It's somewhat hard to find a classically styled bag that can be used every day for years to come. Paul Smith's Antique Leather Despatch Bag ($575) might be a little on the expensive side, but break down the price per day of use, and you'll see it's starting to look more and more like a great deal. Inspired by vintage mailbags, the versatile bag has a perfectly aged leather exterior, suede lining, and an adjustable canvas strap with antique brass buckles.