Timbuk2 FreeStyle Netbook Messenger Review

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I’ve looked for years to find just the right daily purse or gear bag.  I want a bag big enough to hold all my normal pocket stuff and the gadgets that I can’t live without, but I don’t want to spend so much money for it that I can’t afford to buy gadgets.  I have had an obsession with Vera Bradley bags for a while.  I like the fun look of Vera Bradley, but many of those bags are unstructured and don’t have organization pockets.  Lately, I’ve been in a minimalist phase.  I have a tiny little Vera purse, barely big enough to hold my wallet, keys, and phone.  That worked well until I got my iPad.  When I want to take my iPad along, I have to have a separate bag to carry the iPad or I have to stuff the iPad and my purse into a bigger bag.  After reading Julie’s recent review of her new vinyl Timbuk2 custom messenger bag, I thought a similar bag in a smaller size could be my perfect one-bag-fits-all solution.  I found Timbuk2 had just what I was looking for – the FreeStyle Messenger, sized for netbooks and ebook readers.

Timbuk2 had introduced the FreeStyle at the end of 2009, before the iPad was released.  However, if it’s designed to hold a 10” netbook, it should hold an iPad.  I was disappointed to see that I couldn’t customize my own FreeStyle.  These bags aren’t custom-made in San Francisco when you order; this style is actually imported.  The color combinations that were available on the Timbuk2 website were okay, but I was able to find a combination that I liked better from another online retailer.  I placed my order and had my bag in my hands in just a couple of days.

The FreeStyle bag is essentially their laptop messenger in an XS size.  The exterior dimensions are 12.8” wide X 8.85” high X 5.12” deep, and the bag weighs 1.67 pounds. The bag is made of ballistic nylon, and it’s lined with a waterproof TPU coating.  You can see the exterior of my bag is blue/black/gray.  The logo is done in red embroidery.  I was happy to see that the TPU interior coating is white; things are hard to find inside a dark-colored bag.

The bag has a 1-7/8” wide black webbing shoulder strap.  The strap is very firmly sewn on.  One end has a thick, sturdy plastic D-ring at the bottom so you can clip on small bags or accessories.  The other end of the strap has the quick-release buckle so you can easily adjust the strap length.  The maximum drop for the strap is about 18 inches.  This strap is stiff, with a rather “sharp” edge.  It came with a coordinating strap pad in the blue nylon.  The pad wraps around the strap and has a Velcro closure; it is 11.5” long and has a dense padding inside.  This padding makes the strap pad rather stiff, but it does keep the strap from “sawing” at your neck while you wear the bag.

A big, glaring omission from the FreeStyle bag is a grab handle.  I would really prefer this bag – and all messenger and backpack-style bags – have a grab handle.  Also, there is no Cross Strap with this bag.  The Cross Strap is used to stabilize larger messengers on your back, but a bag this small doesn’t really require one.

The front flap closes with two heavy-duty plastic clips.  The tails on the adjustable straps for the male ends have reflective plastic patches with the Timbuk2 logo.  Under the flap, there are two strips of Velcro for extra security.  The Velcro is very strong and makes a lot of noise.  (It’s loud enough that it startled a man in the coffee shop in a busy Barnes and Noble bookstore.  He was sitting about 8 feet away from me, and he was listening to music through earphones when I rrrriiiipppped open my bag.)

Note the loop of excess strap on the side of the bag (left). You can also see an adjustment buckle hidden inside the loop.

The back of the bag is plain.  There is no slip-in pocket.

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Under the front flap, there are two pockets.  These are the width of the black band.  There’s a zippered pocket in front; inside is the sewn-in red key tether.  The zipper pocket is just big enough to hold my keyring with my over-sized car key.  Behind the zipper pocket is an open pocket.  This pocket is about 4.5” deep; I use it to hold the two straps for my camera.

Netbook pouch with my added padding (top), organizer panel (bottom)

Inside the bag is a large organizer panel on the front wall.  This panel has a total of ten storage slots and pockets.  On the front, there’s a large pocket with a flap with a Velcro closure. This pocket could hold a larger smartphone, but I have a bottle of hand sanitizer and another small bottle in there.  Beside it are two “stacked” slip-in pockets made of a soft, flannel fabric.  My LG enV3 phone fits perfectly inside the back pocket.

Behind these pockets is a zippered pocket.  This pocket extends the full length and width of the organizer panel.  I have a wallet, checkbook cover, pen, and a few other small items in there.  Inside this pocket are 4 credit-card pockets and three deeper pockets.  You can just see the credit card pocket above the red card case in the above picture.

There is a padded, closed netbook pouch on the back wall.  It’s sewn into the bag’s side seams, but it is completely free at the top and bottom.  The pouch is covered by a flap; it’s held closed by Velcro.  The pouch has a thin padding and is lined with a red, fleecy material.  There is more than enough room inside for my iPad encased in the Belkin Grip Vue case.  The iPad in the Belkin is almost the same width as the netbook pouch, but there is extra depth available.

Because the padding in the netbook pouch is thin and there is no structure or padding on the back wall of the bag, I decided to add some padding along the back wall.  I slid a piece of dense foam between the netbook pouch and the back wall.  I put my iPad into the pouch with the screen facing the back wall.  I feel this arrangement offers the best protection for my iPad screen while it’s in the bag.

You can just see the piece of dense foam I added behind the iPad sleeve.

I have a lot of stuff in the bottom of my FreeStyle bag.  There’s a medium-sized digital camera (in brown polka dot case), an iPod touch in a Vera Bradley Tech Case, a Plantronics Discovery 925 bluetooth headset in its pink charging case, a folding mirror, a couple of bottles of OTC meds, a Vera Bradley card case, my Arctic Cooling E361 earbuds in their case, comb, and my sunglasses clip-on in its case.  There’s still plenty of room inside the bag for charging cables and other things.

Complete contents of the bag

Fully loaded with the iPad, the Timbuk2 FreeStyle is heavy.  If you wear it on your back as shown on the Timbuk2 website, the bag is surprisingly light and comfortable.  My daughter Rachel is modeling the bag for me.  For reference, she is 5’1”.

I like the Timbuk2 FreeStyle messenger bag, and it’s going to be my daily bag now.  I do wish the strap were a little softer and narrower, but the strap pad does help protect my neck.  I like the color combination I found, but I do wish I could have completely customized my bag.  I would have loved a black/navy/green bag.  The one thing that I really, really miss is a grab handle.  Add a grab handle and make the shoulder strap out of seat belting, and the bag would be nearly perfect.


After I wrote the review, I have been carrying the FreeStyle every day. I love the organizational features of the bag, and it really is the perfect size for all the stuff I carry daily.  But because I really, really miss the grab handle and because the shoulder strap is wide and scratchy, I found myself regretfully thinking of putting the FreeStyle aside and trying to find another bag.  I decided to try an experiment with the shoulder strap before giving up, and you’ll see the result in the picture below.

I simply shortened the strap as much as I could – until the strap pad was laying flat across the top of the bag.  This left me with a very long loop of strap hanging down off the side of the bag – sure to get caught on everything I walked by.  I used the adjustment buckle (hidden under that hinged adjustment lever) to shorten up the loop of excess strap.  This resulted in a “cinnamon bun” loop sticking out from the side of the bag.  I then tied a strip of elastic cord (originally used to attach the product tags on the bag) around the loop to make it as tight and flat as possible.  I absolutely love using the bag this way.  The strap pad makes a very comfortable handle to hold in my hand or to slide up onto my arm.  I consider this my Birkin bag for the gadget girl. 😉

None of these adjustments are permanent, so I can easily convert it back to a messenger bag when I need to have my hands free.  I find the FreeStyle bag has moved just a bit closer to “perfect” for me now.


Product Information

  • Good size for a daily gear bag
  • Lots of organizational pockets
  • Available color choices allow you to go more casual or more business-like
  • No grab handle
  • Shoulder strap is a little wide and stiff
  • Can't customize your own bag in this size

7 thoughts on “Timbuk2 FreeStyle Netbook Messenger Review”

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  2. Good review, personally I tend to like a separate sleeve in my bag. Did you also check out the X-small classic messenger bag? With the Slash pocket and the Grab strap, the only issue would be the shoulder strap. But you do get to choose from 4 styles of strap pads(10-20$ extra).
    There is a Laptop Loveglove option but it appears to be only offered for the Small size to the Large size classic messenger, skipping the smallest and the largest.
    Personally I’m saving up for a Medium with Slash pocket(if I ever get a new laptop).

  3. @deanS I didn’t look at the X-small bag because I wanted the integrated sleeve for the iPad. I wanted the smallest bag they had in the messenger style that would work for my iPad, so I decided to go for the FreeStyle. I do wish I could have customized my colors, though.

  4. I’m one of those anti-Timbuk2 folks, as I had one (well, still have one, I suppose), but have since found better messenger bags out there.

    Here are my biggest complaints about the bag.

    1. The top cover flag is not large enough. It just doesn’t fully cover the edges of your bag, which means that in a rain storm, water easily get inside your bag.

    2. The front flap velcro requires too much precision to line up all the time. This is really noticeable when you stuff your bag in a lopsided fashion, so that the flap does not lie perfectly in front, but off to one side. When it does not align properly, it means the front flap only stays down due to gravity.

    3. The shoulder pad stinks. It is not comfortable – the padding is too thick, and it does not have enough give it in. Worse, the padding likes to slip off your shoulder, because it’s made of slippery nylon.

    4. It doesn’t stand up. It looks like it should stand up, but the design of the bag makes it want to lean, so you are forced to prop it up against something.

    As you can tell, I experienced honest to goodness problems due to each of these issues in the past. There are other issues I have with the bag, but those are the big ones.

    The one good thing I can say about Timbuk2 is that they introduced me to the world of messenger bags, and I have since realized that they are one of the “low end” manufacturers.

    If you really want a nice messenger bag, check out BaileyWorks bags at baileyworks.com. I have one of their small courier bags, and pretty much all my gripes went away.

    For example, in the BaileyWorks bags, the top flap is larger on the sides, so that it it does a much better job at keeping water out of the bag. The fuzzy velco is a long horizontal strip on the front, while the hooking velcro are vertical strips – this allows for the vecro to stay closed, no matter how awkwardly you stuff it. The shoulder strap does not slip and is extremely comfortable – only my expensive guitar straps rival it in comfort. And the bag has a slight pyramid style design, which means it likes to naturally stand up when you put it down. I could go on, but I’m starting to sound like an infomercial.

    I’m sure there are other courier bags just as good as BaileyWorks out there, but BaileyWorks was the first one I found that was a clear upgrade to Timbuk2, so I’ve stuck with them. Now if only BaileyWorks sold one in a nice brown leather…

  5. I have the XS Classic Messenger bag from Timbuk2, which is only different from the Freestyle in the slash pocket where the iPad goes -the Classic does not have the flap closure- and the side-entry Napoleon style pocket in the front which is really handy. Other than that, the dimensions are exactly the same.

    I have to say that I absolutely love my bag. It is tough, rugged, and holds lots of stuff. Although the shoulder strap was stiff at first, after only a couple of moths of use it softened up tremendously. I now hope for the actual bag to soften as much as the strap did. I went to the Timbuk2 store in SF the other day, and the girl working said if I lightly wet my bag with a rag it will begin to soften. I haven’t tried it yet, but will report back once I do.

    I highly recommend this bag to every iPad owner.

  6. I always remove all the Velcro (hook-and-loop) fasteners from these bags whenever I buy one, because of the rrrrrrripping sound when you tear them open. The clasps are enough to keep the things closed.

    Only complaints? The shoulder straps are WAY too wide. And… the things are quite heavy… even when empty.

  7. I have the same bag and I have been using it for 6 months. I think its great for ipad owners and couldnt think of any other bag that works as well as the timbuk. I want to soften the balistic nylon more. I have a larger timbuk bag and its pretty soft. If I wash it over and over again could this soften it?

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