$355

A high-quality leather carrying case built to last.

I get ideas for product reviews from many different sources. I receive press releases from PR firms that are often willing to send me products to review. I also follow a lot of tech blogs and websites to stay up on the latest industry trends, and if I run across something that interests me I reach out to the firm. More often than not, I receive a review model.

A couple of months ago I ran across a review for a leather messenger bag. I had received an unbelievably gorgeous Vagabond Traveler leather briefcase/laptop case for Christmas that, in my opinion, is the leather bag to beat all leather bags. The reviewer in this article went on and on about the extraordinary bag he was testing, so I thought I would check it out. I reached out to the small San Francisco-based company that manufactures it and in less than a week I was unboxing my very own Rough Rider Leather Messenger Bag from WaterField Designs.

I was probably more excited about getting the Rough Rider than I have been about most other review models lately. I am a self-admitted accessory hound, so testing out a new bag is always a thrill. Over the years, I have reviewed several high-end messenger bags, including the Timbuk2 Commute 2.0, booq Cobra brief and TravelPro Crew Business Brief, but it had been a while since I added to the list. I was also intrigued to see if the Rough Rider lived up to the accolades so many other reviewers have heaped upon it.

Look & Design

When it comes to “designer” accessories such as bags and cases, pictures hardly do them justice. This was precisely the case with the Rough Rider. It, along with my Vagabond Traveler briefcase, are the only bags that have garnered comments from friends, colleagues and perfect strangers. The best way I can describe it is “modern-vintage”: the unfinished leather gives it an old-school look, but its unique strap system and clean lines lend it a very modern air.

WaterField Designs Rough Rider
Leather Messenger Bag

 

The Rough Rider and my Vagabond Traveler briefcase are studies in contrasts. The Rough Rider is very much a minimalistic bag. There is almost no hardware to speak of, except for the two snaps on the front flap. There are no zippers on the inside, either (more on this a little later).

I received a 15-inch model of the Rough Rider (there is also a 13-inch size) and its dimensions are 16.5 inches by 11.5 inches by 3.4 inches. Right out of the box, the bag also weighs in at 3.5 pounds. Some reviewers thought the Rough Rider was too heavy, but I guess that is a relative term. My Vagabond Traveler briefcase, with all its hardware and slightly bigger size, tips the scales at nearly six pounds. What you need to be aware of is that, given the amount of space the bag has, it is easy to load the Rough Rider up and make the weight uncomfortable.

Then there is the leather itself. According to WaterField Designs, the Rough Rider is constructed of rugged, naturally tanned, full-grain leather. If you have heard the term “smooth as butter,” that pretty much describes the feel of the leather. It is soft and pliable, yet not flimsy. It bears the marks of its daily usage, and over time I have no doubt it will develop a beautiful patina.

The unlined interior compartment is big enough to house a 15-inch laptop, along with its charger and cables, and much more. I have no problem packing in the plethora of books and binders I take to and from work. Depending on how much you stuff inside, the Rough Rider flap snaps securely shut with two options to adjust based on the bulk of its contents. Having gotten used to the strap closure system on my Vagabond briefcase, it took some getting used to the snap closures on the Rough Rider. However, adding a strap or buckle closure to the bag would completely change its look, so I understand the choice to use snaps.

It is worth pointing out that the interior compartment is not padded. Therefore, if you are carrying a laptop, you will want a padded sleeve to protect it. WaterField sells its Outback computer sleeve in a variety of sizes starting at $59. There is also no Velcro strap or anything to hold your laptop inside the compartment. Without any zippers of any kind, that would add a little peace of mind. Zippers on one or both of the interior pockets would be a nice touch as well, but that is more my own nitpicking than an actual flaw.

Inside the main compartment are two waxed canvas pockets. These are perfect for holding chargers or cables for a laptop. Under the flap are two more pockets, but these are lined with a plush scratch-resistant material that make them perfect for holding a device with a screen, such as a smartphone, mini tablet or e-reader. The nylon panel that makes up these two outside pockets comes in six colors, so you can customize your Rough Rider.

There is plenty of storage room in the Rough Rider, but it could have used a little bit more. The bag has no outside-accessible pockets, so you always have to unsnap the flap if you want to put something in the bag. It would be nice to have an easy-access pocket to drop my keys into.

The bag has a unique strap system: the heavy-duty nylon web strap is sewn to the bag and looped under two leather pieces on either side of the bag. That means the strap is connected to the bag at an angle. The advantage is that it helps maintain the bag’s slim profile when you are wearing it. However, it feels awkward if you are wearing it just over the shoulder; it is designed to be worn cross-body. There is also a removable no-slip shoulder pad for the strap. However, the strap itself is not removable, so if you are someone who likes to remove the shoulder strap, you do not have that option with the Rough Rider.

Lastly, there is a top leather handle if you do want to carry the bag like a briefcase.

Price

Now we get to what arguably will be the biggest sticking point for many consumers—the price. The 15-inch Rough Rider I received retails for $355. It is available only through WaterField, so do not expect to find any Internet deals. That being said, the bag is expensive, but not overpriced. In an increasingly disposable society, the Rough Rider is built to last. I thought I had received my “forever” bag for Christmas, but it seems I received another one in the Rough Rider. The materials are first-rate, as is the craftsmanship. Paying $355 for a bag may seem like a lot, but if I can get 25 years of use out of it that comes out to a little more than $1 a month.

Overall

I find that rating things like messenger or laptop bags is more difficult than true “hardware” such as phone cases, monitors or Bluetooth speakers. I try not to let my personal sense of style (or perhaps lack thereof) influence my overall feeling for the product. Already having one top-notch leather bag did not help my objectivity, but I did my best.

If I had not been using my other briefcase for these last six months, I would have said unequivocally that the Rough Rider Leather Messenger Bag is the nicest I have ever had. The quality of the leather and WaterField’s craftsmanship make this a truly amazing bag that will last you for many years.

As someone who often carries a laptop with him, however, I would not recommend it as a laptop bag. The lack of padding means you need your own computer sleeve, which you may or may not have. Even then, I am paranoid enough that the lack of an anchoring strap inside the main compartment makes me a bit nervous. In addition, the bag is not TSA-compliant. When I am flying for business these days, I prefer to carry a bag that fully unzips to lie flat through the X-ray machines so I do not have to remove my laptop.

However, if you are fortunate enough to be someone who travels without the weight of a laptop and are looking for a rugged, stylish and professional-looking bag for work or travel, the Rough Rider is well worth the money. As an added bonus, it is made in the USA.

Pros

• High-quality materials and craftsmanship
• Spacious interior compartment
• Two snap positions to accommodate the “fullness” of the bag
• Made in the USA

Cons

•  No interior padding to protect laptop
• No outside-accessible pockets
• Expensive

WaterField Designs Rough Rider 15-Inch Messenger Bag

$355 (available exclusively from WaterField Designs)