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

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

Summary: 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.

Review: Waterfield Rough Rider leather messenger bag (Verdict: Retro cool) - Jason O'Grady

An unfortunate side effect of the notebook computer revolution is that we new have to slog our computers hither and yon and often to and from our placers of work each day. Mobility, it seems, has a price. Our reliance on portable computers doesn't mean that we have to look like borgs when we carry our work-issued laptops home each evening. Computer bags are personal items that tell a lot about the people that carry them, and like one's clothing, they also make an impression when we arrive at a meeting or interview. 

If I'm going to carry a computer bag daily, I'd prefer it to be stylish and substantial rather than the company-issued black cordura bag that was purchased via some volume purchasing agreement. 

Enter the Rough Rider leather messenger bag from Waterfield Designs, Inc. ($335). It's a gorgeous shoulder bag made from high-quality leather and features natural edges and a vintage, broken-in look that makes it distinctive and unique. The leather has the patina of a baseball glove that you've used for ten years and it feels even better. 

Don't let the Rough Rider's gruff exterior fool you, it comes with four deep pockets for your gear. Two waxed canvas are inside the main compartment and another two are lined with soft material that won't scratch or scuff your iPad mini or iPhone. Dimensions are 15" x 10.5" x 3.5" and it weighs in at 2.9 pounds. The brown leather can be accented by trim in either black, copper, pine, green, flame or pearl.

Review: Waterfield Rough Rider leather messenger bag (Verdict: Retro cool) - Jason O'Grady

Since the cavernous interior is simply unfinished leather, you'll need a sleeve case for your laptop. Waterfield is the best-of-breed manufacturer in that category too, and I highly recommend that you go with their Outback sleeve ($59) to protect your MacBook Pro (they make them in sizes to fit most laptops). The vintage look of the waxed canvas is the perfect fit for the very well-worn Rough Rider bag. 

The snaps on the outside of the Rough Rider allow you to snap in closed in two different areas (depending on how much stuff you've crammed into the bag) and I would have preferred a big old buckle or some other vintage-looking clasp, but the snaps get the job done. Some will balk at paying $300+ for a bag, but when you consider what the materials cost and the fact that it's made in the U.S. (San Francisco, actually) it's not out of line. Quality doesn't come cheaply and Waterfield doesn't skip in materials department, so you get what you pay for. 

I'm typically a backpack guy (its the whole hands-free thing) but the Rough Rider and Outback sleeve combination are easily the most beautiful bag sleeve combination that I've seen in a long time. If you're looking for a high-quality and extremely good looking shoulder/messenger bag take a hard look at the Rough Rider, you won't be disappointed.

Review: Waterfield Rough Rider leather messenger bag (Verdict: Retro cool) - Jason O'Grady

Topic: Apple

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  • If it's an old bag you are looking for

    take my girlfriend, please....

    [drum roll and cymbal]

    Just kidding.....

    Nice retro bag!
  • Manbags

    Didn't Seinfeld cover this quite some time ago?
    • Exactly

      Nothing says retro-cool like A hipster manbag named after a gas station brand condom....
  • Pricey, isn't it?

    A few years ago I bought a bag in a similar style from Scaramanga in the UK. It is an incredible bag with a beautiful finish and top-notch stitching. It easily holds my MB Pro Retina with all the bits and baubles (charger, mouse, hard drive, etc.) and came in at about 1/3 the price.

    This whole 'Retro Cool' thing has just taken normal, everyday ho-hum leather products and priced them out of reach for all but the richest of hipsters.

    Order one from Scaramanga and get a truly beautiful piece of art that will patina and distinguish with age and not an over-priced, over-produced "made-to-look-like-dad's-old-Dingo-boots" bag from some fashion giant dipping their spoon into the hipster pie.
    • Yes......and They're Worth It

      "...over-priced, over-produced "made-to-look-like-dad's-old-Dingo-boots" bag from some fashion giant dipping their spoon into the hipster pie." could be made from a person who was a bike messenger in downtown San Francisco and puts an incredible amount of care, detail and design into bags that are hand made in small quantities, made to order with a ridiculous amount of options. And because they're hand made to your specs instead of mass produced, they cost more.

      They're not a fashion giant.

      They care about quality and design. As far as I can tell, they could care less about hipster pie.

      It's not a normal, everyday ho-hum leather product because of the care, effort and design that went into it.

      You might want to pay attention to what you slam next time.