One of my favorite tote companies is Sea Bags, which is a Maine-based designer and manufacturer of items made from recycled sails. Their bags are incredibly sturdy and preppy. I proudly carry mine in Denver as a reminder of the East Coast! Sea Bags is currently collaborating with Woolrich, which has the oldest continually operating woolen mill in the United States. The plaids are beautiful (my favorite is the predominantly red and gold plaid called "Harvest"). The iPad cases and travel kits would even be a great gift for the impossible-to-shop-for male.
All images credit to Sea Bags.