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

Rough Rider Messenger Bag

-257 in stock

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.

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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:

  • Rough Rider Messenger Bag:
  • 16.5” (l) x 3.5” (w) x 11.5” (h); 3.5 lbs.
    41.91 (l) x 8.89 (w) x 29.21 (h) cm; 1.58 kg
    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.

    • Domestic: Flat rate 2-day shipping. Details.
    • International: 2-3 business day delivery. Country duty/tax calculated at Checkout. Details.

    Customer Reviews

    Based on 51 reviews
    Perfect size and great quality

    Love the new bag. It is a perfect fit for my new MacBook Pro 16. Tablet pocket doesn’t fit my 12” iPad, too bad, but it fits inside when needed. Only wish is for a pouch as the space inside is pretty big and unstructured, no good place built in to hold power cords. Best part, the shoulder strap stays put when carrying on one shoulder without having to wrap the bag around my body. Wish it had the cool binder clip but the snaps are just fine. Great work!

    Excellent bag

    For perspective, I bought this bag to replace an aging Ona messenger, which can double for carrying both a laptop and a camera with a couple of lenses. This time around I wanted something more work focused as I ended up transitioning to a backpack when I wanted to carry both a computer and camera. The bag looks fantastic and seems built to last a long time with thick leather. I went with the blue accent and I think it adds a nice touch. Although I don't need a particularly professional looking bag for work, this could look the part in that situation.

    From a practicality standpoint, my two computers are a Surface Book 2 and a Surface Pro. I mostly carry the Book around with me these days, and this bag holds it without any difficulty. The sleeve is very well padded and lined, essentially like they built one of their laptop sleeves into the bag. I do wish the bag was a bit wider from front to back so I could carry my lunch in it as well, but the Surface Book with its gap hinge takes up a fair bit of space. I suspect people with ultrabooks or Macs would not have this issue as one review commented they were able to carry their lunch with them. I was worried I would hate the snaps on the front of the bag, and while I'd still prefer magnetic ones, I found I got used to them very quickly. The two pen slots are convenient for keeping the Surface Pen and a regular pen on me, while two other organization pockets are handy for other gear like a portable mouse and display connector. The bag obviously isn't cheap, but I expect I'll be able to use it for years.

    Very attractiv and well-made bag with two functional drawbacks

    First, this bag is really gorgeous in person and I can't wait to see how it ages over time. The interior is lovely. I love the fabric padding on the laptop and front tablet pouch. It makes it very easy to get a laptop in and out. It has a very slim profile that looks fantastic against your body. There are two things I wish were improved, however. The first is the use of snaps in the flap. I'm predisposed to just leaving the flap open for speed and convenience. Finding a snap is just annoying in general. You can throw it over the shoulder with the flap open no problem, but the you can't carry it using the handle that way. It's a minor complaint, but it may be important to you. The other issue is the strap. It's not a bad strap. The cover is terrific and provides a lot of grip to keep it on your shoulder, but I would prefer some attach points that can rotate so the strap can be straightened out more easily. Again, minor, but something I find a bit annoying on a high end bag.

    BTW, big shout out to the Waterfield folks. When I ordered the bag, they sent me an e-mail the next day that said they actually didn't have any in stock and needed to make one up. They claimed that would take five days, but I had the bag in hand in three days. Fantastic communication and customer service.

    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.

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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."


    The Rough Rider padded laptop pocket fits devices up to 14.25" x 10", like:
    • 16" MacBook Pro
    • 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


    The secret to the clean, svelte look is a tapered body and an integrated, flexible strap system. But that's not why the Rough Rider is a customer favorite. 


    "I love the quality of the leather and that it has the 'been-around-the-world' look while still being stylish. I have already gotten several compliments on it!" - Kevin M. 

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