Enjoy Father's Day
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

Adventure awaits. Transport your digital world in the sturdy Rough Rider. A unique shoulder strap system keeps the contents snug and riding close to your body, and the clean professional look exudes an "already been around the world a couple of times" confidence. The rugged leather develops a remarkable patina that — like a good saddle — only gets better with age. The unlined interior and clean, natural edges highlight the character of the bags's quality leather. Inside is a padded laptop compartment and pockets for tech gear. The leather flap snaps securely shut with two options to adjust the fit based on the bag's contents. 

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 2 (13.5" & 15")
    • Surface Pro 6 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 43 reviews
    Nice bag

    Extremely well made and just enough pockets for a slim, functional look. You can fit a 17 inch laptop in the main cavity in a pinch or smaller ones in the padded sleeve.

    This is a Beautiful, Stylish, Rugged, and Downright Awesome Bag!!

    I was looking for an upgrade to my laptop bag and once I laid eyes on the Rough Rider I had to have it. This is a well made and stylish bag. The stitching is beautiful. The strap feels strong and secure. The handle on the top is a nice touch and make picking up the bag simple and convenient. All of my gear fits inside great. I chose the black color and also purchased the matching City Slicker for the NN3DS XL. To top it all, the best part of this bag was the smell of leather as I opened the package. I will be a customer for life.

    Get More than what you pay for

    If you look at my account, you’ll notice that I’ve been heavy Waterfield Addict for the last 15 years. It all started after reading a review about the Cargo bag which was my first purchase back then…..it was followed by another large Cargo, Muzetto, Bolt Brief Case, Staad Attachee, Maverick, the first version of the Rough Rider, an Air Porter along with numerous wallets, sleeves and gear cases….and I was never disappointed.
    I never understood why you actually discontinued the Rough Rider a while back and was more than happy to now see the new version of this gorgeous bag. Sure – the price isn’t cheap, but in this case, you get more than what you pay for. The bag just is a piece of beauty with the thick, distressed leather and craftsmanship that nowadays is hard to find. I really like the padded laptop compartment that makes any sleeve for my macbook unnecessary. This will be my go-to bag to take to work and on business trips from now on and I’m sure it’ll probably outlast my working life. So far, I never managed to destroy any of your bags, and I’m sure the Rough Rider won’t be the first.
    Thanks a lot! And keep up this great work.
    5+ Stars for this one!

    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 HeyGary@SFBags.com.

    • 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