If you’re looking for a good jacket or bag, you have your choice of materials: leather, heavy nylon, waterproof synthetic weaves like Gore-Tex… but for my money (and not a little of it either) the king of them all is waxed canvas. Pliant yet protective, wind and water-resistant but breathable, handsome to start but grows a character of its own, waxed canvas strikes, for me, the perfect balance of attributes. I drape myself in it, and in the case of bags, drape it from myself.
The main caveat is that it is not is cheap — sure, you can get a bag for $30 or $40 on Amazon, but if you want something that will live for years and years and get better with age, you’re going to be spending quite a bit more than that.
The bags here are expensive, but like leather the craftsmanship and material quality matter a great deal in whether you end up with an item that deteriorates steadily or comes into its own. Like so many things, you get what you pay for — up to a certain point, of course.
I’ve collected bags from a variety of producers and tried them all for the last few months during everyday use and trips out of town. I focused on the “fits a medium-size laptop with room for a couple of books and a camera” size, but many of these makers have plenty of variety to choose from.
Check the galleries under each bag to see examples of anything I pick out as nice or irritating. (The galleries are all really tall because of a bug in our system. Don’t worry about it.)
ONA Union Street ($299) and Brixton ($289)
Pros: Rigidity and padding,...