It's a tough call. The backpack is enjoying a serious renaissance lately. And if your office is cool enough to get it, then it certainly makes a commute easy and transitions nicely into an off-duty bag as well. But you can't go wrong with a well-made leather messenger/brief either. We can't make that decision for you but we will say this: When it comes to a leather bag, you want it to be versatile, adaptable and most of all, durable. Of course, you want it to look good too. It's a piece you'll use everyday and thus, is worth investing some real money in.