The specified phrase appears to be a nonsensical combination of disparate concepts: a type of clothing, a governmental directive, and a former U.S. president. It is highly unlikely that these terms are connected in any meaningful or official capacity. The combination lacks any discernible real-world basis.
Given the lack of a verifiable connection between these elements, it is impossible to discuss any importance, benefits, or historical context. Executive orders pertain to directives issued by the executive branch of a government, typically concerning the administration of existing laws. Clothing styles are matters of fashion and consumer choice. There is no apparent reason to link these domains.