Saddleback Leather Messenger Bag Review & Accessory Giveaway

I’m really rough on computer bags. It sucks, because I end up going through really nice backpacks way too often. I was using a Wenger backpack that my wife and I affectionally refer to as the “bag of holding” because it has a seemingly endless capacity. It was essentially new when my friend gave it to me…and now, the straps are coming apart. Probably because I do things like this.

I just kind of accepted this as life, you know? Bags are temporary, and you should just sort of be looking for the next one all the time. Or so I thought.

I don’t know how I first heard about Saddleback Leather…I suspect it was a link from Reddit. But I checked them out, and I really don’t think I believed much of what I read. It just sounded too good to be true. The story of Blue, the 100 year warranty, and the multiple compliments a day. But the bags DID look good, so I tried to learn more about them.

People on Reddit rave about them. The reviews on Amazon for the bag I wanted were almost completely positive. And aside from that guy, I’d never heard anyone say anything against them at all. Plus, it wouldn’t look out of place in an Indiana Jones movie.

My wife and I talked it over. And when I say “talked it over”, I mean she said no. And to be honest, I understand. The messenger bag that I wanted was $400. That’s a huge amount of money for a bag. But like I said, I go through bags pretty frequently, and to me, it makes financial sense. Pay big once for something that will last instead of always be shopping for another bag. If the bag lasted even 10 years, I’d probably break even. Eventually, she counted it as my birthday present and a bribe. I counted it as a win. :-D

So I ordered the messenger bag. And waited. When you have something you want, delivery takes twice as long, so I bided my time by watching YouTube fan videos. It should say something that this is the kind of bag that has fan videos.

I got the bag, and the first thing I thought was, “oh wow, I’ve never felt leather like this”. And seriously, I haven’t. I have apparently never dealt with full grain boot leather, because it doesn’t feel like any of the leather I’ve had before. I’ve had leather shoes, jackets, belts, wallets, whatever, but none of it felt like this. It’s crazy-thick. And…I mean, it doesn’t even feel like what I thought leather felt like. But the smell is amazing, and it looks even better in person than it does on the website.

I’ve had it for a couple of months so far, and I feel comfortable in reviewing it. I took it with me to LISA12, so if you saw me there carrying a swag looking leather computer bag, that was this one.

So what do I actually think of it?

Well, first, the quality is totally there. You won’t find snaps or zippers, because those break. It’s all leather straps and buckles. Anything that looks like a snap is actually a rivet. I have NO torn or frayed threads (and I promise, with most other bags by now, I would). There’s no ripped leather, no seams coming apart, and nothing that I could possibly ding on quality.

As you look at the pictures I took, you’ll see plenty of scuffs. That’s not a quality ding. That’s character in the making, I promise. This bag is already much, much more supple than it was when I got it, and it looks like I use it because I do. It’s barely 2 months old, and it’s been shoved under plane seats and overhead bins, in trunks, it’s been knocked over dragged here and there. It’s building into the kind of bag that makes you go, “wow, that’s awesome”. And the thing about the compliments is right. I’ve had at least a dozen people compliment me, including the TSA folks.

That being said, this particular bag is not the perfect computer bag. Inside, there are only two small pockets on the ends. There’s a removable leather divider that can separate goods, but only imperfectly. On the outside, there are the two end leather pockets (which will fit a 20oz drink) and a back sleeve type pocket for papers or magazines.

As you can see, my 13 inch Macbook Pro fits in lengthwise (or standing), but it is a little tight lengthwise for now. After the leather stretches, it will fit more comfortably. Anything larger wouldn’t fit – I’m certain of that. I can actually keep a lot of stuff in my bag, though. As you can see above, I got a computer in there, plus at least one tablet, plus a notepad, and at LISA, I kept my SLR in there at times, too. It seems to be relatively rain-proof, since when it’s closed, there’s a decent amount of overhang on the side of the flap. I don’t think I would trust my computer’s life with this, but it’s “resistant”, I would say. You don’t have to worry about water permeating the leather, though.

It turns into a backpack by taking the straps off where they connect right now (at the top) and connecting them to the forged (yes, there is no gap, the rings are solid) D-rings on the bottom, and running it through a forged O-ring at the top in the middle. It functions pretty well as a backpack, but it takes a while to do the transformation, so it’s not something that you’ll want to do a lot.

On the other hand, this is the best bag I’ve ever had for running over my shoulder and across my chest. I’m a pretty big dude, and this has an insanely long strap. The bag sits comfortably on my hip with the strap running across my chest, and there’s at least another foot I could drop it if I needed to. My camera has a strap that’s too short to comfortably do that to. I’m SO glad this bag has the leather strap the size it does. If you’ve ever had a bag that with a strap too short to wear comfortably across your chest, you won’t have that problem with this one.

Also, it’s heavy. I don’t mind, because I’m pretty large, and it’s a small percentage of my mass, but it’s probably a larger percentage for you. Basically, the bag is 5lbs (2.25kg) empty. That’s heavier than a lot of people want to carry, and understandably so, but you should know what you’re getting into.

There also isn’t any padding, so you can’t throw a laptop around and expect it to be good. Even if you have an SSD, the LCD could break or get knocked loose, so be easy with your computer in it. On the other hand, when I’m not carrying my computer in it, I fear nothing. It’s amazing to have just bought this really great thing that I literally don’t have to worry the least bit about getting hurt. You don’t have to treat this with kid gloves at all, because you couldn’t possibly hurt it on accident.

So, would I recommend buying this bag? Probably, depending on who you are and how comfortable you are carrying a big bag that’s relatively heavy. I think you should also consider how you want to be able to treat the bag with your computer in it. This bag is going to outlive your computer, but you don’t want it to hasten your machine’s demise.

The slogan on the website is, “They’ll fight over it when you’re dead”, and I thought it was just a cute phrase until I got my hands on this.

So then the story gets weird. Because this is the kind of bag inspires people to make fan videos, they’ve got a Facebook page where you can interact with the company and hear about what’s going on. So of course, I friended them.

Fast forward a month or so, and one of their updates mentioned a contest. It was basically a “Share the link and whoever gets the most clicks will win a World Traveler gift set”. I normally eschew things like that because I don’t look at my friends as things to be sold. I do think it’s different when you actually care about the company and their products, though. It’s not like I was trying to sell out my friends – I really did like my bag and thought that they had a great product. In the end, I shared the link on my twitter account which gets auto-forwarded to Facebook, and I got a bit over a hundred clicks from doing that. (So if you were one of them, THANK YOU!)

The contest was four weeks long, with one prize set given per week to whoever had the most clicks. The first week, I was excited, because I thought I had a chance. Heck, I even hand made the ad which is running on the blog right now, over on the right (if you don’t see it, that’s because it only loads once out of every 4 pageviews) and linked it to my contest URL. At the end of the week, they announced that the winner was some guy who had been bragging in the original thread about buying 60,000 clicks so I promptly forgot about the contest since I had no chance.

Forgetting about the contest was primarily the source of my great surprise when I got an email from one of the folks at Saddleback that told me I had won the third week’s contest! Holy Cow!

So yeah…my prize came on Friday. I don’t really know what to say. Here’s what it looks like sitting in my living room:

wow. Just wow.

So…I have multiple thoughts. First, thank you to everyone who clicked on the ad or the link. I’m very grateful, and even moreso than I could before, I can completely assure you that if you’re looking at Saddleback and wondering if the quality is as high as everyone says it is, it really, really is. I’ve got almost $4,000 worth of their products in my house right now, and I feel pretty solid in telling you that every single piece of this is made at least as well as my messenger bag is.

Second, I can’t use all of this stuff. Now, my wife has expressly forbade me from giving away any of the bags…but accessories? I really don’t need all of the accessories. So here’s what I’m thinking…

Why don’t I give away some stuff? Maybe to the people who helped me win it? Maybe to you? Here’s what I’m giving away:

That is:

  • 5 leather keychain fobs, one in each color they make
  • 1 leather cup holder to keep hot coffee from burning your hand
  • 1 bottle of car Leather Care
  • 1 bottle of furniture Leather Care
  • 1 ID wallet (the other side of the wallet has a window for your ID)
  • 1 iPad 2/3 case

As for the value, the keychains are, as far as I can tell, priceless, as you can’t actually buy them. They come with the bags, but I don’t have five sets of keys. In fact, I don’t think I have five keys. And my wife already took the one she liked. So I’m giving the rest away.

The leather cup holder is the same way. You literally can not buy it. One sold on Ebay years ago for $53. For a cup holder (though please don’t sell these prizes. They’re nice, and you should keep and use them).

You can get the leather ID wallet for $33, the Leather Milk goes for $18 a bottle, but the big prize is the $111 iPad 2/3 case.

The only thing is that I don’t know HOW I should give it away. I like doing surveys for contests, because then it’s a trade. I get useful information and you get something that you like. But I’m not sure. So to start out, help me out by commenting and letting me know what you think a good topic for the survey would be. I want to keep it system-administration related (since this is, after all, a blog about system administration), but other than that, let me know what a good topic would be for the survey.

If I pick your idea, I’ll give you the first prize – one of the keychains.

  • Steven

    There’s really only one way to do this so that you know the winner actually deserves these manly prizes…cage match with rabid wolves. If they make it out, then they get their choice of prize.

  • With the renewed interest in ops education, perhaps something along that lines. Questions include “What would be a reason for you to pursue a degree in syadmin?”

  • Fred Woodbridge

    How many of you were born in November? ;)

  • Maybe a survey about what configuration management system people are using? And what source control they’re using to manage it (though I’ll be surprised if it isn’t overwhelmingly git), or what workflow they use for managing configuration management?

  • Give them to the first three people that responded today ;-)

  • LOL I guess it took me a while to respond today

  • Zed

    how about some more discussions on automation, especially in WAN environments

    ie. I’m in Australia, but most of the work I do (via ssh) is in Virginia, USA. For security, we have to connect via a bastion / jump server.

  • gizmomathboy

    Damn, Matt, the bag itself is sweet. Getting those prizes are just amazing.

    I’m impatiently awaiting the arrival of my expensive backpack. A Pelican U100. I was able to score it for $200 vs. the usual $300.

    Well, to mirror the longevity of your bag, how about ways sysadmins are creating processes and tools that can outlive them?

    Continual improvement should get us out of boring parts of our job, freeing us for more difficult parts, and increase the bus factor of the group

  • I see you make your own luck. Well done!

  • DTK

    If it were me, I would ask two questions in the survey along the lines of: “what is the coolest systems administration achievement you have had in the last couple of years?” and “what one resource should I be checking out to becoming a better systems administrator?”. -DTK

  • DTK

    Also, congrats on winning their contest; that is an impressive haul.

  • Ken

    I found this bag walking around in berlin in 2008. Its called It has interchangeable front flaps which pretty much changes the entire appearance of the bag.
    It is extremely durable and I used to go through bags a lot like you did. I also thought it was pretty expensive at around $200. But its going strong in 2013. :D

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