If you commute through rain or shine, you might want to invest in a truly waterproof messenger bag like the Pacific Outdoor Equipment Vancouver Bag. Welded zippers and waterproof fabric keep out moisture even in a serious downpour. Aside from keeping your items completely dry, the Vancouver sling bag keeps them organized. The interior houses three vertical pockets and a zippered mesh pouch, and the main compartment is big enough for a jacket, a change of clothes, and a bag lunch. The flap features a zippered pocket with a full organizer for you pens, cards, cell-phone, and other digi-widgets.