Baileyworks Messenger Bag

In times of yore, before it was possible to send documents over phone lines (via fax machines) or through cyberspace, many urban businesses relied on bike messengers and their courier bags to safely transport documents. Years later, bike commuters, travelers, and all sorts of everyday people now use bags that have roots in courier culture.

As a former New York City courier myself, I have some opinions on these bag types. One of my faves? The recently released Baileyworks Digital Superpro is an updated version of an existing Baileyworks bag that’s been one of the more popular bags for working messengers of the last decade.

There’s good reason for their popularity. The bags come in multiple sizes, are bullet-proof, designed well, and they are made by a cool factory in New Hampshire. I got my first Superpro about six years ago, and when I broke a clip on it (my fault), I called the company and spoke to the owner himself, Jon Bailey. He soon had a gratis replacement in the mail.

After hundreds of days on my back and countless grocery hauls, the bag is in good shape still. And that’s why I’m so stoked on the Digital Superpro, which contains the same, great attributes as my old bag but with an additional sleeve for my laptop.

Old attributes include two front pockets, one of which has a sleeve for pens and a pocket for a notepad. Those two pockets also pull double duty on the return trip from the grocery store as wine carriers (keeping two bottles from banging into each other).

Inside, there’s a bigger pocket with a zippered sleeve for items you need to keep as secure as possible – and it will accommodate an iPad. Other nice features include a stability strap, which can easily be tucked away if you don’t want to use it; two reflective strips; a phone holder on the primary strap; and a place for a blinkie light on the flap.

The padded laptop compartment does a good job keeping my computer in place. And it’s in the center of the bag to keep it away from my back. And the strap has a well-placed smart phone holder, is incredibly easy to tighten and has a great quick release function, which anyone who carries heavier loads will appreciate, because it’s really difficult to loosen a bag when it’s weighted down.

Want a second opinion? Lauren Klein, a former bike messenger and current Ph.D student, who commutes 10+ miles daily in New York City, also tested this bag for Gear Junkie over the winter.

Although the medium-size Digital Superpro was larger than Klein needed for day-to-day riding, she utilized it for large hauls from her food co-op. Klein appreciated how “comfy, simple, incredibly functional, easy to adjust, and extremely waterproof” the bag was. She also liked the reflectors and external cell-phone pocket.

At $219, Baileyworks’ Digital Superpro is one of the most expensive bags in the category. But it’s likely to last a decade. And if you’re one of those folks who go to the farmer’s market and don’t mind paying some extra cash so the folks on the other side of the table can make a decent living, it’s a great choice.

—Stephen Krcmar has worked as a bike messenger in New York City and Boston. He currently lives in Mammoth Lakes, Calif.