Thankfully, I'm going through this too. I say thankfully because I need to remind myself not to worry about the expense of replacing my whole wardrobe.
I had carted around tubs and tubs of smaller size clothes for years and finally got rid of all of it. Now ............... well, now I scrounge around for something that looks halfway decent.
I went to Ross and Bealls and got a few tops a couple weeks ago and I cycle through them over and over again. I have some pants that aren't TOO baggy and some that are a little too snug - so depending on the comfort factor for the day I pick amongst those. But I'm on the verge of needing to buy smaller stuff. And I hate to be spending money on transitional clothes, but I don't really have a choice.
While I'm extremely grateful to need smaller clothes, it's also becoming a bit of a budget buster to keep reoutfitting myself. (even just a few pieces at a time.) I get to worrying about it every now and again, and usually decide that it's a good problem to have, and I should just smile and hand over the credit card.
IT will be VERY NICE to get to my goal size and be able to splurge knowing that what I buy will last me a long time. And it's really nice to get some cute stuff for a change instead of the plain jane tshirts I've worn for years and years.
I actually had a pair of OLD size 18 Lee jeans stuffed back in the closet that I wore out last Friday. Haven't worn those in probably 10 years. Talk about ego-booster!