When the Sartorialist posted this shot, dubbed "Bag Envy, West Village," we admired the subject's effortless style and instantly pegged him as a guy who knew the importance of buying quality items and then hanging onto them for life. Which is why (even with our fluctuating 401K balances) we're advocating this handsome bag by Jack Spade. It's big enough for a long weekend, but handy enough for everyday—should you have a lot to tote. Crafted from top-grain leather, it will last you a lifetime and only get better looking with age. Scott, this bag's for you. $625 at Blackbird, Seattle.