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Dillard's is the outgrowth of a Nashville, Arkansas, department store founded in 1938 by William T. Dillard; its corporate headquarters remain located in the eastern edge of Little Rock's Riverdale area, and many of its executives and directors are members of the Dillard family.

Dillard sold the Nashville store to develop a larger one in Texarkana, Arkansas initially as the minority partner in Wooten & Dillard. In 1956, Dillard led an investment group that acquired the Mayer & Schmidt store in Tyler, Texas. This store eventually took on the name "Dillard's Mayer & Schmidt" until 1974, when it was replaced with a mall-based location south of downtown Tyler.

In 1960, Dillard acquired and turned around the failing Brown-Dunkin store in Tulsa, Oklahoma. The success of this turnaround was followed in late 1963 by acquiring the Joseph Pfeifer store in Little Rock, Arkansas, and in early 1964 acquiring the other main store in Little Rock, Gus Blass Co. Dillard used this as an opportunity to relocate his headquarters to Little Rock. In 1969, Dillard and his investors took Dillard Department Stores, Inc., public on the American Stock Exchange.

Thereafter, the chain grew rapidly as an anchor in suburban shopping malls, and took advantage of market conditions to acquire smaller chains as well as its ability to turn around locations that other companies could not operate profitably.