Waterfield’s leather messenger bag gives my gadgets the treatment they deserve

San Francisco-based bag company Waterfield has been in business since 1998, making a range of storage gear in small batches in the city. I’d heard of the brand and its penchant for quality over the past couple of years, and was glad to see for myself when Waterfield sent across its new Executive Leather Messenger bag.

This is a seriously luxe affair, made of leather and built to lovingly hold your gadgets while you jet around the world. It’s exceptionally well made, so you can expect it to last for years to come. It also costs upwards of $380, depending on which size you choose. Still, I’m happy to recommend it to anyone who’s looking to drop some coin on a handsome gear bag. Here’s why.

Design and features

The Executive (that’s what I’m calling it) is made of gorgeous full-grain distressed leather; the ‘grizzly’ option is a lovely tan brown that looks like it’ll develop a much nicer patina over time than the more polished black variant. There’s just one buckle on the front, which means there’s little to distract from the texture of the material.

Waterfield says the buckle it’s used actually comes from paragliding equipment, and is imported from Austria. Marketing spiel aside, it feels sturdy and is delightful to use. There’s also a leather grab handle at the top, and a nylon shoulder strap with a thickly padded shoulder pad that’s suitable to wear across your body or on just one side.

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Lift the flap, and you’ll find a well-appointed interior with gold trim that helps you easily spot your belongings inside. There are two sizes available: the compact one has a capacity of 7.5 liters, while the full (which I’m reviewing) measures 10.5 liters. If you’re anything like me and pack several items often rather than pack light, you’ll want to opt for the full size.

Your laptop – up to 15 inches – and tablet get their own compartments, with plush lining; the latter is also used in the two exterior pockets that can comfortably hold your phone and glasses case. There’s more room in the bag for your other stuff, and a couple of interior pockets for smaller items. Lastly, there’s a panel on the rear that lets you slip the bag on the vertical handle of your rolling suitcase, so you can breeze through airports with both pieces of luggage.

Using the Executive

There’s a lot to love about this bag: the thoughtful use of materials kept my gadgets from moving around much and getting scratched, and they were easy to see, thanks to the bright interior trim.

My laptop, an aging Dell Inspiron 7548, is among the larger 15-inchers you’ll come across. It just about slides into its padded compartment, which means that a bulkier one – like a gaming laptop – probably won’t fit. I had no issues with smaller MacBooks, though; the same goes for my old iPad in the smaller compartment.

Now for the not-so-great bits: I’m not a fan of the nylon shoulder strap. It seems like it may not last quite as long as the rest of the bag, and it detracts from the overall look of the otherwise posh Executive. Plus, the messenger itself weighs 1.4kg (3.25lb) on its own. That’s about the same as many other leather bags with a similar form factor that I looked at – but it’s certainly heavier than bags made from more modern materials. So be prepared for a bit of heft on your shoulder.

Who’s this for?

If you’re all about a stylish everyday carry kit and can appreciate something that ages with time, you’ll be hard-pressed to find a messenger that has more character than the Executive. The leather that Waterfield has chosen to go with is absolutely gorgeous, and has got me more compliments than any of my other accessories over the past few weeks.

That said, this is a pretty pricey option in the world of messenger bags for gadgets. Heck, it’s the second most expensive one in Waterfield’s line-up. If you’re keen on distressed leather and want to spend less, consider other bags from the brand, like the Vitesse at $169.

If you’re sold on the look and functionality of the Executive, I highly recommend opting for the grizzly colorway over the black one. Find it in two sizes on the company’s site: compact ($379), and full ($399).