A Quick Look at the $400 WaterField Executive Leather Messenger Bag

The Executive Leather Messenger from WaterField Designs is a handcrafted bag that absolutely reeks of quality and elegance. It has a timeless design, dozens of thoughtful touches, and beautiful leather construction. And at $400, it’s also quite expensive.

I’m a pretty simple guy. I’ve been using modest laptop bags from the likes of Timbuk2 and Osprey for years. Bags around the $100-150 price range—expensive by some standards, but a pretty solid midrange when you look at the big picture. I’ve never been sold on the idea of a really expensive bag. What could one offer that I wasn’t already getting?

So when I got a chance to review the $400 Executive Leather Messenger from WaterField designs, I decided why the hell not. I’m not sure I can legally use this bag because I’m not an executive, but damn the man—it’s time to see what four Benjamins stacked on top of each other will get me in a laptop bag. This post is my first impressions of that bag. I’m keeping it as a long-term loaner so I can do an update in 3-6 months to see that sweet, sweet patina (and also how the bag is holding up).

So yeah, my first impression? Damn. This bag is a looker. It’s so classy, I honestly wondered how it would look next to my normal everyday wear. I’m not a “wear suit pants and a blazer every day” kind of guy—I’m more of a “t-shirt and camo shorts every day” guy. That’s kind of the opposite of the executive aesthetic, but I also don’t really care about any of that and use what I like, so that pretty much settled any worries I had. This bag is hot.

But what I’m generally concerned with when it comes to bags—especially messenger-style bags—is organization. The Executive Leather Messenger comes in two sizes: Compact and Full (you can see a size comparison on WaterField’s site). Since I plan on using this bag pretty exclusively for months, I opted for the full size, and I’m glad I did. I don’t usually carry a ton of stuff with me on the daily, and the full size leaves some room if I need to put anything extra in there. I’m not sure the compact would have.

The inside is roomy and has just the right amount of organization. A large, super-soft padded section is for a laptop, and a smaller section for a tablet has the same soft lining. The bigger area is wide open, but there are two smaller pockets available—one with a zipper, one without. Two additional soft-lined pockets are on the outside of the main compartment (just under the flap), which are great for your phone … or just sticking your hands in because, man, that soft liner is awesome.

I think what I’m most impressed with so far, though, is the construction. This bag is so solid—the leather is heavy and thick, and the stitching is great. It feels very well put together and durable. The clasp that holds the flap closed is also awesome—it’s a paragliding-style buckle that’s very satisfying to click shut and also stupid-easy to open with one hand. It’s metal, so you’re not going to break it easily. It should stand the test of time.

And I mean, for $400, I would hope so, but you never know with premium products. So far—and keep in mind I’ve only had it for like a week—it feels solid. I’ll let you know in six months how it holds up. I can’t say for sure whether or not it’s worth $400 just yet, but I can definitely tell you it’s a damn fine bag that I’m looking forward to using. Damn. Fine.