Over the past 40 years I have had all kinds of briefcases and they did the job as expected. My most recent job requires that I bring my own uniforms to work. I thought the messenger bag would give me the room I need for work and a convenient carry-on bag for 2 or 3 day trips. I satisfies my needs and I like the fact that is different, it's neither a briefcase nor a backpack.
I received this bag as a present complete with monogram. I had been carrying a very nice leather briefcase for several years so my initial reaction was while much appreciated I was perfectly happy with what I had. But, it being a present, I thought I should at least give it a try and, wow, I fell in love. This bag is roomy and comfortable to carry. What maxed out my leather bag hardly made a dent in this leaving lots of room if I needed it. It is also extremely well built and takes lots of abuse. I've been carrying it for well over a year and couldn't be happier. Recently the zipper pull to the main compartment come quite unexpectedly off - very surprising for something so well made. LL Bean is replacing it complete with monogram. Both the bag and LL Bean are tops and highly recommended.
This bag replaces an older similiar style LL Bean canvas bag I had for 10 years. I loved my previous bag but the strap kept coming loose every day and it was time for a new. I do like features that the old bag had - like the short carry handle on the top in addition to the long over the shoulder. This is due to the way I would take it out of the car prior to throwing it over the shoulder. The new strap won't come loose because it has a belt closure. The side pockets velcro is super strong as other reviewer mentioned, you need two hands to undo it. The bag is the same great quality and looks very nice with the leather trim. I have the british khaki. If you think your bag will get into dirt, I suggest a darker color. The monagram is nicely sized right in the center front. I fit my lunch, mini purse, shoes, sunglasses, water bottle, and more. Plenty of room.
Most days I have to carry my 13" laptop, two to three small/medium sized textbooks, and two to three folders, and it all fits perfectly inside the large pocket. The two outside pockets on either end are perfect for holding my umbrella, laptop charger, and a water bottle. In the zip pocket under the flap I'm also able to fit a planner and the smaller, regular sized books I have to read for some classes. I just got this in January, but so far it hasn't let me down! I got the olive color and it looks great!