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Rough Rider Messenger Bag
Rough Rider Messenger Bag
Strap close up
Strap close up
Sturdy, dual-layer leather handle
Sturdy, dual-layer leather handle
Industrial-strength snaps for easy access
Industrial-strength snaps for easy access
Leather pass-through slot for convenient carrying
Leather pass-through slot for convenient carrying
Full grain leather gets better with age
Full grain leather gets better with age
Front pocket
Front pocket
Rough Rider interior
Rough Rider interior
Stays compact even when fully loaded
Stays compact even when fully loaded
Stays compact even when fully loaded
Stays compact even when fully loaded
More customer reviews below
More customer reviews below
Black Leather Accent
Black Leather Accent
Blue Leather Accent
Blue Leather Accent
Crimson Leather Accent
Crimson Leather Accent
Espresso Leather Accent
Espresso Leather Accent
Gray Leather Accent
Gray Leather Accent
Grizzly Leather Accent
Grizzly Leather Accent

Rough Rider Messenger Bag

  • Video
  • Product Info
  • Specifications
  • What Fits
  • Press
  • Reviews
  • FAQs

Transport your digital world in the sturdy leather Rough Rider. A unique shoulder strap system keeps contents close and comfortable, the rugged leather develops a remarkable patina, and a padded laptop pocket keeps your tech protected.

All our products are crafted locally in our workshop by the most skilled sewing team in San Francisco.


  • Made from premium naturally-tanned distressed full-grain leather

  • Dimensions & Weight:

  • 16.5” (L) 11.5” (H) x 3.5” (W); 3.5 lbs.
  • Volume: 10.75 liters



    • The new interior houses a waxed canvas, plush, padded laptop compartment that readily fits up to a 15-inch MacBook Pro.
    • Two slots hold an Apple Pencil, Surface Pen or a few run-of-the-mill ballpoints.
    • A rolling suitcase handle pass-through facilitates hands-free carry from airport curbside to gate.
    • Six premium, full-grain leather accent choices under the panel add a pop of color.

    Classic Features
    • Constructed of thick, full-grain leather with raw edges, it exudes an adventurous yet sophisticated look and develops a beautiful patina with use.
    • A dual-layer leather flap shuts securely with strong snaps and is adjustable to two lengths, so users can fill the bag to capacity or cinch it tight. Either way the bag maintains its slim profile.
    • An unlined interior and natural edges reveal the leather’s premium quality.
    • A sumptuous leather panel under the flap creates a color splash and is available in six color choices.
    • The innovative strap system compresses bag contents to maintain a slim profile and positions the bag snugly against the body to help ease back fatigue.
    • Two deep, waxed canvas pockets in the main compartment fit an iPad, iPhone and additional necessities.
    • A full-width, luxuriously-soft, lined pocket under the flap stows additional electronics or personal items.
    • A floating shoulder pad with a no-slip underside keeps the shoulder strap in place.
    • A top leather handle allows for a quick grab.

    The Rough Rider padded laptop pocket fits devices up to 14.25" x 10", like:
    • 15" MacBook Pro with Touch Bar, Retina
    • 13" MacBook Pro with Touch Bar, Air Retina
    • iPad Pro 11”, 12.9” with Smart Keyboard Folio
    • Surface Book 3 (13.5" & 15")
    • Surface Pro X, Pro 7 with Type Cover
    • Surface Laptop 2
    • Pixel Slate
    • Dell XPS 13, 15
    • Lenovo X1 Carbon
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    This Is The Perfect Laptop Bag

    Forbes - December 13, 2015

    “And one really needs a messenger bag that strikes a balance between playful and professional. The Waterfield Rough Rider does just that.”

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    How I nearly became hooked on a $335 laptop bag

    Engadget - May 11, 2015

    “The Rough Rider is functional, wonderful to look at and built to last forever. It's the nicest bag I've ever had; I can say that without any hesitation.”

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    Laptop bag is a sturdy throwback

    The Dallas Morning News - July 5, 2014

    “Overall, this is a bag for someone who is more comfortable carrying a briefcase than a black canvas computer bag.”

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    Gear We Love: Rough Rider bag takes you through even the toughest commutes

    Macworld - June 2, 2014

    “Though the Rough Rider may not be the cheapest entry in the commuter's bag race, it's one of the nicest and most durable we've seen.”

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    Review: The Rough Rider Leather Messenger Bag by WaterField Designs

    AppAdvice - March 18, 2014

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

    Aesthetic Appeal: ★★★★★
    Wow Factor: ★★★★★
    Build Quality: ★★★★★
    Value: ★★★★☆

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    Review: Waterfield Rough Rider leather messenger bag (Verdict: Retro cool)

    ZDNet - March 10, 2014

    "I've been a backpack user for the past several years, but I may have found a reason to switch back to a messenger bag. This is one of the sweetest bags I've seen in a long time."

    Customer Reviews

    Based on 48 reviews
    A buy it for life bag

    Incredibly pleased with the bag and can't wait to use it for many years to come. The bag come with brand new stiff leather and I look forward to breaking it in and making it my own. The push button clasps are surprisingly easy to close due to the stiff leather and lining up well with the male clasps.

    Beautiful product

    Very happy with the communication from WaterField. My selection was out of stock but very quickly repopulated. Love the piece.

    Excellent and sturdy bag!

    I’ve been checking out the
    Rough Rider bag for a while but finally last month succumbed to purchasing one. It’s expensive but the build quality is incredibly good. I usually carry my 15” MacBook Pro in it with an assortment and accessories. And I carry my lunch in it as well. Did I mention the build quality? It’s absolutely recommended for anyone looking for a leather bag that can carry lots of stuff and still feel comfortable.

    Great bag!

    I've had my Rough Rider bag for a little over a month, and I already love it. I liked the look of it when I came across it online, but it's so much more impressive in the 'flesh.' The quality is exceptional, with plush interior pockets for laptops and tablets. The leather is very high quality, and the overall construction is terrific. I was looking for something distinctive, and this bag more than met that criterion. Some specific things to note... First, the bag is extremely well balanced. With all my prior messenger bags I've had to wear the shoulder strap across my body to keep the bag from sliding off my shoulder. This bag is really comfortable to wear on the shoulder, probably a combined effect of the way the strap is attached to the body of the bag and the excellent shoulder pad. Second, I had some air travel with the bag recently, and although I was expecting to have to lay it on its side under the seat in front of me, I found that the bag fits upright with the flap is open (which gave me access to its contents during flight). A pleasant, legroom-enhancing surprise! Third, I'd been concerned about the bag being smaller than bags I've had and overpacked in the past. But it held everything I needed to have with me during travel, and the two different snap placements meant that I had some room to fit some additional gear. Last, I wasn't completely sold on the snap closure, and at first I found it cumbersome, especially getting things out and back in again at the airport. But it hasn't taken me long to get the hang of the snaps.

    I'm looking forward to seeing how the bag breaks in, especially the change in the appearance of the leather over time, but I can happily see that this one will be with me for many years.

    Messenger Bag

    Very satisfied with my new Messenger Brief. The quality is better than expected. Very attractive looking too.

    Why use full grain leather?

    Full-grain leather has a super tight grain so it resists moisture very well, and it's strong and durable. We believe in making products of the highest quality—we never skimp on materials. Full-grain leather is ideal for handles; your fingers will feel the difference. Of course, leather lines the bottom to help the Rough Rider withstand various surfaces. The leather also develops a beautiful patina so it will add to the Rough Rider's character over time.

    Have a question about this product? Contact us at

    • Rough Rider Messenger best bag ever.
      - Brian C., Florida
    • Rough Rider arrived. Muzetto isn't lonely!
      - Cale C., Texas
    • Rough Rider love at first sight!
      - Fernando M., Maryland
    • Rough Rider. Form. Function. Indestructible. Me.
      - Sam H., Georgia