As I understand it, "Brown shoes" mostly referred to Army (USAAF) officers who converted to the Air Force in 1949. The USAF had a new dress/working uniform of a blue suit and white or light blue shirt and black shoes. If the officer started out in the USAAF, they were grandfathered and could either wear the new uniform or the older Army khakis and brown shoes.
By the 1960's, "brown shoes" were senior USAF officers who had been around long enough that they had earned their commission in the Army, during or just after WWII.
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