What to wear when you hate the way you look?

I have lots of clothes that I like.  Unfortunately, I don't think many of them fit me right now.  Due to a certain medication that had a nasty side-effect of rapid weight gain, I'm now 2 sizes larger than I was 1 1/2 years ago.  So I don't feel like I look good in anything.  But I enjoy fashion!  I like to be stylish.  I want to wear some of my great clothes again.  So I'm going to do some experimenting and see if there's any way I can still look great in some of my old clothes.  I already know having make-up on helps tremendously - it gives my face dimension instead of looking like a big blob.
Now I'm going to try some outfits, and if I come up with successful looks, I'll post pics of them.  If not, you'll see nothing!   Experimenting to come....