Waterfield Designs Executive Leather Messenger review: Professional practicality

When I got my MacBook Air at the start of this year, I knew I wanted to have accessories for it that would help keep it safe and protected, while also looking professional and classy. Another requirement for me is that the sleeves and bags I'm going to use with it should be high quality and will last me a very long time. That's why I like to depend on one of my favorite bag makers, Waterfield Designs, to get the job done.

I have had several Waterfield bags before, including the Field Muzetto, Bolt Cross Body, CitySlicker for Nintendo Switch, Sutter Sling for Nintendo Switch, and the VERO Sleeve. The Field Muzetto is my oldest (and first Waterfield) bag, but it's still holding up very well and in great shape. I've always turned to these bags when I want something that looks great and will keep my computers and devices scuff-free, even when traveling. So when I saw Waterfield releasing the Executive Leather Messenger bag, I had to give it a go.

Like with my other Waterfield bags, I'm not disappointed with the Executive Leather Messenger. If you're all about serious business and getting work done, then this is a fantastic investment.


  • High-quality, full-grain leather develops patina
  • Even Compact size is quite spacious
  • Padded compartments, plenty of organizational pockets
  • Adjustable shoulder strap with pad to keep it in place
  • Leather grab handle on top, suitcase handle on rear
  • Authentic paragliding buckle to secure everything


  • High price tag
  • No removable shoulder strap
  • Compact won't fit a 12.9 iPad Pro with other keyboard cases

I've always wanted a briefcase-style bag, and honestly, Waterfield knocks it out of the park with this one. You look like serious business when you're out and about with it.

Classy, elegant, and practical

Waterfield Designs Executive Leather Laptop Messenger: Features

Waterfield Designs Executive Leather Messenger clasp

What drew me to the Executive Leather Laptop Messenger originally was the fact that I wanted a briefcase-style bag that I could grab by a handle and then leave the door. This comes pretty close. Plus, the bag looks professional enough for pretty much anything, such as a board meeting, client presentations, sessions with your project team, going to the office, classes, and more.

The Executive Leather Messenger, like other Waterfield bags, is made from a superb, full-grain leather that is soft to the touch but retains a bit of ruggedness to it with rough edges. Since Waterfield bags are made to last a very long time, this bag is no exception. The leather will also develop a nice patina over time as well. So while I started off with the Grizzly leather, it will get darker as I use it more, similar to my VERO Sleeve (started Grizzly, now looks more like their Chocolate leather).

A hefty leather flap is what's between you and your stuff in the bag, and an authentic paragliding buckle clasp gives a satisfying click to secure everything inside. The clasp can be unfastened with one hand, making it easy to access your belongings.

Waterfield Designs Executive Leather Messenger empty interior

Since this bag is designed for taking care of business on your laptop, there are two padded sections on the interior. These are lined with a plush microfiber material that is soft and keeps your devices scratch-free. There is also a zippered pocket for valuables, an open-top pocket for accessories like cables and other small items, and even a pen slot for your Apple Pencil. The main compartment features Waterfield's signature and water-resistant gold liner that makes it easy to find what you're looking for. Nothing gets hidden or lost into a black abyss (as it seems to happen with every other bag I use). Plus, the metal key fob makes it easy to get your keys quickly when you need them.

Outside of the main compartment are two quick-access pockets for things you need quickly, like your smartphone, wallet, passport, and other necessities.

Waterfield Designs Executive Leather Messenger crossbody style

I got the Compact size of the bag, which will hold up to a 15-inch MacBook Pro with Touch Bar and an iPad Pro 12.9-inch with Smart Keyboard Folio. The Full size, which costs $20 more than the Compact, will fit up to the same size devices but fits with the 15-inch Retina MacBook Pro as well.

The shoulder strap is made of nylon material and is attached via sturdy metal D-rings. The D-rings help keep the strap in a comfortable position so that the bag is always against the body, whether you're wearing it over-the-shoulder or crossbody style. Unfortunately, the shoulder strap cannot be removed if you would prefer to just use the grab handle. To make up for it, the bag does come with a leather shoulder pad that attaches via button clasps and helps the nylon strap stay in place while you wear it.

Speaking of the grab handle, it's positioned specifically to be more towards the back, so that there isn't stress on the front of the leather flap. It also gives you a more formal way of transporting the bag itself and feels natural. And when you take the Executive Leather Messenger with you on business trips, the suitcase handle on the rear of the bag easily slides over the handle of your wheeled-suitcase carry-on.

Everything I need in one rugged yet professional bag

Waterfield Designs Executive Leather Laptop Messenger: What I Like

Waterfield Designs Executive Leather Messenger grip handle

I've been using the Executive Leather Laptop Messenger for the past few weeks when I go out to work remotely at a hip and trendy coffee shop, and it's holding up very well so far, as I'd expect.

As I mentioned, I got the Compact size of the bag, and it fits my MacBook Air in the VERO Sleeve comfortably in the laptop compartment with a bit of room to spare. I find the various pockets to be neatly organized and enough space for my various cables and chargers, and the Apple Pencil slot is a nice touch.

With Executive Leather Messenger, you get plenty of space for the essentials, and with several ways to carry it, you can make it work for you, not the other way around.

My favorite thing about this bag, in particular, is that parachute buckle in the front. These are imported from Austria and made from metal, so when you lock it, there's a nice click sound to reassure you that it's secure and you're good to go. Releasing the clasp is easy and fast, as all you need to do is slide a finger down on each side of the buckle to unlock and open. You also get that satisfying clicking sound each time you open the bag.

I also like the leather shoulder pad that comes with the bag. Usually, I have an issue with straps sliding around my shoulder as I go from place to place, but the leather pad really makes sure that the strap does not slide around or move at all.

While I don't do as much traveling as others, I appreciate the suitcase handle. The leather stretches out a bit and gives you enough leeway to slide it over your suitcase handle without much effort. Then you can give your shoulders a break and wheel it around the airport.

It can't be a true briefcase

Waterfield Designs Executive Leather Laptop Messenger: What I Don't Like

Waterfield Designs Executive Leather Messenger full interior

My biggest issue with the bag is the fact that you can't remove the shoulder straps at all. Sometimes I honestly would prefer to use this bag without the straps, just like a briefcase, but that's not possible. I understand that it's a messenger bag and it's designed that way, but it would have been nice to have the option.

I'm also sad that while the bag can hold up to a 12.9-inch iPad Pro with Smart Keyboard Folio, it won't fit if you have a different keyboard case. I am using a Logitech Slim Combo case, and I like to have the keyboard attached to the front to protect the screen. It turns out that my iPad Pro won't fit in the tablet compartment when this case is on, and it's just barely over in thickness. As a solution, I just stick the iPad Pro with the Slim Combo case in front of the tablet pocket if I need my iPad Pro with me.

If you're concerned about your iPad Pro not fitting, I would recommend going for the Full size.

A bag for the executives in all of us

Waterfield Designs Executive Leather Laptop Messenger: The Bottom Line

The Executive Leather Messenger Bag may be my new favorite bag so far. It has a practical form with plenty of room for your business essentials, with some room to spare. The paragliding clasp is such a nice feature and it makes you aware of whether or not the bag is secure. The shoulder strap, while not removable, is pretty flexible and comfortable to wear, especially with the leather pad. I am also a big fan of the grip handle at the top and the suitcase panel.

When I want to look nice and professional while working remotely, I will always grab Waterfield Designs' Executive Leather Messenger bag for the job.

Christine Chan

Christine Romero-Chan was formerly a Senior Editor for iMore. She has been writing about technology, specifically Apple, for over a decade at a variety of websites. She is currently part of the Digital Trends team, and has been using Apple’s smartphone since the original iPhone back in 2007. While her main speciality is the iPhone, she also covers Apple Watch, iPad, and Mac when needed.

When she isn’t writing about Apple, Christine can often be found at Disneyland in Anaheim, California, as she is a passholder and obsessed with all things Disney, especially Star Wars. Christine also enjoys coffee, food, photography, mechanical keyboards, and spending as much time with her new daughter as possible.