Review: Timbuk2 Freestyle Messenger Bag


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If you are looking for a compact messenger bag for your iPad, then this may be an option for you. The Freestyle Messenger bag from Timbuk2 is a smaller version (XS) of their classic messenger bag and comes in four colors. This bag is not a custom build bag like their others which means it’s already ready for you.

It has a main flap that closes the bag off. You can secure it by just the Velcro or also with the clips. While the flap does cover and close the bag up, it’s not sealed 100% but it will still offer great weather or outside protection. The bag is nylon on the outside but it has a waterproof TPU liner inside.

There is a little pocket that has a zipper on it under the flap. In this you will also find a red tethered key holder.

Inside, you have more organizational options.


There is a padded soft interior sleeve for your iPad. (It says it will fit an iPad2 with the smart case, but I am not able to test that out.) It will fit an iPad, but unfortunately, not one where you may have a case on it. It’s designed to accommodate essentially a naked iPad (or netbook, kindle etc). If you prefer to use keep a case on your device like me, don’t let that deter you, as there is plenty of room in the bag to accommodate it. I stuck my iPad behind the sleeve when I had the Apple case on it. For larger cases, the iPad will fit in the middle.

There is another zipped pocket where you can store other goodies. Inside this area you will also find some pockets that would accommodate credit cards, notes, and things of that nature and size.

Outside of this zippered area, there is another pocket with Velcro flap and a couple smaller pockets.

The strap is adjustable, but it’s also stiff. This may change over time.

Check out this video.


This bag offered me a love hate relationship. I loved the compact size of this. Even though the sleeve did not accommodate my iPad with my cases, there were other options and space for me inside to use. This is plus anyway. The bag was small enough to carry my essentials to the coffee shop or out and about, and yet still offered some extra space. It organized my junk very well, and I love the looks of it. The review sample I was using is the color  black / gunmetal / limeaide.

The part that I did not like was the strap. I wish the strap could be switched out with a longer version, as it was too small for me. Sure if I wanted to carry it like a purse, it worked fine. But it was too small for me to wear cross body, like many messenger bags are worn. That’s how I like to wear a messenger bag.  To be fair, it looked fabulous on my son. I let him use the bag also and it looked like a perfect fit for him. Since the strap was too small, one of the methods I did was to shorten the strap and use it as a carry handle. (Note that this bag does come with a removable shoulder strap as well).

Besides the strap, I really liked the bag. There is excellent construction and durability designed into the Freestyle.


Specs and features:

-Fits the iPad and iPad 2 with Smart Case.

-Durable ballistic nylon exterior.

-Fuzzy Tricot-lined internal sleeve for protecting 10" netbooks, iPads and Kindles.

-Built to fit 10" netbooks.

-Waterproof TPU liner.

-Adjustable cam buckle makes it easy to strap on and off.

-Internal organizer.

-Red key tether.



Product Page:




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