These bags fit within most US airlines' domestic carry-on size guidelines. Be sure to check your airline's specific policy!
Many airlines currently allow a primary carry-on bag (up to 22" x 14" x 9") plus an additional personal item, such as a briefcase. In this case, the best way to carry your driver's gear on the plane is with a helmet bag and a suit tote case. The helmet bag counts as your primary carry-on bag, and the suit tote case qualifies as a briefcase.
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The OMP City Bag is at home at the racetrack and in the boardroom. This messenger bag / laptop bag / briefcase carries your paperwork and other essentials.