I bought a medium size classic messenger in 2000 and only replaced it in January 2011. After nearly 11 years, it was still waterproof, comfortable, and professional-looking with very little fading or visible wear despite the fact that I took it EVERYWHERE (including 3 years in Africa). I can honestly say it's the highest quality bag I have ever owned.

Pros: It is the perfect size for a laptop, or for a change of clothes and a lunch, or for books and other things needed in high school/college/grad school. The adjustable strap makes it comfortable (and easily adjustable) for any size person or any size item you need to put in the bag. It looks professional but still a little "edgy" and stylish.

Cons: Not having a grab strap is a little irritating (but as another reviewer said, on the website you can order one with a grab strap). It also takes a little while to break in so that it fits well on your body, but I think a couple of weeks with a stiff bag is well worth it!

I would DEFINITELY recommend this to a friend!