During my 24 years in the Canadian Forces, we were strongly encouraged (okay, there was no real choice) to wear the poppy every year from the last Friday in October until November 11 as Bolt stated. The Canadian Forces follows the guidelines set out by the Royal Canadian Legion for the wearing of the poppy.
Speaking as a retired military member, I would say military personnel have no issues wearing the poppy before/during Halloween and that it in no way takes away from the respect for veterans and those who gave their lives in battle.
