Sponsored Links

Waterfield Designs Rough Rider leather messenger bag: Review and giveaway (Updated)

Steve Sande
Steve Sande|@stevensande|April 17, 2014 6:00 PM

Waterfield Designs Rough Rider Leather Messenger Bag

Over the past year or so, we've seen a trend emerging from high-end laptop bag manufacturers like Waterfield Designs and Pad & Quill -- use of leather as a primary material in their products. This not only provides a beautiful finish to the products, but also ensure that your purchase of a quality bag is going to last well beyond the expected lifetime of your laptop. Waterfield Designs recently introduced the US$335 Rough Rider leather messenger bag, and as you'd expect from this San Francisco manufacturer, it's functional, durable, and downright delicious to look at. Check out the review, then have a chance to win a Rough Rider.


  • Dimensions: 15 x 10.5 x 3.5 inches (38.1 x 26.7 x 8.9 cm)
  • Weight: 2.9 lb. (1.32 kg)
  • Materials: premium naturally-tanned distressed leather
  • Accent colors: black, copper, pine, green, flame, pearl

Design Highlights

The best way to describe the look of the Rough Rider is to quote some of the verbiage on the SFBags.com website -- "the clean professional look exudes a 'already been around the world a couple of times' masculine confidence". The accent areas are made with what appears to be ballistic nylon, but the primary material used is leather. The inside of the Rough Rider is unlined, but the leather shouldn't cause any abrasions on that nice aluminum finish of your MacBook Pro.

Also inside are two large pockets that you can stuff with accessories -- they are lined with waxed canvas. On the outside are two more large pockets into which you might want to place your iPhone or even an iPad mini. Those outside pockets are covered by the large leather flap that snaps closed to keep your stuff inside.

I've always liked the way that Waterfield Designs makes shoulder straps, and the Rough Rider's strap is no exception. It has a wide padded center that has a pebbled surface on it so that it doesn't slip off of your shoulder like some competing bags.

Anyone who is upset by the least little mark on something they own will obsess over the leather on the Rough Rider and should probably stay away from it. If you like your possessions to have that comfortable worn-in shoes look, then you and the Rough Rider are going to get along famously.

Update: We received information from Waterfield Designs that after this review ran, they received a lot of requests for a 15-inch version of the Rough Rider. That bag is now available for pre-order.

Functionality Highlights

What can I say? You can pretty much stuff a lot of equipment into the Rough Rider. While writing the review, I tossed my 13-inch MacBook Pro with Retina display, its power adapter, an iPhone 5s, and an iPad mini into the bag, and still had plenty of space left. Some folks might bemoan the fact that the four individual pockets lack any sort of closure (zipper, for example), but I find in most cases that those closures get in the way of searching for stuff in a bag -- something I find I'm always doing!

Case in point, one of the bags that I use on a regular basis has leather straps that go over two interior pockets. While I love that bag (not from Waterfield/SFBags) dearly, those straps drive me bonkers and I find myself looking for a pair of shears to cut them off.

The shoulder strap is comfortable, adjustable, and best of all, will not slide off of your shoulder. My other bag has a tendency to slide off, forcing me to either readjust the strap often or shrug my shoulder to get it back in place. Not so with the Rough Rider, which stays in place.


Gary Waterfield got his start as a San Francisco bike messenger, and he obviously put some of his practical experience into this classic and durable messenger bag. I've said it before and I'll say it again -- you get what you pay for. The Rough Rider might not be inexpensive (that's my only beef with the bag), but it is going to outlast a lifetime's worth of Apple laptops and accessories while looking better with age.

Rating: 3-1/2 stars out of 4 stars possible


Wow, this bag is nice enough that I almost wish I didn't work for the site so I could be eligible to win it! You don't have that problem, so all you have to do is enter for a chance to win a Rough Rider messenger bag. Here are the rules for the giveaway:

  • Open to legal US residents of the 50 United States, the District of Columbia and Canada (excluding Quebec) who are 18 and older.
  • To enter, fill out the form below completely and click or tap the Submit button.
  • The entry must be made before April 21, 2014 11:59PM Eastern Daylight Time.
  • You may enter only once.
  • One winner will be selected in a random drawing and will receive a Waterfield Designs Rough Rider leather messenger bag valued at $335.
  • Click Here for complete Official Rules.

Waterfield Designs Rough Rider leather messenger bag: Review and giveaway (Updated)