Written by Davidson College student, Clara Hudson ’28
Who knew shoes could be a canvas? For Jacary Lightsey ’27, it started with a love for art and drawing in his free time.
He was limited to drawing on paper until his sister planted the idea of drawing on shoes into his head. It started with painting Tweety Bird on a pair of shoes for his sister’s birthday, and now, many years later, Jacary has just painted shoes for radio personality Sway Callaway. Jacary’s passion for art and motivation to chase his dreams are the foundation of his shoe customization business, CaryMadeThose.
Jacary truly does it all. He is a D1 student-athlete on Davidson’s football team, majoring in Film, Media, and Digital Studies, a campus leader, a Resident Advisor, and an entrepreneur. If there is a place where someone can juggle being a full-time student, football player, and artist, it’s Davidson College. CaryMadeThose began with an artistic background and an appreciation for shoes, and thanks to support from the Hurt Hub@Davidson and the Try It Fund, it was able to continue moving forward.
CaryMadeThose is built on identity as an art form. Jacary captures identity on a pair of shoes because he believes your shoes reveal more about you than words ever could. His motto is that “your feet are the first thing to hit the ground” and should tell your story before you even speak. He reflects that his business is the “missing outlet in people’s lives,” as you certainly can not find shoes that express your identity at the mall. CaryMadeThose fills a gap in the fashion world by allowing customers to wear their vision on their feet.
Jacary’s shoe customization process begins with an idea, goes through the design process with acrylic paint and stencils, and then finishes with an ecstatic customer. His art skills are unquestionably impressive, but he needed a helping hand to continue running a successful business and show the world his shoes. The Try It Fund gave Jacary the opportunity to hit the ground running and accelerate his business. He used this funding to buy more materials and invest in marketing. After receiving the Try It Fund, he was inspired to apply for the Avinger Impact Fund and is a spring 2026 winner. He’s made many successful sales (including a pair of shoes for Doug Hicks, pictured above) and recently went on the Davidson Entrepreneurship Club San Francisco trek over spring break. He reflected that this trip gave him many insights into building a brand and taught him the value of learning from different industries and how they approach growth and innovation.
Jacary and his business are continuing to grow, and he is excited to keep learning. Through mentorship, funding, and valuable connections, CaryMadeThose found its way out of his dorm room and is making its way onto the feet of many. Looking forward, Jacary hopes that his drawings can make their way onto other clothing items and be known as a brand that tells your unique story.
If someone has an idea but is afraid to go for it, take it from Jacary, and don’t be scared to take risks. His number one advice to others is to utilize your passions and keep going. He doesn’t just want to sell shoes; he wants to build relationships and let others know that they are part of something when they wear his products. Jacary’s talent and creativity have given many the opportunity to let their shoes tell their story.
The Try It Fund has been made possible through generous support from the Charlie Hinnant ’72 Fund, Davidson alums, and other community sponsors. Applications open the first day of each semester and close at 10pm EST the last day of fall or spring break, depending on the semester.
