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Origin of Jockeys Skull Caps The skull caps worn by jockeys came to this country from Australia by way of Vancouver, British Columbia. The late Robert Leighton, a noted Vancouver racing authority, was visiting the land down under in the early 1920s when he noticed the riders were wearing a sort of wicker-basket headgear. Leighton brought the skull cap back with him and introduced it in Vancouver, and now it has become standard equipment wherever horse racing is held on this continent.