The Monroe family's first involvement in shipowning was in 1897 when William Monroe bought the iron steamer Vindomora for shipping coal from South Wales. In 1912 his cousin, Kenneth Monroe, in association with two others, purchased the steamer Blairmore (later Ballater), and began buying coal direct from the collieries for export. Kenneth joined the army in the First World War and in 1917 the company's coasters were sold to J.C. Gould. In 1919 Kenneth set up the Monroe Shipping Co., Ltd., bought nine small coasters from J.S. Monks of Liverpool, and opened an office at 30 Brunswick Street, Liverpool. In 1920 he was joined by his two brothers, Robert and William. Ships were registered under various company names, and the name of Monroe Shipping was wound up in 1925. In 1931 Monroe Brothers Co., Ltd., was formed and became the predominant registered company. By 1936 Monroe Brothers Co., Ltd. transferred all the steamers under their management to Kyle Shipping Co., Ltd., and all new acquisitions had the prefix "Kyle" in their names.
Between 1939 and 1944 the three brothers died, and the business was run for the following two years by Mrs. Ann Monroe, assisted by her manager, Hector Oliphant. In 1946 her son, Kenneth, was demobilised from the Royal Navy and took over the reins, to be joined in 1954 by his brother, Robert. This began a change in the 1950s and 1960s to larger vessels and increased continental and transatlantic trade using motor ships. In 1969 the Kyle Shipping Co., Ltd.'s last vessel was sold to the Stephenson Clarke Group and in the same year the Monroe Brothers activated the St. Vincent Shipping Co., Ltd., and became minor shareholders and managers of two deep-sea ships. This company was eventually wound up in January 1979 but with the Monroes remaining as ship brokers, managers and shipowners' advisors based in Old Hall Street, Liverpool (see also James Chambers & Co., Ltd.). For further details see the attached catalogue.