As we have previously let on, we have an affinity for leather bags. They look cool and they can take a beating and continue looking stylish and professional. Our pick for the best everday carry leather messenger bag is the Saddleback Leather Medium Briefcase, in Chestnut. More specifically — the older model now only available second hand.
Owning one really is an experience. You don’t take the bag out as much as the bag takes you out. It enters a room ten degrees cooler and ten feet taller than everyone else. To date, a Saddleback Leather bag in Chestnut brown is the only thing to have ever received a heartfelt apology from Donald Trump.
Saddleback Leather rose to prominence owing to its high quality leather bags and its 100 year warranty. In the halcyon days of Saddleback they focused almost exclusively on bags. I so doing they maintained a level of quality that was unmatched. Unfortunately, as is so often the case, in recent years they have switched up their designs and expanded their offerings — apparently to the detriment of their bags.
Luckily there remains a healthy second hand market. My suspicion is that people shell out big bucks for a bag that they don’t realize will weigh more than most ultralight laptops (seriously, the medium briefcase comes in at just under 7 lbs!). However, if you know that going in, you can often score a decent deal on eBay or Etsy and get a lightly used bag with at least nine decades left on the warranty.
The key to finding an older, higher quality Saddleback Leather bag is to look at the logo — the older models had the company name written in script on the flap, just above the strap. Newer models have the new logo, a dog’s head, and have been reportedly more prone to issues with stitching and are generally found to be of lower quality. As always, make sure the item you bid on is being sold by a user with positive reviews and a good return policy.