Members In Focus: Cheslie Kryst Knows the Beauty of Persistence

Photos by Blue Method Films

By Amber Nimocks

Cheslie Kryst failed to win the Miss North Carolina crown on her first attempt in 2014. It wasn’t bad for a first try, though. She cracked the top 10 and won a swimsuit award.

Before she went for the prize again in 2015, she prepared relentlessly: thousands of ab reps, countless hours at the piano playing Stevie Wonder’s “Don’t You Worry ‘Bout A Thing,” and endless hours watching and reading the news to be ready for the interview.

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She lost again. Runner-up. Plus a swimsuit award.

That was her last shot at the crown with the Miss America organization. She had aged out. But she still had a chance with the Miss USA organization.

So in the fall of 2016, she slipped into another stun­ning, sequined gown, strapped on another knock-out bikini and walked the stage once more in hopes of being crowned Miss North Carolina USA. Fourth runner-up. And the overall swimsuit award.

Firm: Poyner Spruill LLP, Charlotte office
Education: Wake Forest University School of Law and Graduate School of Business, University of South Carolina

“Success consists of going from failure to failure without loss of enthusiasm.” – Winston Churchill

This quote has been on a sticky note stuck to my computer monitor since I began practicing in 2017. I’ve come to realize that many of the successful people I know aren’t superhuman — they just kept going.


Returning in 2017, she knew it was her year, and she brought her “fiercest walk to the stage.” The judges gave her nothing. No top five. No swimsuit award. Zilch.

In a year marked by milestone achievements for Kryst, it was a glaring disappointment.

In the spring of 2017, she and her Wake Forest Law School trial teammates won the AAJ Student Trial Advocacy Compe­tition national championship. She also graduated from Wake Forest University School of Law, earning both a law degree and an MBA, passed the North Carolina Bar and landed an asso­ciate position in Poyner Spruill’s Charlotte office. In her free time, she launched a fashion blog aimed at working women.

Still, that crown eluded her.

“I had one year left until I reached the age limit for the Miss USA system,” she wrote. “I decided I’d rather compete my final year and lose than wonder for the rest of my life what could have been.”

Photo: Sage Media Group

Fifth time was a charm. She won the Miss North Carolina USA pageant in November and will compete for the Miss USA title this summer. Kryst says her involvement with pageants has informed her work as an attorney.

“In order to be competitive in a pageant, you need to be ac­complished, well-rounded, and service-minded,” she says. “In order to win a pageant, you have to be likeable, approachable, and friendly. It’s really similar to the practice of law and attract­ing the clients and business that you want. It’s not just about being competent and being able to do the work — you have to go a step further. You need to be a person who is easy to work with, receptive and open to questions, and client-focused.”

Kryst took some time recently to answers our questions about balancing her passions, her goals for her reign as Miss North Carolina and why the NCBA has been essential in her career so far.

Q: How did you get involved in pageant competition? What do you find most compelling about this pursuit?

A: I was inspired to compete in pageants by my mom, April Simp­kins, who was Mrs. North Carolina US 2002. I remember watching her win and going to appearances with her during her reign. She was involved in countless events because of her title — parades, speaking engagements, and I can’t even remember how many times I heard her sing the national anthem. Her title provided her with a platform to advocate for issues that were important to her and people listened. I wanted the same.

During my reign I’ve partnered with Dress for Success Charlotte, an organization that is important to me. I’ve done some fundraising, clothing drives, and other events with DFSC and I love being able to bring more attention to the organization because of my current title.

Q: What do you hope to accomplish as Miss North Carolina USA?

A: In addition to raising awareness about Dress for Success Charlotte, I also enjoy talking about fashion in the workplace and my blog, White Collar Glam. As women strive to gain equal footing in the workplace — especially in law firms — it is important to ensure that we are adequately prepared for the office. That means know­ing what to wear almost as much as it means knowing the substan­tive part of our jobs. I built my blog to make sure women have the resources and information we need to be well dressed at work. Dress for Success Charlotte does the same for women who can’t afford clothing on their own.

Q: What is it about fashion blogging that keeps you en­thralled?

A: When you look good, you feel good, and you perform well. That’s not to say that putting on a nice suit for work, by itself, is going to turn you into a great attorney, but there’s something to be said for the effect your clothing has on your self-image, the effect it has how others perceive you, and the quality of work you produce because of it. Blogging about fashion in the workplace is impor­tant to me because I want women to be armed for the workplace in clothing that will put us in the best possible position to achieve success.

Q: How do you set priorities and balance all of this?

A: I had to be realistic about each of my commitments and the time they take. I used to think my blog didn’t take much time to maintain and that my role as Miss North Carolina USA would only require a few appearances each week. When I took a hard look at the number of hours I spent each week on my blog and my title, I realized there just weren’t enough hours in a day to devote to each of them. I had to restructure my blog and figure out how I could continue to be Miss North Carolina USA while maintaining a full-time practice at work.

Perhaps most importantly, my firm has been incredibly supportive of me and my pursuits. They supported me doing Leadership Char­lotte (I’m currently in Class 40), there are a number of attorneys and staff from my firm who follow my blog and read my articles, and I can’t tell you how many people donated to Dress for Success Charlotte when I organized a clothing drive at the firm. I’ll be com­peting at Miss USA this summer and I’m glad to have the encour­agement and support of my colleagues while I prepare.

Q: Was there a person or event in your life that inspired you to be an attorney?

A: I have five siblings and I’ve always been the one to negotiate with our parents when we got into trouble or wanted something changed. I can’t say there was a single event that made me think, yes, this is the career for me. Instead, it was an eventual realization that I enjoyed advocating for others and took pride in the fact that people could and would trust me to represent them in matters small and large.

When I graduated from high school and started school at the Uni­versity of South Carolina my stepdad, David Simpkins, (who is also a lawyer and, like me, is licensed in both North Carolina and South Carolina) helped me find a local law firm I could work for while in undergrad. He has been a constant help and source of inspiration for me.

Q: How has your membership in the North Carolina Bar As­sociation helped you as an attorney?

A: It has propelled my career forward. I was introduced to my cur­rent firm through a the Minorities in the Profession program of­fered by the North Carolina Bar Association. I wouldn’t be where I am without the people I’ve met and the support I’ve received from NCBA.

Q: Tell us about your law practice.

A: I concentrate my practice in complex civil litigation. I represent clients in land-use and property related cases, construction dis­putes, and business litigation. One of my favorite clients is a good friend of mine — Nia Franklin, the reigning Miss America. She’s from North Carolina and we were introduced through pageantry when she competed in her first preliminary competition in 2015.