Here’s a look at the busy day of Cheslie Kryst, Charlotte attorney and Miss USA 2019
It’s pitch black outside at 5:05 a.m. on a Friday morning and Cheslie Kryst rushes into the Dowd YMCA, hair in a high bun, a long-sleeved Gamecocks T-shirt on, just in time for the 5:10 a.m. spin class.
She hops onto her usual bike, second row, center, starts her warmup, and when she hops off 40 minutes later, she’s barely dewy. “It takes a lot to make me sweat,” she says.
She’s a regular in this class these days, and for good reason. She’s Miss North Carolina USA, and in less than a month, the 27-year-old will walk across a stage in only a swimsuit and heels, in front of millions of TV viewers for the Miss USA pageant.
Her daily schedule is enough to make most people sweat. Today, she must:
- Return to her apartment after the gym, do an abs workout, dash off a few thank-you cards to groups who have invited her to speak, eat breakfast, and spend an hour on her hair and makeup. (More on the hair and makeup later.)
- Arrive at her desk in the uptown Poyner Spruill law firm by 9 a.m. to draft a contract for client Miss America Nia Franklin, and negotiate a personal injury case for another client.
- Zip to the tailor’s during her lunch break to get a few dresses pageant-ready.
- Work through the afternoon, then change into a pale-blue confection of an evening gown in her office restroom.
- Pull on her crown and sash in the car on the way to emcee an event at the Mint Museum uptown for Autism Charlotte. (While driving, she’ll practice giving 30-second answers to a list of 200 questions she created to prepare for the Q&A portion of Miss USA.)
Cheslie Kryst is a pageant queen. And a civil litigation attorney. And a popular fashion blogger. (More on this later, too.)
She knows that much of the world sees pageant girls as only pretty faces, and, on a larger scale, unfairly judges women based on appearances — especially in the workplace.
She’s hustling hard to change all that.
Beauty’s double-edged sword
Kryst is one of those women who can’t help but turn heads when she walks in a room. She’s tall, with supermodel features, perfect skin and a statuesque build.
Ordering a Chipotle lunch while en route to the tailor’s shop, seven hours after that 5 a.m. spin class, both men and women steal glances as she stands in line in a pink floral blouse, pencil skirt and trim camel coat.
Most work days, Kryst is careful to tone down her look, keeping makeup to a minimum and pulling her naturally curly, extremely voluminous hair into a neat, high bun. (When she wears it down, strangers have been known to touch her hair and ask if it’s a wig, prompting her to flip her head over to prove it’s all hers.)
But today, with the Autism Charlotte benefit on the schedule, she’s got her hair down and natural. It took about an hour this morning, and that was the get-ready-quick version. (To do her hair the right way, she says, would take upwards of three hours to finger-curl each and every lock. Today, she only focused on the curls in the sections of hair surrounding her face.)
For all the emphasis our society places on beauty, Kryst knows the double-edged sword that is being young and striking. It opens doors and, in her case, wins contests, but also has the power to distract — or cause her to be dismissed.
Courthouse security guards will require her to show her bar card to prove she’s an attorney so she can access her laptop and cell phone during proceedings; something older — especially older white attorneys — don’t get asked, she says.
The same goes for fellow law professionals meeting her for the first time. “Rather than asking me about whether I’m going to argue this or that, I get asked, ‘Are you the attorney?’ “ she says.
At a law school moot court competition one day in 2017, she and her female partner faced off against two male students, and afterward, one of the judges — a fellow black woman — had only one piece of advice after Kryst’s 20-minute oral argument: Wear a skirt next time. (She had worn a pantsuit.) Kryst posted about the experience on a Facebook page called Pantsuit Nation.
The post got 28,000 likes and 1,900 comments, and it fueled her desire to launch a fashion blog, White Collar Glam, dedicated to helping career women dress professionally. The blog posts, with photography by one of her younger brothers, range from frank advice and how-tos (“Is the double-breasted blazer for you?” and “Never wear these 10 items to work”) to posts about her favorite outfits and where to buy them. Visitors number in the thousands per month.
’Power behind pageants’
For as much as Kryst loves dressing up, she wasn’t raised a pageant tyke like the ones we see on reality shows like “Toddlers & Tiaras.” But she did grow up seeing the pageant world from the inside — thanks to a mom who participated in pageants.
Her mom, April Simpkins, was listening to the radio one day in 1997 when she heard an ad for the Ms. Petite North Carolina contest, geared toward women 5-foot-5 and shorter.
Simpkins had always been physically fit, was comfortable speaking in front of crowds, and was a classically trained pianist and singer, so she entered the competition. And despite the fact that she “did everything wrong,” she laughs, (such as the novice move of wearing a watch during the swimsuit competition) — she won.
In 2002, Simpkins dipped back into the pageant world, becoming Mrs. North Carolina US in the Mrs. America US pageant system. She used the title to publicize her platform, encouraging parents to volunteer in their children’s schools. Although it was a juggle balancing family life (she had four kids at the time and would go on to have two more) and running her own human resources company, she made being a pageant queen look intriguing to her two girls.
“I remember seeing people paying attention to every word my mom said,” Kryst says.
Simpkins says it was during her term as Mrs. North Carolina that that young Cheslie, who preferred pulling her hair back and reading books to dressing up and playing with makeup, “realized there’s some power behind pageants.”
In ninth grade, Kryst entered and won her first pageant — Miss Freshman at Rock Hill’s Northwestern High School — and when the family moved and she transferred to Fort Mill High School, she won the Miss Fort Mill High School pageant.
As Fort Mill High’s pageant queen, “she blossomed,” her mom says.
“Her focus was not on just wearing a crown and a sash,” Simpkins says. “I knew then that she was going to compete for the right reasons. She didn’t need praise and accolades.”
Determined to win
Kryst took some years off pageants while earning her bachelor’s degree at the University of South Carolina, but got back in the game during law school at Wake Forest University.
She tried a total of four times to win the titles of Miss North Carolina and Miss North Carolina USA (twice in the Miss America system, twice in the Miss USA/Miss Universe system), and although she was in the top 10 all four times, she didn’t bring home the crown until last November, when she won Miss North Carolina USA.
The local pageant world is small, so it’s no surprise that she’s friends with the current reigning Miss America, Winston Salem-native Nia Franklin. The two met in 2015 when Franklin attended an interest meeting for the Miss Metrolina pageant — a title Kryst held at the time.
“I thought, ‘Who is this beautiful woman? I can see her abs through her dress!’ ” Franklin recalls.
Franklin, an opera singer and composer, didn’t win the Miss Metrolina crown that year, but she won the pageant’s talent competition for her opera singing. Kryst sent her a Snapchat that night with encouraging words: “You need to compete again!”
Franklin tried for Miss Thomasville, and again was denied the crown. Kryst was in the audience.
“I remember going into the bathroom and sobbing and Cheslie came and found me and said, ‘Pull it together. You need to snap out of it.’ “ Franklin says.
And she did. Franklin moved to New York City in 2017 to start a Kenan fellowship at Lincoln Center, and decided to go for Miss New York in the Miss America pageant system. She won, and then went on to win Miss America last September.
The day after her victory, faced with stacks of contracts to sign, she called Kryst and asked her to be her attorney.
“She just is a force. The confidence and the poise she exudes,” Franklin says. “She’s a very smart, intelligent woman, and why wouldn’t you want a friend or lawyer like that?”
’How hard can it be?’
Franklin says she’s enjoying her year as Miss America. The day she talked for this article she was prepping to serve as host for four shows with the New York Philharmonic. But these are tough times in America’s pageant world.
The Miss America organization has been beset by internal drama and both Miss America and Miss USA have been suffering from declining ratings for years. Last year, just 4.3 million viewers tuned in to the Miss America competition (half the number that tuned in five years earlier), and only 2.4 million tuned into Miss USA, according to the Hollywood Reporter.
The Miss Universe/Miss USA system grabbed headlines in 2015 when then pageant co-owner Donald Trump was forced to sell his portion of the Miss Universe organization after offensive comments he made about Mexican immigrants drove away NBC and Univision. Then there were reports that Trump entered the Miss Teen USA dressing room .
Kryst acknowledges the drama. But there are too many plus sides in her mind to turn away from pageants.
She’s become a master at public speaking and emceeing. She forms alliances with community groups. Last month, she emceed a breakfast fundraiser for Big Brothers Big Sisters of Central Carolinas, and the next week was voted onto the local organization’s board.
“Before I won, I thought, ‘How hard can it be? You show up to an event and then go home. It’s an hour of your time,’” she recalls. But for most events, especially galas where ballgowns are required, there are remarks to prepare, organizers to coordinate with, outfits to procure (and in some cases, return to sponsors who lend them out), and thank-you notes to write afterward.
Franklin cuts right to the chase: “We are very well-spoken women, and it’s because of these titles. I’m hosting the New York Philharmonic this week. I’m not going to be standing there just looking pretty. I’m going to be speaking.”
What if she wins? What if she loses?
For Kryst, life after the Miss USA pageant on May 2 is a big question mark.
She’s already told her apartment’s leasing manager that she’ll be moving out by June. If she wins Miss USA, she’ll put her law career on hold, sell her car, move to New York City, and live largely out of a suitcase for the next year.
If she loses, she’ll put an offer in on a Charlotte house she’s already picked out, continue her work at the law firm, and dive deeper into her blog and community roles. Because of her age, she’d no longer be eligible to compete in the nation’s two biggest pageants, Miss America and Miss USA, but there are others she could qualify for. (Kryst says she doesn’t plan on entering more pageants, but “I never say never.”)
While she’s doing everything in her power to secure a Miss USA victory, but she believes her odds are small.
“You could have your best night, and (a judge) could just like somebody else better. Somebody could just not like your hair or think your dress sucks,” she says.
On this Friday night, 15 hours after her YMCA workout, cameras flash as she co-emcees the Autism Charlotte benefit alongside a 19-year-old with autism. She seems to float in her Cinderella-like gown, drawing cheers at just the right moments, and swooshing through the crowd displaying diamond earrings that are up for auction.
In a couple of hours, this event will be over and Kryst’s marathon day will end. She’ll get into her car, put her tiara and sash in their case, and maybe rehearse a few 30-second interview questions on her short drive home.
For Cheslie Kryst, these days, there’s not a moment to waste.