With the Great Depression beginning in 1929 and lasting throughout the 1930s, Okolona was hard hit. The U.S. Census figures indicate a 47% loss in population from 1920 to 1940. All three banks closed and none existed at all for several months. In 1934, the Mobile and Ohio Railroad provided the only major payroll in Okolona. The only substantial new construction during the 1930s was the U.S. Post Office, built in 1937, with Public Works Administration funding.

"Soon after World War II, Okolona experienced a short period of growth. Beginning in the 60's through the 90's, furniture manufacturing was an enormous part of the economy of Okolona. There were some twenty-five plus factories making furniture. During the late 1990's to the present, furniture manufacturing has declined. Presently, there are 12 factories with approximately 1550 employees.

During the past two years, national and regional retail stores, restaurants, gift shops, boutiques, and a resurgence of furniture manufacturing have dotted the landscape. Okolona's estimated retail market has increased to approximately 15,000 persons although the population within the city limits of Okolona has declined over the past decade.