Gear We Love: Rough Rider bag takes you through even the toughest commutes

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I’ve reviewed many a WaterField Designs bag over the years, and time and time again they come out on top thanks to quality, craftsmanship, and quirky highlight colors. The company’s Rough Rider Leather Messenger is no different: It’s the bigger, burlier, horizontal brother of the Muzetto, designed to hold everything from your 13-inch laptop to an extra pair of shoes. Just how burly is it? To truly test its rough-resistance, I took the Rough Rider to a place I’m loathe to take most of my nice bags: a roller derby tournament.

Steve Jurkovic

When bench coaching the #4 men’s roller derby team in the world, you end up needing a lot of gear in your bag. Some of it is traditionally technological: I had the requisite iPad and laptop, along with an external keyboard and a small bluetooth speaker. But also jammed into the bag were game-day snacks, wrenches, spare toestops and axels, bearings, pivot cups, helmet covers, wristbands, painkillers, emergency supplies, and more. My goal is for my bench bag to be the “break in case of glass” supply center—if something happens, there should be a solution in the bag.

At home games, I usually stuffed all these necessities into a recyclable-plastic Whole Foods bag—garish and heavy, sure, but it sat behind the bench and could take a beating. That wasn’t an option at the tournament: Not only were our games being streamed live, so I didn’t want to have a brightly colored shopping bag sitting on the bench, but we had to travel 1000 miles by plane to get there—a journey I wasn’t going to undertake with an overstuffed grocery bag.

So the Rough Rider got to take its inaugural ride stuffed full of goodies—electronic and otherwise—on a plane, in a car, and throughout a roller derby tournament. It came out of the ordeal without a scratch or a letdown. Based on my experiences with it that weekend, I’m willing to say that if life were a D&D campaign, this is as close to a Bag of Holding as you’re going to get.

Given that it’s crafted of leather, the bag expands remarkably well to hold all sorts of non-standard oddities in addition to your laptop, iPad, and technological fare. Its main compartment, which includes a thickly padded laptop sleeve, is hidden under a durable leather flap, with two waxed-canvas pockets lining the interior front. The outside front of the bag—accented in black, copper, flame, green, pearl, or pine—also offers two pockets, each lined with a soft, felt-like material and, according to WaterField, large enough to hold an iPad mini. Though I never stuck an iPad in there, the accented pockets often held an iPhone or other screened item, leaving the main compartment of the bag free to fill with assorted odds and ends.

The lack of a plethora of pockets and zippers may irritate some, but I actually enjoyed being able to dump most everything into one giant holding area—most of my bigger items had their own cases, and the smaller items either went in the few pockets that were available, or laid atop the rest. Without excess material for pockets and hidey-holes, you have more room to puff out the satchel to its full potential—and fewer extra layers of leather and other material means that the bag is lighter than you’d expect.

I really have only two quibbles about the Rough Rider. First, once you close the bag’s flap, there are no outside-accessible compartments. I often found myself wanting to stick a piece of paper or a set of keys in the bag, but I didn’t want to go through the hassle of unclasping the flap to get to the main compartment. A small outer pocket on the rear of the bag would have been welcome—though it also would have probably added to the cost of materials.

Which leads me to my second quibble: The bag is pricey. Note that I didn’t say overpriced: The materials are some of the best WaterField has put in a bag, and the thick leather, perfectly textured interior accents, and excellent craftsmanship all exude quality. But the price—$335 for the version for 13-inch laptops, $355 for the 15-inch model—may be hard to swallow for some. You’ll have to ask yourself if you need a bag as sturdy and cavernous as this one, when WaterField’s own Muzetto and CitySlicker are less expensive and expansive (and, of course, there are plenty of large bags from other manufacturers that cost quite a bit less).

But if you want the biggest and best, you’ll be hard-pressed to find a more impressive leather bag. It looks both professional and wickedly hip—even on women, despite its relatively large size—and it can truck around just about anything you think to throw into it. If you have the cash and need a good bag for trips, long commutes, or even roller derby tournaments, it might be just the thing you’re looking for.