If you sell them in a lot on Craigslist, or individually, you can make more money. If they're nice, you should definitely take that route. That's what I'm planning on doing. I too have a LOT of nice, cute clothes. Like, an entire wardrobe of cute brand name stuff.
You should try borrowing a manikin from someone and putting the clothes together in cute outflits, and cliping the back a little so it has a nice shape before photographing. Take pics of EVERYTHING like that, and keep them in outfits, and you can make a buttload of money for your clothes. People are way more likely to buy your stuff if they see it in an outfit form like that. You're not going to make a lot of money though, be reasonable aout the price. No matter how nice the stuff is or how much you paid for it, it's still used. Keep that in mind.
Anyway, as of late I gave most of my stuff away to Goodwill. But I didn't dress cute when I was bigger. At my biggest, I wore pretty much black t-shirts and jeans, so yeah. But now I'm starting to sell stuff.