Timbuk2 Classic Messenger Bag review: Stylish update to an urban icon

There was a time when a trip downtown was filled with the hustle and bustle of people. And a lot of those people sported Timbuk2’s Classic Messenger Bag–not just bicycle messengers, but also commuters going to work, tourists sightseeing, and anyone else trying to get where they need to go. The Classic Messenger Bag became more than just a bag. It became an urban icon.

Times change, though. Downtown isn’t what it used to be–there are fewer people going to the office, delivery from Uber and DoorDash has replaced bike messengers, and tourists aren’t packing the street like they once were. Timbuktu’s Classic Messenger Bag has changed, too, and while it was always a great bag, it’s become even more versatile for the times when you go out–downtown, the suburbs, the park, the beach, on campus, wherever.

Classic Messenger Bag design

What makes the Classic Messenger Bag so appealing is that it’s designed for quick and easy access. Just flip open the front flap and your stuff is within easy reach. Close the front flap and it’s secured with Velcro and a couple of adjustable latches.

I tested the large Classic Messenger Bag, which has plenty of room inside for a 16-inch MacBook Pro and other gear, so much room that it can slide back and forth in the bag. You might find that unsettling, though, so for a snug laptop fit, consider the medium or small sizes.

The inside has three large compartments, with the middle section ideal for a laptop, tablet, or documentation. The front compartment is a better fit for bulky items, like shoes, a water bottle, or boxes. The back compartment is where everything in-between can go. There’s also a four-pocket section for items like pens, USB drives, etc. and a zippered pocket. It’s not full of holders like some backpacks or other bags, which may or may not be to your liking.

Underneath the front flap is what Timbuk2 calls a Napoleon pocket. On the large and medium bags, it has zippers on each side, and you can reach this pocket through the side openings when the front flap is latched. It’s a great place to put keys, a phone, or an earphone charging case, anything you need on hand but don’t want to have to go inside the main part of the bag. Again, it’s all about quick access.

The Classic Messenger Bag is made of Eco Cordura, a synthetic material made using recycled materials. It’s durable and weatherproof, and the interior has been upgraded with a Thermoplastic Polyurethane waterproof liner. The bag is available in a wide variety of colors, and customers can personalize their bag by picking different color panels.

Carrying the Classic Messenger Bag

The Classic Messenger Bag has always had a single strap, but Tikbuk2 redesigned it with sateen webbing that’s soft and durable, and it can be removed and switched for left- or right-handed wearing. The adjustment buckle has also been redesigned; in the prior version, it was plastic, but now it’s aluminum, which makes it feel sturdier as you adjust it.

The main issue some people have with messenger bags in general is that a single strap means there’s a single pressure point on one shoulder. Timbuk2 includes an Ortholite shoulder strap to alleviate the pressure a bit, but there’s no way of getting around the fact that it fits differently from a backpack. Depending on what you carry, it may not be comfortable, so if you’ve never used a messenger bag before, it’s a good idea to see how it fits before buying.

The straps for the flap latches have reflective tabs to make you more visible in the dark. When customizing a bag, Timbuk2 offers three reflective fabrics for the body panels of the bag to make yourself even more visible if you’d like. 

Should you buy the Classic Messenger Bag?

Even though the urban landscape has changed, the Classic Messenger Bag endures. It’s a top-quality, stylish bag, designed with plenty of pockets and compartments for different types of stuff. While the bag is a great general carry-all, it’s ideal for someone who needs quick access to what’s inside. But if your primary item is a laptop, look at the medium or small sizes.