Waterfield Designs Rough Rider leather messenger review

Sections: Cases / Bags, iPad, iPhone, iPhone/iPod touch/iPad, Laptops, MacBook, Macintosh/Apple Hardware, Peripherals, Reviews

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Rough Rider Leather Messenger

Waterfield Designs has become the go-to option for owners of Apple devices and other tech products. The San Francisco-based company continues to provide high quality, excellent design, and superb customer service during a time when many companies are mass producing low quality products. Waterfield’s latest product, the Rough Rider Leather Messenger is all about maximizing space and carrying all of your digital devices in style. The Rough Rider is made out of very high quality leather and waxed canvas (two of my favorite materials for products like this), and when you’re walking around with the bag (or running for the bus or train) the strap system keeps all of your stuff close to your body so it doesn’t move around too much. This was especially handy when I had my Macbook and other devices in the pockets.

The Rough Rider Leather Messenger offers an excellent solution to carrying all of your digital gear along with items such as magazines, clothes and books. It is available in one leather color but has six different accent colors: Flame, Copper, Black, Green, Pearl and Pine.


The Rough Rider has one of the best designs I’ve ever seen on a bag because of the naturally-tanned all-leather design. The bag came out of the box with what Waterfield calls an “already been around the world a couple of times” look. It will only continue to pick up more scuffs and scratches and will develop a nice patina over time, which will add even more character.

The edges of the Rough Rider are raw and natural, which gives this bag a true “messenger” look. It is as if the bag is calling back to its name and something very historical, such as when Theodore Roosevelt and his Rough Riders took San Juan Hill. The interior of the bag is un-lined, which I think adds even more style, even though it isn’t visible to the public. I think that this harkens back to Steve Job’s ideology of designing the inside of a product even if no one can see.

Rough Rider Leather Messenger

The flap on the bag closes shut with two buttons, adding flair and authenticity to the messenger, though I do think adding a magnet or an internal clasp would have made the bag a bit easier to open and close. In the product video, Gary notes that the Rough Riders are sewn on a circa-1940s machine that is strong enough to sew a penny through leather.

This shows through in the stitching of the bag, which is very strong and keeps together all of the tough pieces of leather.


I had quite some time to use this bag, and it only got better with age. The leather has started to pick up a number of scratches and marks, and I can literally point out all of the places I’ve been with it. I think this is what separates a Waterfield Rough Rider from another mass produced messenger bag—the fact that it has a story and a certain uniqueness to each person who owns one.

Waterfield Designs Rough Rider leather messenger

Currently, I own a messenger bag that uses a very slippery strap, so it causes the bag the wildly fly about when I’m walking quickly or running. The Rough Rider stays in place, but can still slide quickly if you need to access something. I do wish the bag used something other than buttons to close shut, but it isn’t too hard to get it closed on the go.


Ultimately, I don’t think the Rough Rider leather messenger bag will let you down. Waterfield products last for quite a long time, so I don’t believe I will be buying another messenger bag for a while. Waterfield’s Rough Rider is one of the best messenger bags on the market.

Appletell Rating:

Buy the Rough Rider Leather Messenger

Provides: Laptop and tablet storage, transportation and protection of various items
Developer: WaterField Designs
Minimum Requirements: Laptop, tablet, other items
Price: $335 for 13″ laptops, $355 for 15″ laptops
Availability: Varies based on production run

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