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"
I've had this bag since 2023, and it's been with me to London, Paris, Taiwan, Tokyo, Dublin, as well as work every day.
I've flown with it, biked with it, hiked with it. It's gotten wet and dirty and it still looks as great as the day I got it.
No part of it feels worn out or failing, and it still looks good and impresses when I'm meeting an important client.
10/10
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.!
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.
I've had this bag since 2023, and it's been with me to London, Paris, Taiwan, Tokyo, Dublin, as well as work every day.
I've flown with it, biked with it, hiked with it. It's gotten wet and dirty and it still looks as great as the day I got it.
No part of it feels worn out or failing, and it still looks good and impresses when I'm meeting an important client.
10/10
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.!
July is Travel Month
Whether you're travelling by plane, train, or car, our travel gear helps you stay organized. This month, we're refreshing our Packable Bags and a new community-designed travel bag debuts. Check out the schedule on What's Next.
Get out and ride
Put your gear in the Cycling Tote and head for your ride. Designed specifically to hold the gear you can't do without — cleats, water bottles, helmet, arm sleeves, sun block, etc.— and wouldn't want to forget.
Design with us
Unleash your inner bag designer and participate in our latest project — developing the ultimate 48-hour travel bag. Is this something you've been looking for? What would you use it for? Join other customers and help shape what this might look like.
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