How Harold Cotton turned a struggling hat shop into a booming business in the 50s

At the age of 15, Harold Cotton barely made ends meet shining shoes for a living. As much as this trade raked in a little, it meant a lot to him, because that was what led him to his door of greatness when he went looking for his cousin at Bob’s Hat Shop one fateful day. When he asked Robert Taylor, the owner of the shop, for a job with modest expectations, Robert asked him to shine his shoes to test his ability to deliver on the job. His display of exceptional skill, using rag and brush, impressed Robert, who offered him a job that same night.

Bob’s Hat Shop, which was a wholly owned black business, was into the cleaning and repairing of hats, as well as shoe shining. The business was allowed to operate based on a certain degree of flexible segregation, where both blacks and whites enjoyed their service in different segments of the shop.

The 1930s weren’t favorable times for African-American-owned businesses, therefore, Harold shined shoes part-time at Bob’s Hat Shop and engaged in other menial jobs at the cigar factory and the corn mills. Despite earning a diploma from the North Carolina Agricultural and Technical College, Harold had to still work tedious jobs, including driving delivery trucks and working at the hat shop, according to American history.

When Mr. Taylor passed away in 1948, Harold decided to migrate to the North in search of better opportunities and to pursue his dreams. One of those dreams included opening his own store in Chicago. To attain this, he went to the Chicago School of Shoe Rebuilding in 1950 to enhance his skill in hat cleaning and repair.

Before he could live his Chicago dream, he had a call imploring him to take over Bob’s Hat shop because the man who bought it was gravely ill. In 1953, Harold began the business of cleaning and repairing hats at the place where he birthed his dream.

The 1950s presented a boom in business for Harold, who grew a huge customer base. However, business took a nose dive after a shift in fashion taste. Many believe it might have been sparked by President John F. Kennedy who attended his inaugural address bareheaded, since then, many began to dress without hats. Many hat businesses declined, but Bob’s Hat Shop left its legacy in downtown Greensboro.

In the heat of the civil rights movement and sit-in protests in 1960, Harold decided to desegregate his store. Irrespective of the race of his customers, they were allowed to sit at the front and have their shoes polished. This was considered one of the bold courageous steps taken to challenge the Jim Crow laws.