For your boobs check out this subReddit. http://www.reddit.com/r/ABraThatFits/ There are other women there who are also going through weight loss and looking for advice there. Several of the members are bra fitters and can help you with bras that are good for your shape.

A properly fitting bra will improve your looks and self esteem. You sound a lot like me. Boob tissue does migrate and with good fitting bras you will be surprised at the changes you'll see.

If you're running you need a good fitting sports bra, too.