+1 on hush puppies. Silly name, but incredibly comfortable. Spring the extra few bucks for a comfy pair of shoes. I went cheap with some Deer Stags once, and I was miserable. Very tough leather.

For a bag, I've had good luck with this Timbuk2 bag (size small). Very high quality. TSA-friendly for your laptop, slides onto your suitcase handle, plenty of space without being too bulky, and a rational number of pockets for organizing without going overboard. It's on Amazon Prime. Also completely usable for non-work purposes.