Based on my history, I think you could say that I have pretty awful luck when it comes to messenger bags. One of my first messenger bags came free of charge with a subscription to a now defunct magazine called Cargo that was meant to be the men’s version of Lucky magazine, a shopping magazine. I honestly got the subscription because it was ten dollars and came with the bag.

It took about a year and a half of daily use before that bag eventually tore at the straps and became unusable. I waited for an inexpensive way to get the bag repaired. I didn’t want to pay more for the repair than I did for the bag. While I was selling buttons at a craft fair, I came across a booth of a small company that made clothing for children as well as excellent messenger bags. Sadly, that bag also developed a rip over the course of a year and a half.

I got a third bag last year while Elizabeth, Chaim, and I were in California. My wife Elizabeth’s mother had brought a bag that Elizabeth’s brother had gotten at a thrift store for twenty-five cents. It was a great bag with a solid strap but had an irritating aspect which was that in order to take anything out, you had to turn it upside down and unzip nearly the entire circumference of the bag — the bag doubled as a three ring binder which I never used. I ended up using only the front pouch which could barely fit anything I wanted, which made it a completely useless bag.

I finally found what seems like the right bag in the Rickshaw Small Zero Messenger bag. I was concerned as to its size and so I contacted the company and sent them a list of what I usually carry in my bag — iPad, iPod, a book or two, a tumbler for coffee or water bottle — and they wrote back that day to say that there would be no problem.

One of the things that attracted me to the bag is that it is hand crafted in San Francisco. I think one of the problems with most of my past bags is that they were massed produced in the cheapest way possible and the end result was that they were poor in quality. I have been holding out on writing this review as long as I have because I wanted to see how well my bag would hold up and despite nearly a year of daily rough usage, it looks and feels like it did the day that I got it.

The interior features not only a lot of room but a couple of smaller interior pouches, perfect for holding pencils and other such small items. The strap adjusts easily and it distributes the weight of the contents of the bag beautifully.

I got the bag made in the black waterproof sailcloth option because when it rains here in New York, it can really come down as a deluge and sometimes an umbrella just is not enough — I am happy to be able to tell you here that nothing I have ever put in the bag has gotten wet even during the most intense of downpours.

This will not be my last Rickshaw bag review — a few months after buying the Small Zero Messenger Bag I got a courier sized messenger bag to use at my office — same colors, same materials, just a lot bigger! I hope to review that when I have had it for a full year. Meanwhile, please do check out Rickshaw — you can even have them tweet a photograph of your bag after it has been made.

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