Rough Rider by Waterfield Design

Waterfield Design's Rough Rider Leather Messenger Bag has been a fan favorite for a few years. Recently, the stylish bag received a design update, so it now comfortably fits the 15-inch MacBook Pro, has two dedicated slots for your Apple Pencil (and your other favorite stylus), and has a back handle so you can anchor it to your rolling suitcase. It also now comes with six different under-flap colors so you can customize your accent color. It's big enough for all your mobile computing needs and makes you look like an adventurer/archeologist/professor.

Rough Rider Messenger Bag


Price: $429

Bottom line: The Rough Rider Messenger Bag is a gorgeous gear bag that's definitely big enough to fit your laptop, iPad, portable battery charger, wall plug, cables, and more. At 3.5 pounds, though, it's not exactly a lightweight option.

The good

  • Really good looking
  • Deep main pocket (3.5" deep)
  • Padded separator sleeve
  • Unique design to help disperse weight off the shoulder
  • Handheld or shoulder option
  • Suitcase anchor strap

The bad

  • Heavy
  • Expensive

Rough Rider by Waterfield Design

Rough Rider Messenger Bag: What I liked

First and foremost, I love the way the Rough Rider looks. Always have. It hits all of the business adventurer style buttons that I like. I grew up loving Indiana Jones, and it's no coincidence that I love a messenger bag that looks like Dr. Jones would have toted it to one of his archeology classes.

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The Rough Rider has a main pocket that's about 3.5-inches deep, which is a very nice sized pocket. One issue that most laptop bags have is that they don't have a lot of extra room for all of your cables, portable batteries, and the like. The Rough Rider is designed so that you can slip your laptop into a padded sleeve, slip your iPad into a padded front pocket, and shove pretty much everything else you want to bring with you in the main pocket.

I easily fit my 13-inch MacBook Pro, my iPad Pro, my mophie powerstation AC, my power cables, my portable USB-C hub, and more inside. If I'm planning on having some relaxing time, I'll throw in my Nintendo Switch, too.

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The bag is designed with an angled shoulder strap that acts like a compression strap. It holds the bag against your body to keep it from bouncing around while you walk. It also has a wide, non-slip shoulder pad, which disperses the weight so it doesn't feel quite as heavy.

You can wear the Rough Rider on or over your shoulder like a typical messenger bag, which I love because I can keep my hands free for eating ice cream (or whatever). But there's also a small strap on top of the bag so you can carry it like a briefcase. This is a nice bonus for when you need to grab your bag and go. You don't have to throw it over your shoulder if you don't want to.

The suitcase handle on the back is a really nice bonus feature. I wish all bags came with this little strap. It makes it possible for you to have your personal bag and carryon suitcase connected together.

Rough Rider by Waterfield Design

Rough Rider Messenger Bag: What I didn't like

The Rough Rider weighs about 3.5 pounds. As a comparison, the 13-inch MacBook Pro weighs just over three pounds and the 15-inch model weighs just over four. The Rough Rider essentially doubles the weight you're carrying in the bag alone.

I tried carrying it with me to WWDC and after just a few hours regretted the decision to use it as my walk-around bag. It's definitely not a good convention gear bag. If you're toting your gear to work and back and don't have long walking distances between destinations, it's probably fine, but it is absolutely not for long-distance carrying.

It's also important to note that the Rough Rider costs $429, which is nothing to sneeze at. By comparison, the MacBook Air costs $999, so you're spending nearly half that just on a bag to carry it. It's a high-quality, well-made bag and worth the price for something that could be your forever-bag, but it's a costly investment.

Rough Rider by Waterfield Design

Rough Rider Messenger Bag: Bottom line

I love the Rough Rider and I love walking into a coffee shop looking like I just walked off the Millennium Falcon. The more you use it, the better the leather patina gets. It's got the look, for sure.

4 out of 5

It's built for laptops as large as the 15-inch MacBook Pro and has padded compartments to keep your gadgets safe. The 3.5-inch deep pocket allows room for charging bricks, power plugs, cables, and a whole lot more.

At 3.5 pounds, it's a heavy gear bag and not something you'd want to use as an all-day carrier at a convention. If you're commute doesn't include a lot of walking, it's a sturdy case that could potentially become your forever-bag, which is good considering how much you have to invest in it.

$429 at SFBags

MacBook Pro


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