While waiting for DS to get up this morning I went through every stitch of clothing I own. If it was too big, it's gone. If I won't wear it for whatever reason, it's gone. If it had holes/stains, it's gone.
Part of this is a little scary. The if it's too big part. I have been here before, several times and I have always gained again. Sometimes I've had bigger clothes packed away, sometimes not, it hasn't mattered. But if feels good to clean out the too big stuff, and I know that if I do end up gaining again I will spend $ on stuff I don't like but that fits. It certainly isn't going to do me any good to hold on to the stuff and make it easier on myself to regain the weight. Anything that is in good condition will go to the building at our transfer station where you can leave things for other people to take.
So the fun part, was I unpacked my boxes of smaller clothes (I've always kept some when I've gained) and tried them all on. Most fit. Now mind you these are not "thin" clothes just "thinner". These are anywhere from 16s to 20s vs the 22s-26s I'd been wearing.
I still have 1 box of pants, mostly jeans that I can't fit into and 1 box of tops. And 1 box of seasonal that I don't know if they'll be too big/too small come the seasons (some Christmas tops and some summer clothes that are too tight right now).
But everything else I own I will wear and fits in my drawers/closet. No more overflow on top of the dressers. No more wearing stained/holey things around the house just b/c they are comfortable. I actually have comfy decent looking stuff that fits to wear around the house
I got rid of all but 3 pair of undies (they were too big) and bought new today. I also bought new socks for work, as my old ones were getting very worn out and mismatched. I also grabbed a package of men's tshirts and men's tanks b/c I like them for sleepwear. Even though that's all I bought new I feel like I have a whole new wardrobe! It feels great
I do realize though that the next time things get really too big (I'm guessing in another 20 pounds or so) I will have to buy new things, especially for work. But I am hoping by then to be in a close enough to "normal" size to have a wider range of places I can shop with big clearance racks. Clearance racks are my favorite place to shop

Kohl's and Fashion Bug here have pretty good plus size clearance racks, but I'd love to be able to shop the Old Navy clearance racks and places like TJMaxx too.
ETA: 1 weird thing I did: I kept 3 tshirts that are too big. One is the one in my avatar. My MIL bought them all for us a few years ago and it was too big when she bought it for me. Another is also 1 that she just recently bought for me. I kept them b/c I feel like I HAVE to wear them around her. Isn't that odd? The other is 1 that DH bought for me when work sent him to The Netherlands. I also kept 1 shirt that's way too big but soooo pretty and comfy and I just wasn't ready to give it away even though it swims on me. Weird the things we hold on to and the reasons why. Hopefully I will be ready to part with them all the next clean out round.