Rough Rider Messenger Bag

  • Green
  • Rough Rider Laptop messenger bag
    Rough Rider Laptop messenger bag
  • Main compartment (sleeve not included)
    Main compartment (sleeve not included)
  • Rough Rider under flap
    Rough Rider under flap
  • Rough Rider shoulder strap
    Rough Rider shoulder strap
  • Rough Rider handle
    Rough Rider handle
  • Flame
  • Black
  • Copper
  • Pine
$335 $335 $335 $335 $335 $355 $355 $355 $355 $355 The Rough Rider leather messenger bag stays slim-looking even when full. Can carry laptops, MacBook, iPad, tablets and other stuff. For business and pleasure.
Buy it now from $335

Choose Options


Most colors in-stock.
Email for availability.

  • Watch Videos
  • Product Info
  • Color Variations
  • Testimonials
  • Reviews

Adventure awaits. The Rough Rider is made for today's urban wrangler, transporting digital devices and documents in sturdy, long-lasting leather. A unique shoulder strap system keeps the contents snug and riding close to your body, and the clean professional look exudes a "already been around the world a couple of times" masculine confidence. The rugged leather develops a remarkable patina that—like a good saddle—only gets better with age. The un-lined interior and clean, natural edges highlight the character of the bags's quality leather. Four deep pockets keep gear in place: two waxed canvas inside the main compartment and another two lined with soft, scratch-free material under the flap that are perfect for stowing an iPad mini and smartphone. The leather flap snaps securely shut with two options to adjust the fit based on the bag's contents.

With the Rough Rider slung neatly over your shoulder, you're ready to ward off anything from horse thieves to hostile takeovers.


  • Made from premium naturally-tanned distressed leather
  • Size and dimensions:
    • 13" Rough Rider, 15" x 10.5" x 3.5", 2.9 lbs.
    • 15" Rough Rider, 16.5" x 11.5" x 3.5", 3.5 lbs.
  • Trim colors: black, copper, pine, green, flame
  • Insert laptops, MacBook, iPad, tablets, e-readers, smartphones, iPhones, or other digital gear











Hi Gary, got my Rough Rider delivered in time, even with the snow storm that hit us on Monday.

I am already using it and totally love it. Fits my MBA + iPad (inside one of your sleeves, my phone wallet, chargers/cables, papers, sunglasses and more stuff.

I am already thinking of what a RR would look like with either a back pocket, a front pocket, or both. If you get around designing a RR2, let me know. In the meantime, I'll enjoy the hell out of this one!

Take care, thanks for your quick and courteous service.



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.”


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.”

The Dallas Morning News

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.”


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.”

Rating: 4/5 mice

Review: The Rough Rider Leather Messenger Bag by WaterField Designs

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: ★★★★☆

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

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."

Waterfield Designs Rough Rider leather messenger review

Waterfield Designs Rough Rider leather messenger review

TechnologyTell - March 7, 2014

"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."


Have a question about this product? Contact us at

Other items to consider