but then I sort of came into my own. There is still an element of modernity in the way I dress now, but for the most part I would describe my style as very, very classic. 

What is your outfit of choice? 
I think as an attorney I have just grown accustomed to wearing suits. We are experiencing the resurgence of the suit, and there is truly a suit for every occasion — whether I’m going into the courtroom or to a fashion show or brunch. I have a suit that I love that is shorts instead of pants. It is something you can wear to a more casual event, but it is still classic and modern.  

How have pageant styles changed since your mom was
Mrs. North Carolina U.S. in 2002?

I think we’ve lost a lot of shoulder pads. What’s interesting is that I wore a lot of my mom’s gowns. She has a very classic black velvet gown that has a beaded neckline with dangling crystals that I wore when I won my first competition. Some of the designs were very timeless and classic. 

Whose personal style do you admire and why?
Olivia Pope, [the character played by Kerry Washington] on the television show Scandal. She would always wear feminine pieces, but she didn’t sacrifice power. Her style on that show is a mix of femininity and power all in one. 

What is the mission of your fashion blog, White Collar Glam?
I started my blog because I had a tough time finding professional clothing that I could afford and that was appropriate for my work. I wanted to share the answers to so many of my own questions I knew other people also had.  

Have you always loved fashion? 
Not necessarily, but I always liked being able to design my own look. When I was younger, I shopped at Goodwill. My grandmother gave me a sewing machine, and I would change and alter the clothes to have my own look. I have always enjoyed the creative side of fashion. 

What advice would you give to young girls about what
to wear? 

You don’t have to wear something just because everyone else is wearing it. There are a lot of trends, but you don’t have to adopt them just because others are. I think what’s most important is for girls to find their own sense of style and be true to that. Wear what you feel like speaks your own personality, what speaks to your own self, and what you want to share with others.  SP

Header image: Dundas deep V cape halter gown, Capitol, $4,990; Nicholas Kirkwood Leeloo strappy sandal, Capitol, $675; on location at The Duke Mansion

Car service provided by Rose Chauffeured Transportation

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