In 1892, Milwaukeeans hailed the Matthews Brothers Building as a pivotal structure in the development of the downtown commercial district. The Matthews Brothers Company was a custom manufacturer of high-end interior woodwork and cabinetry. Its somber brown brick and terra-cotta exterior fit the 1880s taste for dark-colored buildings, which changed a decade later when the City Beautiful movement popularized the construction of numerous gleaming white buildings along W. Wisconsin Avenue. The Grand Avenue Mall’s third-floor deck provides good views of the building’s upper levels with its terra-cotta decoration. Notable details include lion’s heads in the sixth-floor cornice, richly ornamented spandrels, and a large terra-cotta cartouche bearing the Matthews Brothers’ monogram at the northeast corner.

From 1912 through 1994, the ground floor housed a Woolworth’s store, leading to its popular identity as the Woolworth’s Building. The street-level storefront was restored during the early 1980s when the structure became part of the three-block-long Grand Avenue Shopping Mall.