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on July 29, 2010
Pros:
Simple, compact design
Good organization pockets
Weatherproof lining
Quick access pocket
Sewn in shoulder strap for good stability
Small size is great for 13" MacBook Pro

Cons:
Velcro closure
No grab strap
No laptop sleeve

I was looking for a bag to haul my MacBook Pro 13" and work papers to and from my work. I wanted something compact, light, and comfortable and in a fairly conservative color. The small Timbuk2 Classic fit the bill. I really like this bag, although there are a few additional features I wish it had. I tried out this bag as well as the Timbuk2 D-lux, Timbuk2 Commuter, and Patagonia Half Mass in a local store before deciding on the small Timbuk2 classic.

===========PROS===========
1. Design. Simple bag. Weather proof lining. Organization pockets on inside for your iPod, phone, keys, pens, etc. Has a quick release extension to ease getting it on, but I don't find that I every need to use it with the small bag. adding it

2. Size. The small Timbuk2 is the perfect width for a MacBook Pro 13" and 8.5x11 inch papers without a lot of extra room on the sides for things to jostle around or get lost in the bottom. There isn't much extra room after putting in a laptop and few textbooks, but I found that the weight of the full small bag is about as much as I would want to carry in a messenger bag that puts most of the weight on one shoulder. The medium sized bag seemed to be a big step up in size and was too bulky for me. For days when I need more room, like for workout clothes, I just bring a second bag rather than carry around extra room with me every day. (If you have large bulky, but relatively light, items to carry around then you may want the medium or large bag.)

3. Neapolitan Pocket. So handy to have a pocket you can access without opening the bag. Enough said.

4. Divider. A pleasant surprise here. I was disappointed that the divider was not suitable for my laptop (see below) and had considered cutting the darn thing out of the bag. However, now I find myself using it all the time! It is a great for storing papers/reports so they are both protected and easily accessible. Sit down on the subway...pull out a report. Super!

5. The Shoulder Strap. The strap sewn in along both sides of the bag and is not removable. Having the sturdy wide strap sewn gives the bag a lot of stability. Bags with straps that clip on, swivel and pivot at the point of attachment. This bag doesn't wobble like that.

===========CONS===========
1. Velcro. The Timbuk2 bag has both clips and velcro for securing the flap. I hate the velcro. It is unnecessary because it already has clips, but worse it is noisy. I am reluctant to open the bag during a meeting because of the loud rIIIIpping sound it will create. There is no discrete way to open this bag. (Note: The velcro closure could be negated covering it with a velcro hook strip which I will do at some point.)

2. No grab strap. Other than the shoulder strap, there is no handle on the bag. I often find myself grabbing for a handle on the top of the bag which doesn't exist. You can get a grab handle if you build a custom Timbuk2 bag on their website, but you pay twice as much for the bag.

3. No laptop sleeve. Although the bag has a built-in divider which fits the MacBook Pro perfectly, only the inside side is padded (see my video). There is no padding on the outside or bottom of the divider. This means that if you set down your bag hard on the floor, you run the risk of damaging your laptop. I just use my existing neoprene sleeve with my laptop. It is too bulky to fit into the divider, but is quite secure in the main compartment of the bag. (Note: the D-Lux version does have a padded laptop sleeve. See my discussion on other bags below for why it didn't work for me)

===========Other bags I considered===========
Timbuk2 D-Lux: It has a padded laptop sleeve (although I wasn't impressed by the padding at the bottom of the sleeve), but it doesn't come in black which was a deal breaker for me. I also didn't like the modular organization system which attaches via velcro to the inside of the bag; the pockets weren't as securely attached to the bag which makes getting things in and out of the pockets more difficult.

Patagonia: What I really liked about this bag was that the padded laptop sleeve does not touch the bottom of the bag, the sleeve was a bit bulky and was oddly attached to the inside of the bag. Also the construction of the bag didn't feel as solid.

Timbuk2 Commuter: A bigger bag than the small Timbuk2 Classic, but with more functionality. It has a cool laptop case that flips out to be TSA compliant (i.e. you don't have to take the laptop out of the bag). It also has a grab handle (yeah!) and no velcro on the flap. It was 2nd on my list, but in the end I decided it was bigger than necessary for my daily commute. The laptop case is made to fit a 15" laptop although it my 13" didn't move around too much. I didn't like the detachable shoulder strap with swivel straps as much; I prefer the sewn in shoulder strap of the Timbuk2 Classic. However, this would be a great bag for airline travel as if gives a little more room than the Timbuk2 Classic and the TSA compliant laptop compartment. I may end up buying this as a second bag for traveling.

[...]
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on March 15, 2011
Bought the extra small size. Suspect it is the same details except the size of bag. **addendum: All the pockets are proportionate to the bag size. Just received medium. Pockets are more numerous and larger than XS. Much better for my big hands. Medium is big but not as big as expected. For my 6'2" it is ideal. Shop carefully as you increase size price does not increase proportionately when on sale.

Extra Small size fits my note book if I turn it sideways or put it in the main compartment. Basically this size is like a large purse meaning you do not have room for cloths. Hung it on the car seat backrest next to me. Handy to grab wallet, keys, pens, writing pad, water bottle, calculator, and other small things. When someone else gets in I swing the bag around facing rear seats. Well made in every way.

Liked XS enough to order a Medium size to carry cloths. If I wear shorts and T carry long pants and long sleeve plus wind breaker "in case" weather changes which happens often. These bags well suited to bike or bus travel. People with cars can carry TOO much with ease. Nice for travel or fairs too? When you have too much to leave it all at home take some with you, LOL.

Up to Medium there are good discounts. Large and above seem to stay closer to retail. Medium size is good for a few books and extra cloths. IHMO above medium good for more cloths and other LIGHT BULK. Large and above will cost more per unit space but medium will hold all the books, heavy stuff, carried comfortably. Add a laptop or notebook the weight will be serious weight on your shoulder. Medium makes most sense for price/couple books/warm or cold cloths change/AND lots of small stuff in many pockets.

Of course you will pick the size that you think is best consider this; XS is about 580cu", small is about 730cu"(+25%), medium is about 1590cu"(+220%). Note the last MEDIUM doubles space. It costs me maybe $5 more than small. Next size Large jumps much more (50%?). My cu" (cubic inch) estimates are off because the bags taper bottom to top. However the top flap allows lots of expansion up and out. My size estimates are just for comparison purposes based on listing. MEDIUM is more for the money, if it suits you, than any other unless you find a special deal which come and go fast and in colors you may not like.

Suggestion: prices seem to vary quite a bit from day to day or week to week. Pick you color and size and follow for a couple weeks. Saved me about 40%. It would help to SEE and Touch various sizes before selecting.
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on June 23, 2015
I SUPER LOVE LOVE LOVE MY NEW TIMBUK2 BAG!!!! It took me a very long time to decide on the size and color! I finally went with the red and it's absolutely awesome! The bag itself is huge! I wanted something big but this sucker is huge! I'll post a few pics so you can see what I'm talking about. And I'm not a small girl! I'm 5'7" and 140lbs give or take a few lbs! I got it to carry all my art supplies when going somewhere for the day. It's also great for everyday use bc I have a 3 year old who still requires quit a bit of stuff!
The feel of this bag is amazing I mean there's is no doubt this thing isn't gonna last forever! All the pockets are really well placed and I love the Neapolian pocket! I got the Medium but it's huge so I'm thinking I'm going to go ahead and order a small as well for everyday use!! Bc it's such an awesome bag!!!
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on February 5, 2014
The 2013 XS Classic Messenger is a straightforward bag with simple appointments: ballistic nylon exterior fabric, a divider (slash pocket), interior and under flap pockets, key tether, comfy 2" wide strap and quick adjust CAM buckle. There is no handle for a quick grab 'n go or cross strap for additional stability while biking or running. If you don't mind paying more for the latest and greatest, Timbuk2 Classic Messenger Bag 2014, a handle is now a standard feature, albeit the thinner strap is harder on the shoulder.

My main purpose for the XS Classic was to stuff it with an extra small Timbuk2 Snoop Camera Insert and use it to stow my EOS 6D camera. Although the XS Snoop insert is made for the XS Classic, fit is poor: the Classic is too small and the insert is scrunched and distorted, making it a PITA to pull cameras in and out. I also own a XS Timbuk2 Snoop Camera Messenger Bag, supposedly based on the Classic design, but it's deeper so the insert fits perfectly.

Sadly, I send the XS Classic back to Amazonland. I was tempted to keep it since it's so cute and well made, but it's too small for my messenger bag duties. I need the next size up. However, if your carry needs are modest--stow an iPad, windbreaker and water bottle--this just may be the perfect mini messenger.
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on June 3, 2014
Ok I have a few things to say about this product. I commute to work everyday by bike and I was looking for a smaller bag to substitute for my larger one during the summer where the weather is a lot warmer (read: I sweat a lot more). This bag had great reviews and came in a variety of sizes. So, onto the review..

PROS:
Very lightweight, plenty of pockets, size matches the description in the picture perfectly. Adjustable strap that you can change on the fly with the option to turn this into a backpack of sorts.

CONS:
I am not sure what "commuter" is able to use this bag unless they are smaller than 6'. I am 6'4" and I can barely fit any of my work clothes in here along with a lunch. This could be remedied, I suppose, by a larger bag, but I was looking for a bag about this size. I realize this is not the bags fault, but many of the reviewers say they use this bag to commute. So, my only guess is that they are the type who can bike far distances and not sweat so therefore wear their work clothes while biking. I unfortunately am not in that position. Now lets talk about the strap. It is adjustable so you can make it tighter on around your chest on the fly. That is great, except that the puffy thing they put on the strap to make it more comfortable only serves to let it slip and slide all along your back. When biking up hill (meaning im standing up on my bike pedals while pedaling), the bag will slowly move from your back to your side then to your front. This is a MAJOR problem as I do not want to keep adjusting the bag to my back every time I have to go up a hill.

Furthermore, when you tighten the strap, the way the bag is set up is the extra strap has no place to go. It just circles near the bag where the strap is sewn in and sticks out which can be very dangerous. I dont know if I am describing this well, but the only way to fix this would be to cut the excess strap once you figure out a length that works for you. I could not for the life of me figure out where to slide the extra strap so that it didnt create a huge loop on the side of the bag that could easily be snagged by something you were biking past.

CONCLUSION: this bag is great if: you are small enough that your clothes can fit in the bag. You do not commute long distances. You like to pretend you bike but you dont actually bike anywhere (its ok...i wore a lot of skater clothes and I never skateboarded). The bag itself is well made, no complaints there. This bag is not great if: you are a large mammal like myself. You do not wear your work clothes to bike because you sweat like a regular human being and thus would need to put your clothes in this bag. It leaves room for not much else. Basically, if you are looking for a smaller bag for the summer months to replace your larger, waterproof bag you use during winter/spring, I do not believe you should purchase the "small" version of this. Perhaps the "Medium" size is better, but it still does not solve the fact that the bag will rotate while you are wearing it, which is very uncomfortable to deal with while riding.

Again, this bag is great if you use it for something other than what I described. It would be a great "work" bag if you commuted by train or bus, or even walking. This bag is NOT great for legitimate bike commuters.
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on July 24, 2011
I just wanted to mention about the particular size of the bag I bought (small) since it was the hardest part for me when I was buying..

To begin with, I already have a huge messenger bag from another SF based company. And I still like the bag very much, yet it's a little uncomfortable at times, or looks silly when I have a notebook and a pen in a bag that can handle at least two 12 packs. For that reason, I eventually stop wearing it on a daily basis, and started using my backpack instead. But I really wanted my messenger bag back.. as it's so much more convenient and looks better IMO, esp. when you commute on bike.

So I decided to buy a small messenger bag, but Timbuk2 instead this time. The biggest selling point for me was how it had many small inner organizers/pockets, as well as its divider where you can separate your notepads, books, or small laptops (they are very practical for a college student like me). Also, I picked small because x-small looked a little TOO small and medium looked fine but knew I didn't really NEED that much space when I commute everyday cause I prefer to travel light.

Here's list of things I carry usually: textbook(s), notepads, bunch of pens, a mini stapler, an eyedrop, a 10" netbook or a 13" mbp, and a fleece jacket. (plus couple more small stuff). Well they all fit perfectly without trying and my back really appreciates the load and the way it sits securely on my back. If I don't put in my jacket, then I can stuff in a lot more; I just choose not to. You can also strap your jacket using the secure straps. I usually commute by bike or skateboard, and the bag always sits tight on my back. VERY comfortable if you know how to wear it properly. There's also a loop on the bottom front of the bag where I put a blinker on for night riding..

There's tons of favorable reviews on Timbuk2 products. I just wanted to let you know that small can be adequate enough for daily use, and feels a lot better than having a loaded big thing on the back. It also helps you to limit the things so you don't carry unnecessary things. My first Timbuk2, def. not my last one.
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on October 12, 2012
Pros:
Quality and Construction
Waterproof
Very spacious
Thoughtful manufacturing (quick release clasp and napoleon pocket)

Cons: Wish it sat less horizontally, more like Chrome bags. Just a preference though, very comfortable and appropriate

I bought the black medium and the gunmetal large to compare sizes. To see a variety of differences look at the customer images. I'm 5' 10/11", athletic build, and I have a t-shirt and 2 light hoodies on in the pictures. I'm keeping the large because they both ride well on my bike and might as well have more space. I used the black medium for delivering for a sandwich company for a few days before the large came in. I feel like the medium sits more horizontal and large more diagonal on my back. As a result I find that the large hugs your body more, which I find comfortable for riding around. Both bags have great construction and quality. Medium fits a 24 pack of coke snugly and it sticks out the top a bit. Large fits a 24 pack of coke to the brim of the bag and still have enough room horizontally for maybe a shoe or 2. Just rode for 4 hours in thunderstorms while delivering, it's very waterproof. You might get some spray in there from the flap gap, but it's minimal. Like I said in 4 hours of pouring rain it was dry on the inside, I got more droplets in it by opening it with wet hands than would have gotten in there just by riding around. Watch how you angle it or come up with a home made cover (I just used my hat), if that's not enough for you just complement the bag with a $10 drysack. The elongation clasp thingy is a great idea. It's pretty easy to take off without using it, but it's great for not having to fully take it off to put stuff in. Pockets are pictured, napoleon pocket is a clever idea for cell, wallet, dum dums, what have you.
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on September 1, 2016
Timbuk2's specialty are these messenger bags. No need to try any other! They are worth every dollar because they can withstand any weather and abuse. The velcro is the strongest I've ever seen. This company comes from San Francisco where bikers are hard core; they've done their homework. I only wish I would've bought a newer version with the inside loop for water bottles. The medium was the best size for me because in can fit an amazing quantity without feeling bulky. And even if it is emptier, it's comfortable. I recommend the Classic the most.
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on September 19, 2014
I ordered the small size. The overall quality of the bag is great from stitching to the material used.

The waterproof part of the cover help reduce water ingress to the bag but not eliminate ingress. This is because it is possible to for the cover not to completely cover the 2 sides. So if you have it cross slung as shown in the product image, That gap is facing 45 degree upwards. While the gap is small, under heavy rain, expect some water seepage.

The interior pockets are very useful but the design ought to be updated to cater for a 5 inch smartphone.

The shoulder strap material is also good but it's too stiff and cuts your hand. Compare to the crumple that I have, it uses softer material and is just as lasting.

My dislike that I have is for the 2 male quick release buckle & strap - which is not well tailored.
The strap is thinner and the buckle (size wrongly?) does not offer any grip and will slide freely with a slight tug along the strap. This makes adjusting the buckle to position fruitless/pointless.
I compare this to my Crumpler or Samsonite bag which the buckle fit the strap snugly and does not slide with a little tug

In this aspect, I expected something better given the price I paid for this bag.

Update: 1 year after my purchase

Usage once fortnightly at most & not for sports use. The inner waterproofing lining on the should strap is peeling.
This is something not expected for such a bag in this price range especially comparing it to the old crumplers I have that don't have this issue.
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on January 28, 2017
Great bag for a HS student. It is incredible sturdy, I love the durable Ballistic fabric. It doesn't seem to get very dirty. My son had a backpack last year, and all the pockets and sections are great, but they take up a lot of room! This messenger works much better for his needs. He said that it would be nice if it had an interior zipper for extra security (like as a carry-on, for example...not to use every day). Other than that it was the one he liked best out of the 8 bags I brought home for him to try!
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