Although there's a few leather messengers I really like, I generally prefer canvas messenger bags. To me they feel more comfortable and have a more natural look. Personally I usually go with more retro-looking than "high-fashion" bags, and just seem to find more of what I like in canvas bags. Some of the best canvas messengers around are made by Fossil. Their bags combine fashion together with superior quality. Stylish and durable, they're made using high-quality sewing as well as materials.
Some of my favorites include their Union City bag as well as the Wagner East-West messengers.

