The Billykirk Schoolboy Satchel ($355) wins our vote for its timeless looks and size. Made from 100% vegetable tanned leather and measuring a shoulder-friendly 14″ L x 10″ H x 4″ width, it’s the perfect bag for hauling your tablet or ultralight laptop around town without being mistaken for a bike messenger. Removing the shoulder strap also lets the satchel pass for a rather sharp briefcase. It’s available in both black and rich brown.

Buy Now: $355