Originally trademarked in 1932 as Crosby Square Authentic Fashions and known affectionately as The House of Crosby Square, the brand is widely considered by both historians and vintage enthusiasts alike as epitomizing the iconic and high quality American men's footwear fashionable in the first half of the 20th century. Early examples of Crosby Squares are coveted by collectors for their superior construction and (at the time) cutting edge styling. During Crosby Square's golden age, spanning from the early 1930's to the mid 1960's, the brand was quite literally a household name and heavily advertised in the major publications of the day such as Esquire, Life, The Saturday Evening Post, Time, and Playboy.

In point of fact, Crosby Square actually traces its shoemaking lineage back to 1867, when partners Alexis Beals and Ezra Torrey, originally from Boston, moved to Milwaukee, Wisconsin and began producing shoes under the name Beals, Torrey & Co. Beals and Torrey flourished during WWI due in large part to government contracts for boots as the country mobilized for the Great War. In 1925, after the passing of the original founders, the business was acquired by a Milwaukee shoe industry veteran, Walter J. Booth. Booth, previously the vice president and sales manager for another prominent local shoe firm, shrewdly decided to focus his newly acquired company's efforts on its premium men's welted shoes and shuttered his less profitable women's and children's shoe divisions. At the time, most well heeled American men looked across the pond to Savile Row for their fashion cues. British brogues and oxfords were the preferred choice for the elite few who could afford to journey to London and have their shoes custom made. Booth decided he needed a new brand name to evoke the romance and sophistication of the popular British styles. After much deliberation, he settled on the name Crosby Square, inspired by the area in London renowned for its bespoke shoe craftsmen. The name stuck and the brand grew and expanded, particularly in the boom years following the Second World War. Even President Harry Truman himself, famous for always being smartly dressed, was a fan and the company would proudly produce his custom made oxfords in size 8.5 C.