A canine saddlebag and rain gear assembly for stowing items and deploying rain gear includes a first panel that is configured to position over front shoulders of a dog and to couple to front legs of the dog. A plurality of second panels is coupled to the first panel and defines a plurality of pockets. A third panel is reversibly couplable to a front edge of the first panel. A hole is positioned in the third panel and is configured to insert a head of the dog such that the third panel is positioned over a chest of the dog. A sleeve is coupled to the third panel proximate to the hole. A hat is positioned in the sleeve and is reversibly extendable from the sleeve. The hat is configured to cover the head of the dog. The pockets are configured to stow items.