Oh hunny I feel your pain!
Have you tried op shops (well thats what we call them here, maybe thrift shops over there?!). You would be surprised at what you can find.

I had to bite the bullet and get a loan out to buy some new clothes. I felt I deserved it but now they're already getting too big and it feels like such a waste.

Maybe sell your clothes on Ebay or something and buy yourself a couple of new things with the profit?

I prioritize replacing pants because they are the most obvious when they don't fit right. I safety pin my skirts and use sashes or belts to cinch in shirts and dresses. It doesn't work with everything but it can help extend a few items.

I'm starting to have that problem. I still have some stuff from what I was smaller I'll be able to wear, but after that I'm out.

Even now the only jeans I have are my bigger jeans. They literally fall off. But I can't spend any money on clothes right now (student) and so I just got a nice belt and strap 'em on. Not always pretty, but I can't do anything else right now.

Around here there's a sunday market where you pay $20 to get a stall, and heaps of people use those to sell their old clothes, and plus size clothes usually sell very well

if there's a similar type market in your area maybe you could try the same, and use the profites to buy new clothes ^.^

I agree with a bunch of posters, thrift stores and flea markets are awesome for getting new clothes. you can drop off your stuff that's too large and go on a spree for cheap clothes that fit properly.
you can put a little bit of money aside each time you loose 5Lbs, then when you reach your goal weight you will have a nice chunk to buy a new wardrobe.

Thrift stores! I can't say enough about how awesome thrift stores are. Name brands, great prices, and tons of different cuts so you're almost guaranteed to find something that's right for your body.

I recently bagged up all my too-big summer clothes, and when I went to try on my autumn/winter clothes, I discovered none of those fit either. It was time to go shopping or go naked. Two thrift stores and about $50 and I have a whole new wardrobe that will hopefully last me through most of the winter. (My major score was four pairs of corduroys that are like new, fit me like a dream (low rise, boot cut), and are name brands - for $3 each! And cords are versatile enough for office wear or casual wear.)


ETA: Like caryesings, I don't belong in the 20-somethings. But it's a universal issue!