My vote is to keep what you love, and toss the rest.

When I started gaining weight back, I tossed most of my skinny clothes that I didn't love. The stuff I still have is a pair of size 11 jeans, some size 9 goth pants (Hey, I was darn proud of those...these were bought after my doc told me I could lose all the weight I wanted, but I'd never get a single digit size over my hips ), and a green size 12 formal gown.

Everything else went the way of the dinosaur. If I'd held on to everything, my closet would be overflowing. I am nothing if not a clothes horse.

Keep them all!

I kept my skinny clothes from back in 2005. My girlfriend kept telling me that I should give them away or sell them to a consignment shop since she didn't think I'd ever be able to fit them again.

I can fit almost all of them now and it feels like victory every day! BWAHAHA! I WIN! I shop for new clothes right in the comfort of my own closet. It will be such a rewarding feeling when you can do the same.

I love that you have 7 items of clothing wrapped in a belt that doesn't fit. Great Idea---- LOL, that is so me, and I love the way you worded that, very funny. That is great. See this is the stuff I love on here. =)~

I kept one suit that fit for maybe a month (size 6). One dress (size S). Some lingerie (I can dream can't I?)
The rest went to Goodwill and the Women's shelter resale shop. I figured that I would deserve a shopping spree if I ever got back down to that weight.

Fast forward to 7 years later:
Since I kept almost nothing - I have been to Goodwill shopping for "in-between" clothes the last month. NOTHING fits anymore. While this is awesome, my work wardrobe is dwindling to a bunch of oversize clothes that really do not fit. What a wonderful problem to have!!!

I say keep it all, but I am a HUGE packrat. I have every pair of jeans I've owned since 10th grade that weren't falling apart. My pants range from 14-24, and it is my goal to one day be able to throw away that one size 14 because it's too big. I also have a lot of shirts hanging around, too. Mostly of my shirts back in the day were t-shirts, and most fit me now anyway, but I do have several "nice" shirts that are too small. I hope to toss them one day because they are too big as well.