This is my second messenger bag and my first from Timbuk2. My first was a Chrome, which is far superior to this. If you have the money for a Chrome, get it. But I didn't have the money for one, so I got this. If it wasn't drastically on sale, and I didn't have a gift card, I would have been sorely disappointed. First because of the unwieldy quick adjustment buckle. It digs into my ribs constantly -- to the point that I took it off, and reduced the functionality of the bag. But more importantly, this bag does not adequately protect my books and electronics from the rain. I got it just to carry around my laptop and books for school. But the bag's flap does not completely cover the main compartment. As a result, water gets into the bag and my books are wet. I am disappoint.
In addition, this bag does not come with a waist strap, as most other serious messenger bags do. The waist strap keeps most bags from sliding around in heavy cycling.
Otherwise, it's a good bag. Nice for walking quickly from the bus or car to class, but not really for cycling in the rain.