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Review: The Rough Rider Leather Messenger Bag By WaterField Designs

Review: The Rough Rider Leather Messenger Bag By WaterField Designs

March 18, 2014
We absolutely adore iOS and Mac accessories from San Francisco, Calif.-based Waterfield Designs. The company's latest product is the Rough Rider Leather Messenger bag. How does it hold up? It's time to find out.

The Facts

  • Company Name: WaterField Designs
  • Product Name: Rough Rider Leather Messenger
  • Price: $335 for the 13-inch model and $355 for the 15-inch model
  • Size: The 13-inch Rough Rider measures 15 inches by 10.5 inches by 3.5 inches, while the larger one is 16.5 inches by 11.5 inches by 3.5 inches
  • Compatibility: Has enough space for one laptop and one large-size tablet. Plus keys and a mobile phone, and other small accessories.
  • Website:
  • Date Reviewed: March 18, 2014

The Basics

The Rough Rider is ideal for both casual and professional office environments. It can also work as an overnight bag for those who can pack light. It is made of premium, distressed leather, which almost certainly looks better with age. The bag comes with four deep pockets, two on the inside that are lined with waxed canvas, and two under the flap made of scratch-free material in the color of your choosing. At launch, the accent color choices are black, copper, pine, green, flame, or pearl. The leather flap on the Rough Rider snaps together using two of four buttons, two on either side. This allows for an adjustment, depending on the size of the bag’s contents. The Rough Rider can hold any laptop up to 15-inches, including the MacBook Pro or MacBook Air, plus a tablet, smartphone, and other digital gear. Take a look:

Integration with iOS devices

For testing purposes, I’ve been using a flame-accented Rough Rider with my 11-inch MacBook Air, 9.7-inch iPad Air, and iPhone 5s. Additionally, I’ve carried around a PlugBug charger from Twelve South. I found there to be plenty of room left for a protein bar (or two), a regular notebook, and more.


The Rough Rider comes with one non-detachable black nylon strap.

Use and feel

This bag combines style and ruggedness with ease. Waterfield Designs claims this combination exudes an “'already been around the world a couple of times’ masculine confidence,” and they are correct.

Scratches, scuffs, and dirt

The more scratches and scuffs, the better, in my opinion. Still be sure to use a leather cleaner on it occasionally.

What’s Hot

  • Durability
  • Plenty of pockets and color accent choices
  • Stylish
  • Designed and made in the United States

What’s Not

  • Some might be turned off by the Rough Rider’s price
  • Perhaps the strap should be leather too

How does it stack up?

Waterfield Designs has scored another home run with the Rough Rider. I have yet to find a messenger bag this stylish and practical.

Where can you get it, and how much does it cost?

The Rough Rider is available for $335 through Waterfield Designs. The next product run deadline is March 30.

Our Advice

Each time Waterfield Designs sends me a product to review, I worry it won’t be as nice as the one before it. No worries here, as the Rough Rider is a winner. As far as the price goes, I believe it is justified. The bag is nearly all leather and it is designed and made in the United States. Besides, I've seen bags of similar style cost a lot more.

The Rough Rider’s Overall Scores:

Aesthetic Appeal: ★★★★★ Wow Factor: ★★★★★ Build Quality: ★★★★★ Value: ★★★★☆ Buy Now: You may purchase the $335 Rough Rider at this link. For other reviews on products from Waterfield Designs, see: Review: Outback Solo Is The iPad Bag Indiana Jones Would ChooseThe New Staad Laptop BackPack Is Perfect For The Techie In Your Life, and Review: Get Smart With WaterField Designs' Secure And Stylish iPad Smart Case.

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