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 new 14-inch MacBook Pro and 16-inch M1 Pro/Max MacBook Pro

-197 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 89 reviews
BC (Florida, United States)
Best bag ever!

The bag is roomy and the leather is amazing. I highly recommend this bag!

Trent B. (Wisconsin, United States)

Executive Leather Messenger

Jeffrey M. (Washington, United States)
Tip top

I was really tired of buying bags that had hardware failures or were unfinished looking on the interior. This looks great and I am sure it will be my last one. Semi- retired and working as a consultant…should make that journey.

John S. (California, United States)
Great bag! The strap needs work though...

I love this bag! The Grizzly leather is terrific, soft but rugged. I like the buckle as well and the overall design. Extremely well made like all the other SF bags I own. One of my favorite SF bags to date! But, the strap. I feel it should be removable as I like to use the bag as a brief as well. The strap can be tucked and hidden in the slot on the back of the bag but why? My biggest issue though is the strap makes noise when I use it and it actually sends tiny vibrations through the strap due to the material and design of how it attaches to the loop ring (see photo). My solution, I cut the strap off and have one of the Supreme Suspension Straps on order. It was that bad, at least for me. The only other small complaint I have is the flap doesn’t completely cover the ends of the bag. This can leave the inside of the bag open to weather and “other stuff”. Finally, I purchased the small size and it is a bit tight for a 2019 16 inch MacBook Pro. This isn't an issue at all, just an observation. Overall, highly recommended except for that strap!

Marian M. (Tyrol, Austria)
Practical piece of everyday art

It’s beautiful, it’s really well made, the grizzly leather is absolutely awesome and the full size is perfect for my 22 MacBook Pro 16“ plus some stuff. It was nearly 600 Euro with taxes and shipping to Europe but it’s really worth it.

{ diy['media1_title'] }}

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 Book 3 (13.5")
  • Surface Laptop 4 & 3 (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 with Magic Keyboard
  • 11” iPad Pro with Magic Keyboard
  • 11" iPad Air with Magic Keyboard
  • Pixel Slate
  • Surface Pro X, Pro 8, Go 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
  • MacBook Air M2
  • Surface Book 3 (15")
  • Surface Laptop 4 & 3 (15")

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

  • 12.9" iPad Pro with Magic Keyboard
  • 11" iPad Pro with Magic Keyboard
  • 11" iPad Air with Magic Keyboard
  • Pixel Slate
  • Surface Pro X, Pro 8, Go 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. 

You may also like