Nicole, I do remember that dress - I wasn't so keen when you first posted it, even if it fit well, the color was one I personally steer clear of (too much like a sweatshirt color). But, I think with the black tights, black boots, the cardi and the cami it looks AWESOME! This is testament to your imagination and taking a piece others might not see the promise in, and making it work!
As for the belt, don't ask me... listen to Angie! I am not a huge belt person myself, I'm in the learning curve just a few baby steps ahead of you. I do think you should keep trying though. I am learning from Angie's advice right along with you.
The futzing thing still gives me pause too - if you read the comments on the Lucky site, a lot of people complain about belts for the office being too fussy. However, I'm not ready to give up and I hope you don't give up yet either.
I have a hunch the futzing can be minimized with a looser, smaller belt. And maybe also just getting used to wearing one?