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Leo Espra’s career began with a passion for fashion that has opened doors to remarkable opportunities over the years. This July, one of those opportunities brought him to Orlando, where he served as a judge for the prestigious Miss Florida USA and Miss Florida Teen USA pageants.
The invitation was a significant milestone in his career and offered a new perspective on an event that celebrates confidence and personal achievement. Espra’s selection as a judge was made possible by the strong professional relationships he has formed in the entertainment and fashion industries, and he was honored to be invited by JaclynN. Stapp, State Director and Executive Producer of Miss Florida USA and Miss Florida Teen USA, to join the distinguished judging panel this summer.
“I’m grateful for her trust and for the opportunity to be part of such a respected organization,” Espra reflected. Although he has attended countless high-profile events throughout his career, Espra says serving on the judges’ panel in Orlando was unlike anything he had experienced before.
Instead of just observing a competition, he was entrusted with helping evaluate the contestants.
“It challenged me, inspired me, and gave me an even greater appreciation for the dedication these young women bring to the competitionại he said.
Known for his many talents, Espra works as a producer, luxury lifestyle curator, Vice President of Development & Creative Director for Good Entertainment, and Brand Ambassador for GreyVen.
His career has made him a familiar face in Los Angeles, where he has earned a reputation for his unique sense of style. “Fashion has always been an extension of my personality,” Espra shared. And with the pageant’s prestigious reputation in mind, he planned each look for the event to respect the occasion while remaining true to his signature style. His wardrobe featured custom-designed suits by Ton Chookhare, Creative Director of Chookhare & Sons, a luxury fashion brand with whom Espra has proudly collaborated for several years. The partnership was the perfect fit for such a high-profile event, as Espra said, “Ton has an incredible eye for timeless tailoring and understands my personal style, so each look felt authentic to me,” Espra said. “I personally styled the outfits and accessories to create a polished look that reflected both the prestige of the event and my own fashion aesthetic.”
While fashion had an important role throughout the weekend, Espra says the most rewarding part of serving as a judge was during the interview portion of the competition, when he and the other judges had the chance to engage in conversations with each contestant and learn about the women outside of their stage presence. Those interviews revealed each contestant’s ambitions, passions, community involvement, and personal values. For Espra, those moments reinforced that pageantry is also about character, intelligence, and philanthropy.
“The interview process gave us the opportunity to get to know each contestant beyond what the audience sees on stage,” he explained. “Hearing about their goals, their passions, and what motivates them made the experience incredibly meaningful.“Throughout the competition, Espra was dedicated to maintaining fairness and professionalism while evaluating every contestant. He found himself inspired by the confidence and personal growth demonstrated by the young women competing for the state titles. Watching them challenge themselves on stage and share their individual stories reminded him of the power of perseverance.
And as the event concluded, Espra reflected on the experience with gratitude.
“I’m grateful for the trust that was placed in me, the friendships I made, and the opportunity to be part of such a respected organizationạhe said.
Leaving Orlando, Espra carried home a new sense of inspiration and an even stronger commitment to his work in fashion, entertainment, philanthropy, and human connection. Serving as a judge for Miss Florida USA and Miss Florida Teen USA was an opportunity for him to witness the next generation of confident, driven young women pursuing their dreams. For Leo Espra, it was an experience that reaffirmed the value of leadership, integrity, and community while adding another memorable chapter to his career.
