In the early 50's, Reyn McCullough, a visionary merchant who owned and operated a successful men's wear store on California's Catalina Island, saw the growth potential the Hawaiian Islands had to offer. Statehood was imminent — so was the introduction of jet travel — and Honolulu was soon to be a short jet ride from the West Coast. So Reyn packed his family and moved to Hawaii. Within a few years, the growth of Reyn's Ala Moana and other new Hawaii locations convinced him to sell his Catalina business and concentrate his focus in the Mid-Pacific.

Enter Ruth Spooner who, in 1956 had established Spooners of Waikiki, and, with her one sewing machine operation on Waikiki Beach, was cultivating a reputation for the best 'kine' custom surf trunks in the islands. She made swimwear and shirts that Reyn designed, eventually selling him her business in 1962. Reyn set up four sewing machines in the basement of his Ala Moana store, and merging the two company names — Reyn Spooner® was born.