I am pretty bad ass with the jacket, especially considering it's an Eastman Leather G-1. Ok, at least the jacket is bad ass. I don't find my khaki shoes to be uncomfortable. I'd actually rather have leather soles than the Bates rubber ones.
But do I neeeed to buy an NWU?
Legally? It's part of the sea-bag, so I guess the answer is yes....
But, I would say it all depends on where you are and if you unit wears them. Since you're at Maxwell, I'm assuming your don't need them.
What's your next duty station? That will determine what uniform you need.
If you're going to a Joint command, you may get issued the Type II or DCU's depending on the AOR you are going to work in. Of course the senior Navy guy at the command may decide that you'll wear NWU's or may allow flight suits. (JFCOM it was left up to the Directorates. I worked for a shoe, so I got to wear khakis. Others got to wear bags....)
If you come back to the Navy, since they replaced wash khakis, you'll need them if you are going to a ship? (Or a squadron that deploys on a ship).
Each staff will be a little different. Ashore you can always wear khakis since they are a step-up on NWU's.