Rough Rider Leather Messenger

The Rough Rider by WaterField Designs Choice of Six Accent Colors Rough Rider Interior Compartment and Two Pockets What Fits in the Rough Rider (Laptop SleeveCase, iPad Smart Case, and Finn Wallet not included) Rough Rider Shoulder Strap & Side View Rough Rider Handle Rough Rider Flap & Snap Closeup
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The Rough Rider. $335

Order now for April 30th Production Run
April 15th Production Run Sold Out)

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
  • One size: 15" x 10.5" x 3.5" / 2.9 lb.
  • Trim colors: black, copper, pine, green, flame, pearl
  • Insert laptops, MacBook, iPad, tablets, e-readers, smartphones, iPhones, or other digital gear
Accent Colors
Rough Rider with Black Accent
Black Accent
Rough Rider with Copper Accent
Copper Accent
Rough Rider with Flame Accent
Flame Accent
Rough Rider with Green Accent
Green Accent
Rough Rider with Pearl Accent
Pearl Accent
Rough Rider with Pine Accent
Pine Accent

From: Fernando
Subject: Re: Your SF Bags order

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, by phone wallet, chargers/cables, papers, sunglasses and more stuff.

I am already thinking of what a RR would look like with wither 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.


Waterfield Designs Rough Rider leather messenger bag: Review

“The Rough Rider might not be inexpensive (that's my only beef with the bag), but it is going to outlast a lifetime's worth of Apple laptops and accessories while looking better with age.”

Rating: 3-1/2 stars (out of 4 stars possible)
TUAW Rating of 3-1/2 stars (out of 4 stars possible)

Review: The Rough Rider Leather Messenger Bag By WaterField Designs

“How Does it Stack Up? 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)

“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

“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.”

AppleTell Rating: 5/5

Suggested Cases & Pouches for the Rough Rider

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