I'll start off by saying that I recently bought last years model of this same bag in medium. Once I saw this new bag with the different features I thought "Sure, lets try it out". However, I found that the medium bag I had before was massive! I had a ton of extra room in it after fitting in all my stuff. I decided on ordering the small this time and if I didn't like it, I would simply return it. But just to be safe, I ordered a medium as well. So here I sit with three different Timbuk2 bags. Here are my thoughts on the small and medium 2014 bags.
Small:
The small bag is great if you need to hold a laptop and a few folders. There are plenty of pockets to keep yourself organized and hold your smaller things. However, I found that this size was just not practical for me. I am a first year teacher that does not have a personal classroom meaning that I travel with my laptop, binder, lunch, water bottle, coffee mug, and several folders throughout the day.
With this bag, I was able to fit my binder, laptop, and the folders. It was a tight squeeze though and that bag looked stuffed with all of those things in it. Seeing as I still needed to fit my extras in it, this bag was sadly out of the picture.
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Medium:
Like last years bag, this thing is huge. I can fit all of my things mentioned in the small review with ease. Additionally, I can fit a mini first aid kit, mints, aspirin, post it notes, pens, pencils, and whatever other small things I need. The only problem that I found with this is that my water bottle (32 oz Nalgene) causes one side to bulge. Overall, it wasn't that big of a deal and I can learn to live with it.
When looking at the new features there were some things that I wish they didn't remove.
1) The new single pocket front. The three separate pockets on last years bag I found were more intuitive and had better organization.
2) The inner pockets. Unlike last year where there were several slash pockets, a velcro pocket, and pen spaces, this model has only slash pockets with one large zipper at the top.
3) Instead of the cam buckle, Timbuk2 included a small piece of fabric that you pull to tighten the bag. It feels a little awkward to use at the moment but it make just take some time to get used to.
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Comfort:
The new strap is amazing. The air pockets make carrying a heavy bag extremely easy and comfortable.
Again, this bag is great, you can carry a massive amount of stuff in the medium size with room to spare. If you're struggling between the sizes like I was, make sure you read the dimensions carefully. While the small can hold a 13" laptop easily, there isn't much room for anything else. The medium bag will give you plenty of more room to hold your belongings.
EDIT: Added some photos of the bags and their contents.
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