This review is for the medium classic briefcase in chestnut, which I received as a gift recently.  I had been eyeballing the Saddleback briefcase for 2 or 3 years so I have done a lot of thinking, comparison shopping, reading of reviews, and examining them first hand when I saw one out and about. Also, as I mention in another comment here, I am a leather craftsman (belts and holsters mostly) so I know a thing or two about leather - indeed, I'm a bit obsessed with it.

The Saddleback is replacing a soft-side leather briefcase made by Samsonite that I bought in 1993. It has served me well, but is a bit on the small side for my needs and is suffering from the very problems that the Saddleback company is trying to avoid: cheap components and construction that make the bag wear out before it should.  The Samsonite I have used cost me $100 and was made with some nice soft leather.  The leather has held up wonderfully over the years especially since I treated it every year or so with some Lexol conditioner.  The shoulder strap was the first part to go.  It was made with two pieces of leather strap that met in the middle and was sewn onto the shoulder pad.  Seams are the Achilles heel for a leather product and this was the fatal flaw for the strap. Because the shoulder strap wasn't a single piece all the way from end-to-end, it began the seams began to pull apart after a few years.  Then the backing on the shoulder pad began to crack and come apart. It was then I confirmed what I had suspected and lamented; the bag was made of nice leather, but the trim was made with inferior vinyl. Your leather product is only as good as the weakest materials in it, so why would a company make a very nice leather bag with cheap and far less durable vinyl?  I made a replacement strap and it has held up just fine. Next, the trim along the seams began to crack and fail. It was also vinyl. The lining started to go next, as it was a cotton fabric. The hardware has held up reasonably well, but was obviously on the way to failure.

I give this description to point out the benefit of the Saddleback briefcase. It has heavy-duty hardware, is made with nothing but leather, and all the stress points are reinforced.  If my $100 Samsonite has lasted me almost 20 years, certainly the Saddleback will last me a lifetime.  The seams are stitched with heavy thread, double and triple stitched at major stress points, rivets are added, and many areas subject to stretching have a synthetic nylon strip sewn in to help keep the leather from stretching too much.  The fasteners are simple buckles with no springs to break or wear out.  It's a rugged bag made for heavy use. If you are just looking for a bag to lug around heavy items (I'm a college professor and I regularly carry around my laptop and many books), this will do it. If you plan to use it for carrying a folder or two back and forth to the office, this may not be the best bag for you. Rather, you may want to consider the thin briefcase made by Saddleback or one of their satchels.  This bag can be converted into a backpack, and although it's unlikely I will use this feature, it's a nice option to have just in case.

Lets talk about the biggest complaint I've read here and elsewhere: it's heavy.  Yes, it's a bit on the heavy side.  It's a big briefcase made of thick full-grain cowhide leather with a smooth pigskin lining and heavy-duty hardware.  That's heavy stuff.  I don't particularly mind it because I am used to carrying a heavy briefcase. However, if you are accustomed to carrying a nylon bag or thin leather bag, this will be quite an adjustment for you.

Next complaint I commonly see is that it's stiff.  Yes, it's a bit stiff when new.  High-quality full-grain leather is stiff when it's new.  This is not garment leather like on a leather jacket or a sofa.  For those familiar with the process of breaking in a new baseball glove or shoes, this bag is no different.  It's much more rigid when new, but with time and use, it will soften and loosen up.  It takes time, which for me is part of the allure of a nice leather bag. I love the experience of watching it break-in over time.

As far as size goes, I think the large bag is probably the best choice for most people. I received the medium bag and it's almost too small for me.  I carry a 13" MacBook Pro in a neoprene sleeve and it's a tight fit into the bag from side to side. This may be related to the bag being new and will ease up as the bag breaks in a bit.  It's not so tight that it's going to damage the computer, but it's a little more snug than I am used to (kind of like trying on new shoes after wearing your trustee broken in pair).  If you have an average size laptop, it is very unlikely you will be able to fit it into a medium bag.  Front-to-back there is plenty of room in the bag for my laptop, cords, accessories, books, papers, etc.  If you need a little extra space for small items, you may want to consider the pouch Saddleback makes and the owner clips onto the front of his briefcase.  Being a leather worker, I made myself a shameless copy of their pouch (pouches are much easier to make than fancy briefcases) and I use it to carry my keys, my phone, a pocket knife, pens, etc.  I also regularly slip my iPad into the pocket on the back (in a leather sleeve I made for it) and it works fine.  I considered trading my medium in for a large, but when it came time to box it up and send it back, I just couldn't do it since it was a gift from my wife and I am sentimental like that.

And that brings me to my next point, which is Saddleback's customer service.  I found them to be extremely friendly and efficient.  The company is based in Texas, but as of the time of this writing, they have employees all over the US who work remotely. I tell this to demonstrate how well they can deal with customer issues.  Over the course of a few days, I communicate with 4 different people in 4 different states, but my emails were answered quickly and each person appeared to be up-to-speed on the previous communications.  I had contacted Saddleback a few times in the past to ask questions about their products and I was always answered quickly with no pressure to buy their products.  The company claims to have a 100 year warranty, and from experiences I have read on the Internet (surely they are all true because you can't put anything on the web that isn't true), they do stand behind their products when there is a problem. As far as a return policy, it appears that for warranty issues, they cover the shipping costs. If you want to do an exchange as in my case, all shipping costs are yours.  They will issue a return authorization, and all returns must be in as-new condition.  They will then credit you for the cost of the return and you place an order for a new item.

Another question I have seen on these bags is about where they are made. My investigation has led me to think that the bags are made in Mexico and are not hand-crafted one at a time by the company's owner.  Take that info for whatever it's worth.  It's a big deal for some, not so much for others.  Although I'd have preferred it to be 100% made in the USA, it's still an American-owned small business with American employees. Also, Mexican leather is known to be some of the better quality stuff on the market.  The quality of the leather and craftsmanship appears to be good. The bag looks to be machine stitched with a lock-stitch machine which is typical and relatively durable. Saddle-stitching is better, but can only be accomplished by hand and is very time consuming (and would increase the cost of the bag substantially).

Now, cost.  As a guy who knows leather and works in leather, do I think the cost is justified?  In this case, yes.  I contemplated just making a bag for myself, but upon inspecting one of these first-hand, I knew how much work it would require.  I knew that I didn't have the patience or the experience with this type of work to pull off a finished product like this.  For a small guy like me, I suspect the materials would run me somewhere in the range of $100 - $150 and the time to make it would be several hours.  Quality stuff isn't cheap and such is the case with the Saddleback bag.

Finally, I'll speak to the style of the bag. This is not a metropolitan or high-fashion sort of bag. It's a rugged looking, earthy, business casual bag. If you wear khaki pants or jeans to work, this is likely to be your style.  If you wear finely tailored suits and wingtip shoes, the classic briefcase may not be your style (but the thin briefcase may be). In the short time I've owned it, I have gotten several compliments on the look and the smell; the smell of the leather is wonderful. I picture myself as Pigpen on Peanuts, but instead of a cloud of dust following me around, I'm cloaked in the smell of leather. :-)

Overall, I'm very pleased with my Saddleback briefcase. Also, if you haven't taken a look at the company's website, it's a great resource for Saddleback products that includes high-def video descriptions of most items.

UPDATE -- OCTOBER 2015

I've owned this bag for a couple of years now and it has served me well.  One problem I did have is with the hardware that attaches the shoulder strap to the bag.  Mine came with some clasps that had a screw ring and a pivot joint, not the trigger clasps shown in the picture.  The clasp would pivot open and hook on the side of the bag, then you push it closed and screw the ring up to keep it secured.  Well, mine was defective and every so often the thing would pop open and the bag would fall to the ground.  I called Saddleback to get a replacement, but they told me I had to send the defective strap back to them before they would send a replacement.  This means I would have to go without a shoulder strap for an unknown period of time before I got a replacement sent to me.  I thought that was pretty crummy customer service considering the cost of the bag and how much hype they put into their warranty.  Ultimately I said to heck with it, cut the old parts off and replaced them myself using copper rivets and some different trigger style clasps that can't unhook like the originals.  I have downgraded my rating from 5 stars to 4 stars for this reason.