Where Are They Now? with Madison Simon

Where Are They Now? with Madison Simon

By: Kate Abraham

Madison Simon, a 2010 Ole Miss graduate, has made her mark as an alumna, holding a highly-sought-after retail buying and managing position while co-owning Gwynn’s in Mount Pleasant, South Carolina alongside her father. Gwynn’s is a luxury department store that attracts customers from all over the country and carries high-end brands such as Alice & Olivia, Gucci, Jimmy Choo, and Stuart Weitzman, among many others. Gwynn’s has also been seen on Southern Charm, a reality TV show on Bravo. Growing up in the middle of the family retail business, Simon has always had a keen interest in the industry. While at Ole Miss, she majored in Business, minored in Management, and had an emphasis in Marketing. Her passion for understanding the business of fashion, customers, and current trends has made her a well-versed buyer and successful manager. 

During her time at Ole Miss, Simon was attracted to the idea of the Grove and how fans, students, and alumni dressed up for football games. Oxford’s artistic and culinary aspects also won her over and played a part in her decision to attend the university. When asked what made her interested in retail, Simon recalls as a young girl watching her mom get dressed in the morning. She says, “when I would watch my mom get ready and pick out her outfits and put on her makeup and even down to the finishing touches of her lipstick, I would always fantasize that I would become part of that world one day.” 

Before settling permanently at Gwynn’s, Simon gained experience in the fashion industry in many different aspects. Her career kickstarted during her time at Ole Miss when she had the opportunity to intern in New York City for George Cortina, a stylist for Vogue and W magazines. Looking back on her time interning for Cortina, she shared a once-in-a-lifetime experience, “I went to Paris to assist a photoshoot for Vogue Japan where we shot with photographers Inez and Vinoodh and model, Daria Werbowy, and other amazing talents. It was so major and pretty life-changing for me.” Following graduation at Ole Miss, she made the move to New York City and landed her first job at Bergdorf Goodman. Alongside this experience, she also worked in the public relations and fragrance industries, further expanding her skillset. 

Gwynn’s has been a part of Simon’s life since before she was born. She grew up around the business as it is family-owned with her father, Marshall Simon, being the second-generation owner. Her experience working at the store officially began in high school with tasks such as handling phone calls, wrapping presents, and filing paperwork. Following her time living in New York City, she moved back home to Charleston, South Carolina. She began working at Gwynn’s and learning more about the family business with a wide range of responsibilities, including serving as a sales associate and attending buyers’ trips. She climbed the ladder and now holds the roles of women’s buyer, merchandising manager, and marketing manager. Alongside this accomplishment, she also established the in-house marketing and e-commerce department, which has proven to be a significant area of success for the store - with an Instagram that boasts close to 65,000 followers. 

Wearing many hats, Simon’s to-do list is continually changing. When asked what an average day looks like for her, she says, “honestly every day is different. Some days are spent more working on buying activities, some are geared more towards marketing, and some are more managing and putting out fires. It’s always interesting and never a dull moment!”  

Some favorites of Simon’s are attending New York Fashion Week, going on buying trips, coordinating photoshoots for the store with the marketing team, and developing relationships with different people. The list of tasks that Simon isn’t keen on is small, but one being budgeting. She says even though it isn’t her favorite, it is a very important part of the job. 

For many, a position such as Madison Simon’s at Gwynn’s is a dream. Her work ethic and accomplishments are an inspiration to many who desire to be in the fashion industry, and her example one to follow. To those with high aspirations, she says, “Don’t let other people influence your decisions. Be the person you want to be, and don’t waste your time worrying about what others think of you. You’ll get further faster is you stay focused and don’t worry about how you’re perceived by outsiders. It’s so basic but so important. If you want to sing, sing, if you want to dance, dance. Just be you!”

Photo Credit: Madison Simon