I recently purchased a new piece of luggage. I’m traveling a lot more than usual this year and needed something a little more versatile than my existing rolling bag.
As stated in a previous post, I’m not a big fan of rolling bags. I think our reliance on convenience has led many of us to underestimate our potential. Biking 20 miles, doing a pull up, running a 5k, or carrying a 15 lbs piece of luggage 1 mile through the airport are all attainable by any reasonably committed individual. In any case, my stubborn insistence that not everything in life should be easy led me toward a piece of carry on luggage that favored utility, durability, and style over convenience. Carry on here is used in the literal sense, in that I would “carry it”. The piece in question ended up being a Saddleback Leather Waterbag. I spent a week trying to decide between the Waterbag and the Duffle bag, and eventually settled on the Waterbag. I felt the layout of the bag was more flexible and would enable me to stick with it as my primary travel bag in more situations. It has a high degree of expandability as well as flexibility. What follows are my impression after traveling to Orlando Florida for a 4 day business trip.

The waterbag sitting on my ottoman
Durability and Style:
The bag performed admirably. It’s rugged and durable. I don’t feel like the bag needs to be babied. If it’s dropped or drug, the resulting scuff marks only serves to make the bag look more remarkable. In most cases you can simply brush the dirt off and the bags inner beauty starts to shine through. It’s made from one single piece of leather, with only one major seam. It looks like it might require an entire cow to get this one piece of leather.
The curve in the major seam on the front of the bag serves as a nice stylistic touch. It adds a big of organic flow to the design. Saddleback has done a good job of letting the leather speak for itself. There is very little in the way of adornment on this bag. Everything other than the swoop of the stitching is functional first, and stylish due to it’s rugged form-follows-function design principals.
I went with the Dark Coffee brown color to match my messengers bag and the color is deep and rich. Since Saddleback uses leather that is dyed all the way through scratches don’t show up nearly as bad as with cheaper leather. My messengers bag has lightened up some in color over the last few years, but the weathering is showing up more where the leather is stretching some based on how I’m using it. It’s not a negative though, the resulting color shifts in the leather give the bags character, not at all like the cheaper leather bags often used as laptop cases.
Flexibility:

The backpack configuration is great for higher mileage or heavier weight.
I appreciate the flexibility built into the size of the bag. There are two rigid inserts that come with the bag, one that is 6 inches tall, and another that is 9 inches tall. I only needed 4 changes of clothes and was able to fit all of those in the bag as well as 50 or so product brochures for the trade show I was attending. while using the 6 inch insert and with room to spare. The bag can be flipped from an “over the shoulder” configuration, to a backpack. If the load starts to get heavy, this is the best way to travel without wheels and without destroying your back.
I wrapped the center strap over the top handle and used the attached leather handle to carry the bag when it wasn’t slung over my shoulder. This is the same way it is setup in the picture above. In this configuration the bag is fairly watertight. On my walk home during an unexpected 60mph wind storm that everything inside stayed dry. My jeans however were another story.
If water-resistance isn’t an issue changing the bag to use the 9 inch insert and leaving the top a little less tightly sealed I could easily fit 6-7 days worth of clothes in this bag, enough to travel for a week or so by myself or 3-4 days with a friend.
I didn’t have an opportunity to try it in the backpack configuration. I almost always use my messengers bag in this configuration and once you get comfortable swinging it over your shoulder it is actually quite convenient. It’s worth noting that the included strap is a little short in the backpack configuration and might not be suitable for larger guys.
Usability:
On my way through security I definitely felt rushed trying to unbuckle all three straps. In the future I will unstrap the 2 outside straps while in line. As the leather softens this will get easier as well. When the leather is stiff it can be a little tricky to get it the straps buckled. My messengers bag suffered from the same problem for the first few months.
On this most recent trip I also traveled with my messengers bag, and in the future I am going to avoid that. With a few additional pouches for my laptop and other assorted tech gadgets the waterbag would have had plenty of room and the simplicity would have been welcome. Trying to carry both the waterbag and the messengers bag ended up being a bit of a juggling challenge. Using the messengers bag in the backpack configuration and slinging the waterbag over my shoulder was doable, but a bit tricky at times. Next time I will likely setup the waterbag as the backpack and carry the messengers bag by hand.
Negatives:
The main drawback of the bag is really the weight. If you are going to consider carrying this bag be prepared to build up a few calluses in the process. The bag didn’t end up feeling as heavy as I had feared. The external handle is a little firm and I’m hoping it will soften up over time. That said, I often slung it over my shoulder.

Roadtrip!
What’s next:
With the various buckles and d-rings riveted to the bag I’m excited to strap it on the back of the motorcycle for a weekend trip. Even in the rolled configuration it has more storage space than the top case I usually have on the motorcycle. I’ll probably bring a plastic bag to use in case of a downpour, but the bag is waterproof enough that it should survive the occasional squall.
Conclusion:
This is a great bag, and so far I’m thrilled with my purchase.