This was the first New Albany location of retail giant F.W. Woolworth Company. Woolworth's arrived in New Albany around 1913, and located its ever-popular 5 & 10 Cent store in the south side of this building. By 1919, Woolworth's had expanded into the north half of the building, and was setting sales records for Indiana stores.

The first Woolworth's Cafeteria in the nation was started on the second floor of 220 Pearl around 1923, by Miss Mildred Sinex. In 1931, Woolworth's moved its store and cafeteria to the northwest corner of Pearl and Market streets. Karl Fenger Hardware, Steiden Grocery Store, and Winn-Dixie Supermarket all occupied the building for a period of time over the next 20 years. From the late 1950s through the early 1970s, the building became home to the popular Walter Kahn Department Store, home of the latest women's fashions.