Tom Bihn's Empire Builder briefcase — $190
As Jason O'Grady suggests in his, "a computer bag is the ultimate technology accessory because it has to be functional (protective) and has to look good at the same time." I prefer a simple case that looks more like a briefcase and yet still can offer plenty of room for a laptop, iPad, accessories, and even books.
My bag of choice is the Tom Bihn Empire Builder briefcase, which can hold an amazing amount of gear. I've used it every day for years now, pack it really full with heavy items, and still, it looks sharp.
The Empire Builder has a very large main compartment, which is easily accessed from the top through a zipper. There's a long side pocket under a flap as well as a compartment with various organizational pockets. On the side are a set of zippered pockets for easy access to papers, books, phone and other items. There are key straps and all kinds of niceties.
What is so convenient about this bag is that it's engineered to stay upright — it doesn't want to fall over! The front, back, bottom, and sides of the Empire Builder are padded and stiffened by foam, which offer a basic level of protection and to maintain its structure. If I'm going a short way to a meeting by car, I just slide the computer in the main compartment. Otherwise, I use the Brain Cell protective sleeve the company sells.