The Timbuk2 Classic Messenger Bag is a top-quality messenger style bag that can be carried in either hand. With its workhorse design and attention to detail, this durable backpack offers an excellent balance between durability and comfort for those who need their gear wherever they go.

The messenger bag, ah, the simple messenger bag. These bags, which got their name from their extensive usage in the postal service, have since grown in popularity for the school, commuting, and daily use—and after using the Timbuk2 Classic Messenger Bag for the last two weeks, we can see why.

Timbuk2 Classic Messenger Bag in DetroitThis bag includes a comfy shoulder strap that you can adjust to your desired amount of security, whether you’re carrying it crossbody or simply over one shoulder. It also provides enough space to hold your daily necessities while keeping them safe from the outdoors.

Aesthetics & Materials

The Timbuk2 Classic Messenger Bag is exactly what it says on the tin. However, we’re on the fence about the bag’s appearance, and our Instagram poll reflects that attitude. Only almost half of you (54 percent) liked the appearance, but your mileage may vary.

The Monsoon colorway, which has side-by-side black, navy blue, and grey fabric—it looks like a more subdued version of Neapolitan ice cream—has been put to the test. No worries if you’re searching for something a bit more vivid. At the time of writing, this bag was available in various hues and materials.

Timbuk2 Classic Messenger Bag Material and LogoThe Timbuk2 wordmark is embroidered on the front of this bag on a little white-on-black tag. You’ll see their logo on one of the shoulder straps and the end of the front straps—a swirl that represents a spinning bike wheel. Timbuk2 is recognized for its bike messenger gear, so this isn’t unexpected. The branding is meaningful and fundamental, which we like.

You may be wondering what this bag is composed of. The fabric is made of CORDURA® Nylon with a TPU (thermoplastic polyurethane) coating for further weather resistance. This bag isn’t waterproof, but it’ll keep you dry in the rain.

Timbuk2 Classic Messenger Bag ZipperThe zippers on this item are made by YKK, a manufacturer with which we’ve had a lot of good luck in the past. They’ve been operating nicely thus far throughout testing, as predicted.

Then there’s some Duraflex hardware, which is another well-known brand. We’re pleased to announce that everything has been running well in this area. There are no complaints!

Components from Outside

Left: Riley, Height: 5’4” (162 cm), Torso: 16.5 in (42 cm) | Right: Mark, Height: 5’10” (178 cm), Torso: 19” (48 cm)Before we go inside, there are a few things we need to take care of. The harness system is first on the list. It fits remarkably tight to the body, almost like a backpack, and is comfortable. Let’s look at it more closely.

The shoulder strap is coated with mesh for additional ventilation and includes substantial, adjustable cushioning. There’s a plastic adjuster you can use at one end to adjust the strap. We’ve discovered that it loosens more quickly than it tightens, but you can still generate some slack, swing the bag around to get what you need, then re-secure the strap in one fluid action.

Timbuk2 Classic Messenger Bag Shoulder StrapWe haven’t used this adjustment much since this bag also comes with a stability strap that makes it difficult to move the bag around to the front while it’s in use. We like how this strap keeps the load close to the body and distributes weight evenly for a balanced carry—both of which are useful for activities like riding a bike (or running into work after you hit snooze one too many times).

We don’t like how it attaches to the shoulder strap, however. It fastens using velcro (like Ricky Martin’s song, Livin’ La Via Velcro), and when we’re completely loaded, the velcro weights down the shoulder strap wherever it’s placed. It’s not a big concern since it doesn’t hinder the carry, but if it were fastened with something sturdier, like a buckle, it wouldn’t happen.

There’s velcro on the other end of this stability strap that you may use to remove it completely if it’s not useful to you or merely when you’re not using it. Then you may put it inside the bag to keep it out of the way and simple to access when you’re ready.

There’s also a handle towards the top that makes it easy to grip the bag. When not in use, this handle rests flat against the back panel and blends in with the surrounding fabric to maintain the overall look as unobtrusive as possible.

It does not, however, work well for carrying the bag in a briefcase manner. As we said previously, this bag lacks structure, so when you hold it up by the handle, it folds inward and becomes somewhat floppy. Keeping a laptop inside adds some rigidity, but we’re not lovers of using our pricey technology to accomplish the work that a frame sheet might do.

Timbuk2 Classic Messenger Bag Compression Straps We should also mention the numerous attachment points that are accessible. A look towards the bottom of the front of the backpack may be used to connect a bike light for increased visibility on those late-night journeys. Alternatively, use a carabiner to fasten your hat while you’re out in the wind. If you want to connect both of these or other gear, there’s also some plastic hardware on both sides of the bag that works for this.

The compression straps are the last item on our list to discuss. On one end, there are buckles to assist secure the main compartment, and on the other end, there are reflectors to aid with visibility on your late night/early morning travels. They may be adjusted to handle a bigger weight if necessary, and they can also be used to cinch the bag down when it isn’t completely filled to make it as small as possible.

When you cinch this bag down, some of the cloth on the bottom of the bag pulls up into the main compartment, which is something we want to point out. When you put items inside, it either falls into the wrinkles of the cloth or pushes them out, making the bag sagging.

The Inside of the Bag

We apologize for the length of the last segment, but we’re finally going inside this monster. So sit back and relax, since pockets are first on the agenda.

Timbuk2 Classic Messenger Bag Front OrganizationWhen you first unzip the bag, there is a little zipped compartment on the front. There’s also a bright red key leash in here, which makes it simple to find. We’re not concerned about the clip’s longevity since it’s made of metal and feels solid in our hands. But, so far, it seems to be up to the job.

On the other hand, the length is something we truly enjoy about this leash. We’ve tried a number of key leashes on other bags that are too short to open your vehicle or door without taking off the bag or unclipping your keys. While this one is long enough to reach whatever you’re unlocking without doing either, we appreciate the ease.

A sleeve hides below this pocket, which may also be used to store smaller objects. However, it’s worth noting that it doesn’t have any closing, so it’s not particularly secure—you shouldn’t put anything very precious inside.

These pockets are located on top of another bag that a side zipper can access. We haven’t kept anything inside since it’s so thin, except some Fulton & Roark Solid Cologne to keep us fresh throughout the day.

Timbuk2 Classic Messenger Bag Main Compartment OrganizationFinally, we arrived at the main compartment. You may clip the top flap into place for a more secure carry using the buckles on the compression straps, as we indicated before. This flap also has some velcro on it that is easier to disengage for when you’re taking things in and out during the day.

It has enough space for your daily needs and not much extra, with a capacity of 9L. You have some liner compartments on one wall that assist separate your more minor stuff in terms of organizing. There are more oversized pockets on both ends for items like a tiny notepad and an adapter and two sleeves in the center for pens, pencils, or even a stylus if you have one.

We’ve started throwing our leftover electronic accessories—chargers, a mouse (the computer sort), and the like—into another bigger zipped pouch behind these pockets. Because it’s the only pocket within the compartment with a secure clasp, you’ll want to store your most precious goods here.

While we like the organizational features, they are all centered on one side of the bag. The front of the bag sags due to the weight of everything within, and it doesn’t look good. It’s not the end of the world; we wish the pockets were more equally distributed throughout the compartment to spread the weight more evenly.

Timbuk2 Classic Messenger Bag Main CompartmentYou have two water bottle compartments on the inside. One is made of solid lining and isn’t as stretchy as the other. Constructed of mesh, and has a more excellent elasticity. We were able to fit a Hydro Flask Standard-Mouth Water Bottle with Flex Cap 21 oz perfectly inside one of them. Of course, if you’re carrying one bottle at a time, you can utilize the second pocket to store any more essential items you may have so they don’t get mixed up with the rest of your belongings.

Then you have some extra room to put your other belongings, such as a more significant set of headphones or a light jacket. You may supplement with pouches or packing cubes for your bigger goods rather than letting them float if you want even more orders. Remember that this bag might get uncomfortable if it is overstuffed, so don’t stuff it too full.

Timbuk2 Classic Messenger Bag Laptop SleeveFinally, you’ll discover a specialized laptop sleeve on the other wall that can accommodate up to a 16″ MacBook Pro. Unfortunately, it isn’t very well cushioned, and there isn’t even a fake bottom, so that you won’t receive any more support for your laptop. We suggest storing your gadget in a protective case because of this (and simply in general). Laptops are pricey and should be treated with care.

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