This is the messenger bag Don Draper would carry

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Briefcase messenger bag
Perfect for the office, or the martini bar
Photo: SF Bags

Look, it’s yet another beautiful bag from San Francisco’s WaterField Designs. The Executive Leather Messenger is a modern take on the briefcase, designed for MacBooks, iPads and chargers, instead of clipboards, papers and cigarettes.

That’s not to say that you can’t take this to a martini bar, or fill it with analog vapers and “artisanal emails” (aka written letters), if you want to.

WaterField Designs Executive Leather Messenger

WaterField Designs Executive Leather Messenger comes in two sizes.
This leather messenger bag comes in two sizes.
Photo: SF Bags

The Executive Leather Messenger is just that — a leather messenger bag that looks equally at home in the bored1 room as it does in a hipster coffee shop. The (removable) shoulder strap connects via D-rings that are situated relatively low, so it stays comfy on the shoulder or slung across your body.

Inside, you’ll find a laptop pocket, an iPad pocket and a couple of other pockets for cigarettes and chargers. Both the pockets and the main section are lined with WaterField’s gold liner, making stuff easy to find. (I own several WaterField bags and I love this feature.)

Obligatory Clooney mention

The Executive Leather Messenger should age beautifully.
The Executive Leather Messenger should age beautifully.
Photo: SF Bags

I also love that the leather in these bags is designed to age beautifully. As it wears, it looks better and better. I still have an old WaterField Franklin Tote, aka the George Clooney of Bags, and it continues to improve. Unlike the real George Clooney, who will, despite the best efforts of Hollywood diets and doctors, wither, slacken and crinkle, expiring long before my Franklin Tote schleps its final picnic.

Details

Golden pockets.
Golden pockets.
Photo: SF Bags

There are a few other nice details to mention. One is the Austrian paragliders’ buckle, which has a satisfying clunk and is easy to open (as you’d hope, if you were an actual Austrian paraglider). Another is the pair of plush-lined pockets on the front, perfect for iPhones. And finally, the harried business traveler’s favorite feature of all, a leather panel that slides over your rolling suitcase handle while navigating airports.

Fill it up.
Fill it up.
Photo: SF Bags

I dig this bag. It comes in two sizes, compact and full, for $379 and $399 respectively. You can also choose between black leather and grizzly (!) leather. Not cheap, but in my experience, bags don’t come much better built than WaterField’s.

Buy from: WaterField Designs

  1. No, this is not a misspelling.