This disclosure relates to a messenger bag system having two bags and a collapsed and an expanded configuration. The two bags are connected by one or more connecting members. The bag system is configured such that the connecting member(s) can drape over a seat of a chair when the system is in the expanded configuration. Each bag has one or more retaining members. The retaining member(s) of one bag are configured to be adjacent to a retaining member of the other bag when the bags are in the collapsed configuration. A securing member is used to secure adjacent retaining members to keep the bag system in the collapsed configuration.