Waterfield Rough Rider Messenger Bag – $335 to $355

WaterField Designs is a small studio operation in San Francisco, California, that was founded by Gary Waterfield in 1998. They make everything from gadget sleeves to handsome tote bags to Surface Pro covers, and their small, local operation allows them to quickly get multiple styles and sizes up and running (like sleeves for both Apple and Android devices), and they also crank out covers for random electronics like the Apple Superdrive, Apple TV, or even your wireless keyboard.


Waterfield Logo and Front Pocket

They also make some good bags, from a well-designed backpack to several different gadget pouches to the subject of this review, the Rough Rider Messenger Bag.

The black trim peeking out from under the flap.


The leather itself is from a (local to Waterfield) Sonoma tannery, and the bag is full-grain, slightly distressed, and scratches easily, in the best possible way. You can tell from the softness right out of the box that this bag will patina beautifully. The interior is unlined, allowing the softness of the leather’s underside to shine through.

You can see some character already starting to form ...

You can see some character already starting to form …


The bag is constructed from four large pieces of leather; three make up the bag itself (except for the sides), and the fourth is sewn onto the third (back to back) so that the inside of the flap is also the full-grain leather. The shoulder strap crosses under a second strip of leather to come off the bag at an angle, allowing the bag to fit against your body in a cross-body style very easily (however, if you prefer to sling the bag just over one shoulder, it will rest a bit awkwardly). The front flap attaches to the bottom with snaps, and there are two sets, allowing the bag to be stuffed more fully and still close. There is also a leather shoulder pad, and this is removable, depending on your preference.

A laptop, plus a view of the canvas pockets.

A laptop, plus a view of the canvas pockets.

The Rough Rider also has four pockets, though I found two of them to be in a curious location. On the inside of the bag, there are two waxed canvas pockets that are suitable for pens, cords, or some small goods; they could open far enough to accommodate my MacBook charger, for example. The other two are located on the outside of the front of the bag. They are almost a neoprene-like material (this is the color trim), so they are quite soft on one side. The other side backs up onto the exterior leather itself. On one hand, it is quite a shame to cover up the beautiful leather that is under the pocket. On the other, with the bag being fairly narrow, there is not exactly a plethora of space inside the bag, and the additional organization and storage is quite helpful. Once again, these pockets are quite narrow, but with the soft neoprene on one side, they are ideal for tablets, e-readers, or your smartphone. All in all, I would be curious to know if it was possible to make the bag slightly wider, put the second set of pockets on the inside somehow, and then let that nice leather be on the outside of the bag where it belongs.


The construction of the bag is very solid.  Even though there is not a rivet to be found, the bag uses sturdy thread throughout and I had no worry that the bag itself would not last as long any other.  However, there were a couple rough cuts on the bag, especially where the larger pieces of leather connected to the sides.  The sides were not burnished, which allowed me to see that the leather was not struck (dyed) all the way through.

You can see the glue, uneven corner, and difference shades in the layers of leather.

You can see the glue, uneven corner, and difference shades in the layers of leather.



iPhone (in sleeve), two notebooks, headphones, power adapter, and my MacBook.

The bag holds much more than its thin profile suggests. It will take a laptop, notebook holder, charger, pens, and a second book or two with no problems. It is not designed to be a bag for students or lawyers, but it is a perfect EDC size. I could load it up perfectly for a day of writing at my favorite coffee shop, and I also discovered that its size made for a handy “Daddy bag,” with the interior pockets helping me to keep the various necessary items for a day out with my kids organized and neat.

BestLeather Conclusion

The WaterField Rough Rider is a solid bag at a good price. It holds the right amount of things to make it a good choice in a fairly crowded field of challengers, and it has the added bonus of being constructed in (and using materials from) the USA. Check them out here.
Waterfield - Rear


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