When I was in junior high it wasn't cool to wear a backpack, so I carried my books and papers in a Nike gym bag every day. I broke several straps and it possibly gave me scoliosis.

In high school I had greater distances to travel, and it didn't seem as uncool to use a backpack. Most of the time we tried to use only one strap, however.
When I started commuting into Manhattan for TDG, I noticed that most of the designers, photographers and other cool-looking guys carried messenger bags. So for close to a year I slung over my shoulder a hemp messenger bag by Ecolution. I loved that bag, and I enjoyed the contrast to all the Prada-clutching fashionistas in my office building.
But the hemp bag is no more, as it gradually disintegrated under the weight of my laptop and books (and Coronas) for the train. I went looking online for another green bag, and happily discovered pieces made from recycled billboards. Water resistant! I had wanted to buy from District Cotton, because they look cool and are made locally in the city. But at the time they didn't offer any of the larger commuter sizes, and I need a lot of storage room since I tend to have long days away from home.
I ended up going with another brand (which I can't find online now). After about a year of happy toting that bag bit it too, coming to pieces on a walk near Rockefeller Center. What would Tina Fey think?
That bag has now been replaced, by an act2 messenger bag from GreenSmart. These babies are also water resistant, and I've long been happy with my laptop cozy from them (thanks Starre!). The cool part is that GreenSmart makes their bags from 100% recycled bottles, so it's a great way to promote recycling, and a fun talking point to impress eco-geek chicks.
I have to say I was hesitant about the vertical orientation of my GreenSmart bag, and I don't think I would go that route again. I think I'm a horizontal man after all. I wish there were more intermediate pockets, as I'm constantly fishing for small- and medium-sized items. But the bag has been durable, it offers some decent padding for my laptop, and I think it looks pretty good.
My GreenSmart bag doesn't make quite as bold of a statement as my old billboard bag, but it's serving me well, and it's one more piece of the reuse chain.
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