Unlike your ballistic nylon work bag that looks roughed up and needs replacement every two years, a well-made Italian leather satchel like the Il Bisonte Unstructured Messenger A2067 will only get better-looking over time. Inside, a large zippered compartment fits most tablets (including the popular Nexus 7 and iPad mini), while dual pockets and a smartphone pouch handle your essentials. As you make the trek to the office every day, loosen the shoulder strap and hang it low during morning and evening rides; the bag will be working hard to develop wear patterns and a rich patina, enhancing your low-key look. [$878; ilbisontestores-us.com]