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A saddle shoe is essentially a whole cut shoe with a saddle reinforcement across the main stress area. It was developed for gym and fitness class in the US in the early 1950’s. In the post-war era of jive and Elvis Presley, the two-toned shoe replaced the penny loafer. Some may think the shoe is a summer or spring shoe, but I feel it can be worn year round. Your Life Choices Creates your Lifestyle.