One of our hosts upstate this weekend recently bought a city bike in part to make trips to the market in the town center. As he was using a tote bag to port his wares, discussion eventually turned how best to bring home his purchases and the pros and cons of a messenger bag. I went through a rather exhaustive search a while back and ended up buying a medium BaileyWorks Super Pro Messenger Bag which has turned out to be a really good purchase.

BaileyWorks Super Pro
I have a Deuter backpack that I use the days I race which is phenomenal, very comfortable and it handles a lot of gear. Unfortunately, the backpack ends up in my son’s face when he’s on his child seat given the relatively short chainstays on my commuter, an Il Pompino from On One. Thus when it came time to search for a commuting bag, I needed a bag that could sit a little higher and more evenly distribute the load across my back. Enter the messenger bag.
The Bag
I decided on the BaileyWorks after a friend turned me on to them and some frustrating research looking for the perfect bag which just doesn’t exist. The Super Pro has a cordura shell and a vinyl-coated nylon waterproof lining. The large front flap comes with a reflective strip as well as a clip for a light (for a little extra you can get yours without these features, although I’m not sure why you’d want to do that). Lift the flap and you’ll find ample cargo space and many pockets. The most distinctive feature on the Super Pro is the split-strap which makes the bag easy to get on, easy to swing around and easy to get off. The Super Pro also comes with a third-leg, a strap that connects from the back of the bag to the main strap to stabilize the bag and ensure it doesn’t swing forward while you’re riding.
The Good
There are four critical things in looking at a commuting bag. How easy is it to get on and off? Does it stay in place? How comfortable is it when it’s loaded? And how easy is it to keep stuff organized? For the most part the BaileyWorks Super Pro has you covered.
Because of the split-strap, getting a snug fit or loosening the strap to get it over your head is as simple as pulling on an o-ring. I’d explain it in more detail, but this video from the BaileyWorks website shows you everything you need to know.
What’s more, the strap is reversible so the Super Pro swings both ways (i.e., no need to worry about left-swing or right-swing, you can change if the need ever occurs).
The third leg keeps the bag in place when you’re riding, so there’s no worrying about the bag swinging forward and potentially knocking you off the bike. The padded element where the strap connects to the bag at the shoulder lets you get the bag nice and snug while keeping the strap from digging into your shoulder.
With so many pockets, it’s easy to keep all your gadgets where you want them. The two velcro-flapped pockets in the front of the bag are large and deep. I’ve got my tools/tubes, etc., in one and I can even secure my u-lock under the flap. The other pocket comes with a pen-holder so I use that for my phone, pens, wallet and glasses, all of which fits. On the right side there is another deep pocket which can store a water bottle if so inclined (for a little extra you can get an identical pocket on the left side, but I’m not sure you need it.) Inside main compartment, there is a zippered pocket which I use for keys and two side pockets, which are deep.
One thing that I don’t think matters is how much you can fit in the bag because you can always buy a bigger bag. And in fact, as with most things in life, I’ve never heard anyone say, “Gee, I wish I got the smaller one.” The medium bag holds quite a lot, and while I can see the need to hold even more, the large bag is really, very, very large and so I couldn’t see using it as a post-ride walk around bag to the office. Interestingly, BaileyWorks measures the capacity of their bags in terms of the number of beer cans it can hold. In the case of the medium that number is 68, as you can see here:
What’s missing?
The main compartment is just that, a main compartment with no dividers which is great if you just have a lot of gear to haul, but is a bit of a nuisance when you have papers, a laptop, pads, etc. If you are using the bag for commuting, you’ll want to consider getting some zippered folders so you can make organization a little easier. I opted for the optional interior divider which is good for putting loose papers in although again, I ended up with zippered-folder. It would have been nice if the pocket created by the interior divider could be padded and zippered, but BaileyWorks won’t do that because adding a zipper or stitching the padding in place would require compromising both the lining and the shell of the bag.
The biggest issue with the Super Pro is that you trade a little comfort when you have odd-angled or very hard items inside. Granted I’m comparing it to my Deuter which is designed to keep the actual bag off my back, but I’ve taken to wearing my kryptonite chain-lock around my waist because it can be uncomfortable inside the SuperPro. I also found that when I was toting my 17” notebook around, there was no good way to keep the notebook off my back, as there is no padded compartment for a laptop. A laptop shell did provide some relief, and you’ll want that anyway, as it’s a good way to keep your laptop separate from the rest of the stuff you put in the main compartment. The same holds true for all the laptop accessories (i.e., power supply, plug, USB cables, memory sticks). And while BaileyWorks won’t put padding in the bag, you can buy some padding and put it into the pocket created by the rear divider and thus your comfort issue is solved.
The Final Analysis
Overall, the BaileyWorks is a tremendous bag and worth the price tag. Despite the minor comfort issue, its capacity, ease of use, ability to stay in one spot and its durability easily make it a bag worthy of the commuting cyclist. I’ve found I’m now using my bag for pretty much everything, even carrying diapers, a potty, and changes of clothes when I take the kids to the park. I’d give the BaileyWorks a 4 on a scale of 5, but I honestly think only a Deuter-type backpack could score higher. And with a capacity of 68 or 66 beers, you’ll always be the hit of any party.
That’s today’s view from the back.
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I really want to purchase a Bailey Works bag. I am in law school, and will use it to carry mostly big text books and my laptop, and would like to use it for my summer externship. So I am thinking about a 253 (black). I don’t know what size to get though. I don’t want it to be so big that I look ridiculous at work or school.
Will the medium accommodate my laptop plus 3-4 big books? Or do I need to spring for the large. Does anyone have photos of them being worn, or side by side? I can only seem to find pics of the super pro.
Thanks in advance!!