I often agonize over bag sizes. Part of me always wants to go bigger, just in case. But then I end up with messenger bags and backpacks that feel too bulky to carry around every day. If I opt for the smaller one, it’s often too small to fit the things I need and ends up overstuffed. The item I often carry with me that seems to complicate this issue is the 11-inch iPad Pro. It’s light but rigid, and in small bags it can feel like carrying around a plank of wood flapping against your leg. Smaller bags can also be too narrow, making it a tight fit for any other items you want to carry. WaterField’s Shinjuku Messenger aims to solve some of these problems with a design purpose-built for the iPad.

Everyday Carrying

Coming out of the box, it seemed way too small. There was no way this one was going to comfortably fit my iPad, water bottle, chargers, and other stuff. It seemed doomed to be one of the tiny messengers that couldn’t quite cut it.

Until I started putting stuff inside. The iPad slipped into the padded tablet sleeve with ease, a narrow water bottle fit comfortably at the bottom of the main pocket. The other inward-facing pockets were spacious and expanded a bit as I put in a charger, my wallet, a pair of earbuds, and a sunglasses case. There was room for everything, and the bag wasn’t even filled to capacity. Its exterior shape still felt soft and pliable, not taut and filled to the brim the way an overloaded messenger can feel. Flipping open the lid, everything was within view, and every item was reachable without moving anything—a must for any bag as far as I’m concerned.

Slung across my body, it didn’t even look like a messenger bag. Even fully laden, it looked smaller—more like a purse or just a small crossbody for your phone and a few other items. I also noticed how evenly distributed the weight felt. The straps attach to the bag itself at a slight angle, rather than being sewn on straight up and down; it’s just enough of a direction to the bag that it falls against your body nicely no matter where you have it slung—hip, lower back, front, across your chest, hung from one shoulder. It’s the kind of quiet, intuitive design flourish that tells you this bag was designed by people who know what they’re doing.

Adjusting the strap is also easy as you can lengthen or shorten it without taking it off. The strap itself is a thick weave, almost like a car seatbelt. It is a bit thinner than the straps on other WaterField bags I’ve used, and the edges are a little hard and can rub against your neck uncomfortably, though like other WaterField straps they’ll probably soften up over time.

The top flap seals with a magnetic closure. It’s strong and snappy but not so strong that you have to fight it. As with all magnetic closures though, I worry about their durability over time. I have a couple other WaterField bags I’ve tested, and the magnetic closures are still going strong on those, but I’ve lost so many bags to the wear and tear of magnetic closures abrading themselves free from canvas that I’m inherently distrustful. I didn’t notice any unusual wear and tear on the canvas where the magnets sit while testing, which is always a good sign.

The interior is bright orange with a textured pattern. That’s one of my favorite things about WaterField Designs. I’ve come to dislike bags with dark-colored interiors; it’s way too easy to lose things in the dark. Against a bright color, I can always spot a missing hair tie.

Canvas, but Different

I tested the black canvas version with leather accents on the flap. I was a little wary of its material construction; canvas can be finicky and scuff easily, or become waterlogged at the mere sight of a raincloud. This canvas, WaterField assured, was different. It’s a material called X11 Cotton from X-Pac, a company that spun off from Dimension-Polyant, a manufacturer of high-performance sailcloth. According to X-Pac, the material is a specially treated canvas with an inner layer of fibers woven in a diamond pattern to enhance durability and weight distribution, and it’s also water-resistant. That waterproofing is achieved via a PFAS-free DWR coating. X-Pac makes other DWR materials that do use PFAS, but I confirmed with WaterField and X-Pac that the X11 Cotton is PFAS-free.