I have a Courierware messenger bag in medium. It has lots of pockets including a rear outside pocket that is handy for separating wet clothing away from the contents. I paid extra for the padded strap and it definitely needs it otherwise the wide nylon strap tries to divide me into asymetrical halves. The flap is kept closed by large patches of Velcro as well as sturdy clips and straps. There is no stabilizing strap and that's my biggest complaint because it has a tendancy to slide around. It wasn't advertised as waterproof but it did claim to be weatherproof. I find the cordura fabric sucks up water like a sponge and while it doesn't soak the contents it certainly dampens them. I think it cost me about $110 US six or so years ago. I don't use it while cycling any longer but it is excellent for regular use off the bike or shoved into my bike basket. The thing wears like iron and shows absolutely no wear and tear. If I could add a stabilizing strap I'd absolutely wear it cycling. And it is a lovely shade of purple. I'd give it a 60/100 for bike usage but an 80/100 for regular off the bike usage.