What would you recommend for a laptop bag? My commute isn't very long - 1.5 miles each way, but I would like something that will last forever and is waterproof. My work computer is a 14" laptop and contains HIPAA info, so I'd like to keep it safe and secured.

I have said this so often I'm gonna sound like a fan boy, but I like the Timbuk2 bags. I have used one daily for many years, and bought another just cause I wanted another. Plenty of sizes, styles and colors to choose from.

Classic Messenger Bag | Best Messenger Bags, Crossbody | Timbuk2 Bags

They come with a chest strap, which is mandatory for my ride.

I like the bag I have, as it mounts to my rack! It might be available elsewhere, but I got it via the kickstarter. The recommitting is easy, and it looks like a normal bag.

Water-resitant bike bag - Yak | CycleStyle Australia - Clothing & accessories for the stylish cyclist
* it fits a 15 in macbook no problem.