For the past few years when traveling for a few days, camping overnight, or a long week plus journey I’ve used a large simple yet durable REI backpack I’ve owned for about seven years. I’ve supplement that with this small messenger bag by High Sierra, which has sufficed as my “daily around town” bag too. But it suffers one from one atrocious design flaw: The worthless handle pictured at the top. The handle is connected to the front flap, which is only secured to the bag by two small strips of velcro. When lifting the bag by the handle, (which I never did), it awkwardly yanks the front flap up dangling the bag below. There’s absolutely no point in having the handle unless you’re transporting a bunch of feathers, and even then I’d have my doubts.

Since I’ve been using the Timbuk2 Classic Messenger Bag this past month, my travel attache has been both expanded and compacted at the same time. I wanted to upgrade to something large enough to take on long trips, yet small enough to bike and walk around the city with every day.

Timbuk2 has been around forever, and is the staple for most messenger bags. Other bags such as Chrome have improved on their design and durability, and Ortlieb has filled the niche for high quality hard shelled bike bags, but I’m happy with Timbuk2′s design, support, and selection.

The most practical feature is the chest strap that stabilizes the bag on your back. This distributes the weight while preventing it from shifting while walking fast or biking. A simple concept, but often overlooked. The shoulder strap is QUICKLY adjustable, so whether you have a laptop and six books inside for school, or just your lunch and some bills to mail, it’s easily adjustable via the side strap clasp. And look at all this freakin’ space! I can easily fold up a few shirts, pants, personal sundries, books, and have room for more.

Timbuk2.com