Founded in 1967 by Gwendolyn and Norris Ward, Gwynn's began as a modest 600 sq ft store specializing in women's clothing brands like Bobbie Brooks and Villager. By 1970, the store had moved to a nearby shopping center, expanding to include children's clothing, gifts, and menswear. 

In 1977, Gwynn's relocated to a larger space and continued to thrive under the leadership of Marshall and Lynn Simon, the founders' daughter and son-in-law, who purchased the store in 1990. They further expanded Gwynn's by building a 22,000 sq ft storefront in Mount Pleasant, South Carolina in 1992.

Significant renovations in 2016 introduced luxury private shopping suites and an expanded tailoring shop. Celebrating its 50th anniversary in 2017, Gwynn's achieved record sales for nine consecutive years by 2019.