Executive Leather Messenger
Executive Leather Messenger
Our distressed full-grain grizzly leather only looks better with age
Grizzly leather's beautiful patina (Pictured: Staad Attaché)
Two deep organizational pockets (one zips closed)
Two padded laptop and tablet compartments
Compact fits up to a 15" laptop and your work essentials
Full sizes accommodates bulkier items
Designed for comfort: ergonimically-placed handles, adjustable straps
Slot for carry-on handles
Compact and Full sizes
Full size, Grizzly Leather
Available in three full-grain leather colors
Chocolate Leather
Grizzly Leather
Black Leather

Executive Leather Messenger

Fits Apple's 14-inch MacBook Pro and 16-inch M1 Pro/Max MacBook Pro

-248 in stock

Handcrafted from full-grain leather, this classic messenger bag hosts modern features for today’s digital lifestyle: padded laptop and tablet compartments and ample pockets for storing tech gear.


All our products are crafted locally in our workshop by the most skilled sewing team in San Francisco.


  • Full-grain, naturally tanned leather
  • More details here

Dimensions & Weight:

  • Compact:
  • 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

  • Full:
  • 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


  • Metal key fob facilitates convenient key retrieval.
  • Dual-layer leather flap shuts securely with a paragliding buckle.
  • Gold, water-resistant liner lights up interior for increased visibility.
  • Two padded compartments for protecting a 16-inch laptop and 13-inch tablet.
  • Rear panel slides over wheeled-suitcase handles for hands-free airport navigation.
  • Leather grab handle, secured with strong rivets, offers a more formal carrying option.
  • Adjustable shoulder strap with a removable floating shoulder pad keeps strap in place.
  • Luxuriously-soft, lined pockets under front flap holds a smartphone and other quick-access items.
  • Interior pockets include one zippered for valuables, open-topped for cords and accessories, and one pen slot.


  • Domestic: Flat rate 2-day shipping.  Details.
  • International: 2-3 business day delivery. Country duty/tax calculated at Checkout. Details.

Customer Reviews

Based on 97 reviews
Robert C. (Florida, United States)
Exactly what I hoped it would be.

Classy looking with a slim profile, but with plenty of room for my MacBook and accessories. Highly recommend.

I W. (Texas, United States)
Beautiful and exactly what I needed as an executive

I’ve been looking forever for ‘the right’ product. This is a perfect blend of material, and style that serves like a briefcase but is stylish like a modern messenger. Travels so easily as well as I’m on a flight every week. Only thing it’s missing is a small area to quickly tuck items into (keys, AirPods, etc). I love it and so worth the money!!

Edwin G. (Texas, United States)
Executive Leather Messenger

They say Alexander the Great captured the known civilizations of the globe before turning 30 and wept for there were no more worlds left to conquer. In a way I feel the same about my new Executive Leather Messenger. It is simply the best. There is no better. The smaller version -- which I have -- is the perfect Every Day Carry for someone who wants to look professional, and feel professional, and still practice minimalism and not feel like a work horse when carrying it. I can fit my 13 inch MacBook Air, My 11 inch iPad Pro and even the Remarkable2 in with ease. I know it's not my last Waterfield bag, but I also think it is the pinnacle of the great quality for which the company stands. It could not be better.

James H. (Illinois, United States)
Great Professional bag

It's a great leather bag that's both professional and has a playfulness around it like the buckle. I got the compact which is good for my needs but I can see most people going for the regular as it's not as flexible as you'd imagine so you won't be able to stuff too much in it. the fuse reel for your apple charger will only fit in the front pockets or open in the middle section of the bag and not the inner pockets. it's a good bag

Paulo H. (Colorado, United States)
Executive Messenger bag in Grizzly Leather

Outstanding quality, build, and stye. My only gripes are minor but the strap not being attached with swivels or being detachable. That would've made the bag perfect. Other than that, I love this bag. I will certainly continue building my collection.

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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.”

4.5 out of 5 stars


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" 

  • 14" MacBook Pro M1
  • 16" MacBook Pro M1 (snug fit)
  • 13” MacBook Pro M2
  • 13" MacBook Air M2
  • Surface Laptop 5 (13.5")
  • Dell XPS 13
  • Lenovo X1 Carbon Gen 7

Compact - Tablet Compartment fits devices up to 13" x 8.75" 

  • 12.9" iPad Pro M2 with Magic Keyboard
  • 11” iPad Pro M2 with Magic Keyboard
  • 11" iPad Air with Magic Keyboard
  • Pixel Slate
  • Surface Pro 9 with Type Cover

Full - Laptop Compartment fits devices up to 14.25" x 9.75" 

  • 14" MacBook Pro M1
  • 16" MacBook Pro M1
  • 13" MacBook Pro M2
  • 13" MacBook Air M2
  • Surface Laptop 5 (15")

Full - Tablet Compartment fits devices up to 13.5" x 8.5" 

  • 12.9" iPad Pro M2 with Magic Keyboard
  • 11" iPad Pro M2 with Magic Keyboard
  • 11" iPad Air with Magic Keyboard
  • Pixel Slate
  • Surface Pro 9 with Type Cover


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. 

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