I have used my original Timbuk2 messenger bag for over 3 years, every day for school and work. When it came time to purchase a new one, I figured why not stick with something I'm used to? I opted for this new classic messenger bag. I am very glad I did. The material is just as strong, durable, and light as the original. It comes with an updated design and some new features. I really like the one handed strap lock. It is very easy to operate(make shorter when riding or longer when walking).
The only con I can think of is that the sizing is a little different from the original model of the bag. I purchased a medium since my other bag was a medium and it was somewhat larger than the original model. I guess I can't complain about the added storage space but it does make it a little bulkier while commuting on my bicycle or motorcycle. It also causes the stuff inside (laptop, books, etc) to shift. The bag does however have compression straps on the bottom to tighten down when you don't have enough stuff to fill it up. It is a hassle to always have to tighten it and loosen it depending on the amount you're carrying especially when you're in a hurry.
Overall a great messenger bag that I would buy again! 4/5 stars due to the sizing difference.
I'd also like to note that I purchased this bag since I wanted a new one and NOT because my old one was no longer functional. In fact my old one is still in great condition! This goes to show the durability of Timbuk2 products!