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Review: Rough Rider Leather Messenger Bag

Rough Rider Messenger

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Rough Rider Messenger

If Indiana Jones owned a laptop, this is the bag he’d carry it in. Try not to drool.

Waterfield Designs, leather accessory crafters extraordinaire, have taken the wraps off their greatest creation yet: the Rough Rider Messenger Bag. And you want it more than you know.

The Rough Rider is a high-end messenger for toting your laptop, iPad, important papers, digital camera, and whatever else you need to carry. Handmade using a thick, ultra-rugged leather, “durable” is not a strong enough word to describe just how sturdy this thing is. Waterfield actually packages it with a note explaining that its distressed leather is fresh, so it’ll feel stiff at first but will soften over time much like a leather jacket. An intriguing design decision juxtaposes rough leather edges with smooth, clean lines across the entire bag.

Rough Rider Messenger top handle
Rough Rider Messenger top handle

All that thick leather makes the bag heavier than you’d expect from a messenger, but this is no ordinary bag. The added heft makes it feel more like a hard metal briefcase, lending it’s owner a pretty profound sense of confidence. Having carried it around for a few weeks, I can assure you that the Rough Rider turns heads.

The roomy interior is big enough to hold plenty of contents. The main compartment is surprisingly huge, though oversize laptops won’t fit. My 15″ MacBook Pro fits just right, with its edges touching the sides of the bag. There’s tons of space left over for more of my belongings.

Rough Rider interior
Rough Rider Messenger interior

Waterfield has come up with an inventive strap that’s connected to the bag in a way unlike anything I’ve ever seen. Take a look at the photos to see the details, but basically it extends upward from the bag at a slight angle instead of straight up. This unique attachment helps to keep the bag snug against your body instead of dangling free. The size of the strap is a good example of how every detail of the Rough Rider has been designed for maximum durability. It’s a good 2″ wide and it’s not detachable (though the shoulder pad is removable), so you can count on it to be unfailingly strong. There’s a nice, sturdy handle atop the bag as well.

Rough Rider Messenger shoulder strap
Rough Rider Messenger shoulder strap

Under the front flap, there are a pair of snaps on each side, giving you two options for where to close it based on how much the messenger is holding. Like everything else, these snaps are high-end; once you’ve snapped them together, there’s no way they’re popping open by accident.

Inside below the flap are a pair of nylon canvas pockets that come in your color of choice. (No bright colors here; these are muted colors selected to suit the messenger’s serious, professional sensibility.) Opposite the canvas pockets — inside the main compartment — are two more matching pockets of the same size.

Rough Rider Messenger pockets
Rough Rider Messenger pockets

Therein lies my only complaint about the Rough Rider: I wish there were a few more pockets, and that they were more varied in size. The four pockets it has are great, made of nylon or deliciously soft leather — and they won’t scratch your digital devices. But they’re all the same size, a width that’s a little too big for your wallet or phone, but not wide enough for your iPad (Waterfield says they will hold an iPad Mini). I found myself wishing for a few smaller pockets to hold your phone more snugly, or some narrow slots for pen or stylus. Also, all four pockets are inside the messenger. Outside pockets are kinda nice for holding items that you need at-the-ready, like a boarding pass. It’s a small gripe; you won’t have any trouble getting any of those things inside the Rough Rider, they just might move around a bit more than you expect.

The Rough Rider Messenger is a gorgeous, high-end, super-strong bag that will hold just about anything you want to carry while withstanding whatever’s thrown at it. It makes a very bold statement, and it’s guaranteed to cause envy in everyone you meet. Best of all, unlike most things in life, it actually gets better with age.

Picture of Kokou Adzo

Kokou Adzo

Kokou Adzo is a stalwart in the tech journalism community, has been chronicling the ever-evolving world of Apple products and innovations for over a decade. As a Senior Author at Apple Gazette, Kokou combines a deep passion for technology with an innate ability to translate complex tech jargon into relatable insights for everyday users.

One thought on “Review: Rough Rider Leather Messenger Bag

  1. I love all the heavy/worn leather, but there’s something about the strap that doesn’t sit right with me. The whole thing does look good, but $335??? I wish I could afford one of them!

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