I reviewed Timbuk2 messenger bags like crazy trying to find what would best fit me. I already owned the Freestyle and it was a bit too small to put all my work stuff in. The Freestyle is great for an iPad, Kindle, netbook, and has a good amount of room for more stuff for running around town. THIS Classic messenger bag is perfect! It can hold my 14" laptop. I did not buy it as a laptop bag, but I do carry my iPad in it all the time. It also holds my Kindle Fire as well. It holds "peechee" size folders for my paperwork and a bunch of other stuff! It has plenty of pockets to place things. I went to REI to compare my Small Classic messenger to the Medium one because my small one will not hold an insulated lunch bag. Only a paper bag lunch. The Medium Classic messenger was huge. It is twice as deep, but I do not need that much room. The Small is perfect and will fit under the airplane seat wonderfully. This Rev Red color is great for those folks who love the color red! I am very happy to have another Timbuk2 bag! These bags are durable and last!