I carry a bag with me when I go places. I usually have some sort of electronic device, a camera, maybe some sunglasses, other assorted junk — more than will fit in pockets. I used to use army surplus canvas shoulder bags, but the quality dropped so fast during the 90s that eventually they would only last a year or two before developing major holes. Eventually I gave in and bought a Timbuk2 custom messenger bag. That was over 10 years ago. Since then, I’ve used it practically every day. Any time I leave the house, it goes with me.
Today I finally decided the bag was too scuffed up and faded, and looking embarrassingly shabby, so I’ve ordered a new Timbuk2 messenger bag.
I’ve gone the custom route again, partly because I’m now aware that I wear my bag left-handed, and partly because I wanted a custom design with waterproof fabric and reflective edging. What surprises me is that nobody else seems to be competing with Timbuk2. If you want a shoulder bag, and want it to last, I recommend them.