Waterfield Designs Executive Leather Messenger review: Professional practicality
iMore - September 8, 2019
“When you want to make a statement with your laptop bag, look no further.”
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Device-specific
Fits new MacBook Pro M5
Handcrafted from full-grain leather, this classic messenger bag has modern features for today’s digital lifestyle: padded laptop and tablet compartments and ample pockets for storing tech gear.
Materials:
Dimensions & Weight:
14.25” (l) x 2.75”-3” (w) x 10.5” (h); 3.25 lbs.
36.19 (l) x 6.98-7.62 (w) x 26.67 (h) cm; 1.47 kg
Volume: 7.5 liters
15” (l) x 3.25”-3.5” (w) x 12” (h); 3.5 lbs.
38.1 (l) x 8.25 (w) x 30.48 (l) cm; 1.58 kg
Volume: 10.5 liters
The Executive Leather Messenger Bag is available in two sizes each with a built-in padded compartment for laptops and tablets. The following devices can fit in these sizes:
Compact - Laptop Compartment fits devices up to 14.09" x 9.7"
Compact - Tablet Compartment fits devices up to 13" x 8.75"
Full - Laptop Compartment fits devices up to 14.25" x 9.75"
Full - Tablet Compartment fits devices up to 13.5" x 8.5"
My first product from here and I love it. Well put together with high quality material.
I’ve put almost half a million miles on my WaterField Executive Messenger Bag, and somehow this thing looks better today than when I bought it. Airports, client shoots, coffee spills, overloaded laptops, being crammed under airplane seats… it’s taken an absolute beating and just keeps going.
And the customer service? Unreal. After 5 years, I finally had an issue with it. I reached out, and before I could even finish being annoyed about it, a replacement was basically already on my doorstep. That level of support is rare these days.
At this point, WaterField isn’t selling bags — they’re selling lifetime companions for people who abuse their gear for a living.
Unfortunately, I’ve now made the dangerous mistake of browsing their website again to see what I want next. My wallet would like to formally file a complaint.
Was hesitating for a while to purchase a Compact Leather Messenger bag since I am located in Belgium and was afraid that delivery and tax / customs management would be a hassle. Asked my questions to the service team and got very clear reassuring answers so gave it a go. Received my product very fast and dealing with customs was relatively easy. Overall, super happy I finally ordered that bag. It is beautifully crafted and unlike any other from the competition. Would buy again, only this time sooner ;)
I just love the WaterField bags and backpacks. They stow away all my gear efficiently structured and look awesome. I am happy about the different sizes. I got two backpacks and two messenger bags to match the duration of my travel. Thanks for making me look and feel good while on the go.!
I hesitated to purchase this bag, and now that I have it, I wish I bought it sooner. Traveling with this bag was a breeze - the luggage strap was the mvp. Craftsmanship and leather quality are top notch. While the bag is spacious, you do need to be mindful of what you’re carrying so that it doesn’t get too bulky. This is where I feel like an extending bottom buckle strap would have helped. Also wish it had swivel straps for better movement with it. All in all, this is a great bag and I would recommend to anyone looking for a leather messenger bag.
iMore - September 8, 2019
“When you want to make a statement with your laptop bag, look no further.”
![]()

The All-Leather Collection brings together premium full-grain leather designs that balance refined style, everyday functionality, and rugged dependability. Each bag is built to last, with smart details that make everyday carry easier. Check out the full collection.
The authentic, full-grain leather we use to make the Executive Leather Messenger is absolutely beautiful. See it, touch it, and you'll be hooked.
The distressed leather develops a beautiful patina, and your bag will age well as the years roll by.
We usually recommend not doing anything to the full-grain leather of your bag, letting it develop it's own beautiful patina over time. However, you may want to freshen it up a bit with a leather conditioner. The leather may darken a bit, so test the reaction first on a spot that's not highly visible, like the bottom of the bag. For the distressed leather that we use, you can also spread the oils around and smooth them out a bit with heat from a hair dryer.
We're proud to offer American-made gear built for the long haul. All our products are designed and made in our San Francisco workshop, where rent is high, labor expensive, and competition intense. We wouldn't go anywhere else.
My first product from here and I love it. Well put together with high quality material.
I’ve put almost half a million miles on my WaterField Executive Messenger Bag, and somehow this thing looks better today than when I bought it. Airports, client shoots, coffee spills, overloaded laptops, being crammed under airplane seats… it’s taken an absolute beating and just keeps going.
And the customer service? Unreal. After 5 years, I finally had an issue with it. I reached out, and before I could even finish being annoyed about it, a replacement was basically already on my doorstep. That level of support is rare these days.
At this point, WaterField isn’t selling bags — they’re selling lifetime companions for people who abuse their gear for a living.
Unfortunately, I’ve now made the dangerous mistake of browsing their website again to see what I want next. My wallet would like to formally file a complaint.
Was hesitating for a while to purchase a Compact Leather Messenger bag since I am located in Belgium and was afraid that delivery and tax / customs management would be a hassle. Asked my questions to the service team and got very clear reassuring answers so gave it a go. Received my product very fast and dealing with customs was relatively easy. Overall, super happy I finally ordered that bag. It is beautifully crafted and unlike any other from the competition. Would buy again, only this time sooner ;)
I just love the WaterField bags and backpacks. They stow away all my gear efficiently structured and look awesome. I am happy about the different sizes. I got two backpacks and two messenger bags to match the duration of my travel. Thanks for making me look and feel good while on the go.!
I hesitated to purchase this bag, and now that I have it, I wish I bought it sooner. Traveling with this bag was a breeze - the luggage strap was the mvp. Craftsmanship and leather quality are top notch. While the bag is spacious, you do need to be mindful of what you’re carrying so that it doesn’t get too bulky. This is where I feel like an extending bottom buckle strap would have helped. Also wish it had swivel straps for better movement with it. All in all, this is a great bag and I would recommend to anyone looking for a leather messenger bag.
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