Christi - you're a doll! I think I was well trained by the women of my family
I only had pants in 2 sizes (about 1 year ago I finally donated the stuff from high school) so it's kind of been necessary. My next 3 pairs of jeans in the queue I found for around $13.50 apiece (cuffed capris on clearance from Old Navy - rolled down they were the perfect length for this shorty!).
Even with the tummy you can wear fitted things. Remember that deep v-necks, scoop necks, etc. will enhance your top and draw attention away from the belly monster. It's all a matter of making your boobs look bigger (yes, even if you're already chesty)!
Add a nice bra & you're all set.
Also remember to get versatile items. Like I said before, things that you could conceivably turn into something else (like top to tunic), as well as the kind of item. Those printed skirts are pretty, but not worth the price for the amount of time you'd be wearing them right now! But I always make sure I have some kind of outfit that's good to wear out on the town. I don't need to be stuck inside because I have nothing to wear!
Don't forget to check thrift stores (like Goodwill) if you have good ones!