How do You go about or decide what to toss/give away/dispose of aka simply 'get out of your closet and life' when it comes to your clothing?
I spent 15 years becoming ill and thus from it FAT! As I got more ill, the clothes kept getting larger. Finally transplanted and fit again, now I can wear what I wore BC- LOL Before Children, what did you think? So, for the last couple years a new item here and there was about all I purchased, finding it too much fun to slip back in the pee-wee sizes of yesteryear....now, (due to exercise) some fit some don't, most all are outdated & I'm up dating my new wordrobe with my 'new size' cuties.
Problem is, what to keep and what to dismss, dare I hang onto a few favs from all my previous sizes, just in case illness strikes again or a few favs from yesteryear in the hope that they come back in style. Jeans OK, jeans are jeans..at least the 30 year old pairs go up to the waist! LOL Are there any Great organizational wizardettes out there with a sure fire way to cope with this daunting task?

Go with the 6 month rule... if you haven't used it in 6 months (maybe make it 18 as a consideration to seasons), get rid of it... but, keep the age-old standards, i.e. a wool coat, black skirt that could be altered if need be
If you keep the bigger items, they may call your name, giving you license to grow back into them.

I have three sizes in my closet...and sad to say I wear them on a rotating basis. Yuck...but I'm glad I haven't thrown the different sizes away. If you have the room, I'd keep them.

Throw or give the ones that make you feel like a loser when you see them away and be comfortable. You have most likely earned the priviledge. I got rid of all my ridiculously skinny clothes long ago. If by some miracle I would become thinner again, I would deserve all "new" skinny clothes anyway, that my take on this question...

You can do what I do. I go through my closets once a year and weed out
anything I have not worn in a long time. Goodwill loves it!

To me, keeping the "big" clothes is giving yourself permission to get big again. Why not? You have clothes to wear if you do. I would toss them in a heartbeat.

Throw away every single item that reminds you of what you used to be. Then start hunting for bargins and begin a new wardrobe for the new you. You deserve it girl.

By the way, jeans DO go out of style. You might consider buying new ones??????

Great advice! I've also been doing the great 2008 clean-out and have been faced with similar thoughts regarding the closet. I'm dumping everything that's unlikely to ever leave the closet. I was shocked at the things I've been saving, knowing full well I'd never wear them again. I, too, have a few sizes represented there and am getting rid of everything that I can't wear today.

WOW Thanks Ladies,
After reading your great ideas it seems from each of you I got a good idea, plus the motivation to actually "Get'er Done!" LOL
MY personalized plan from combining everything mentioned here is to:
Buy New Skinny Stuff, already had that in progress..I try to pickup at least one bargain everytime I go shopping. Size isn't my only ligit excuse, my new job requires business casual dressing.
Of the BIG stuff, since in reality (Health Reasons) I could start retaining fluids again at the drop of a hat, I'm keeping a few of the expensive & a few of the ultra comfortable lounge wear items ~ Bagged way in the back forgotten unless needed.
My really favs (that stand the test of time -like my black cardigan type jacket) of the big stuff I'm going to have altered..hence NO going back on purpose to the larger sizes.
TOssing ALL Looser clothes! Like the Wally world knit slacks with elastic waist bought cause that was all I could stand on my big me. LOL Not funny but at oe point I looked like a pregnant mid 40's fool!
The old jeans, keep for yard work and on the ranch riding etc..BUY more new styled jeans, I have several already, but may as well go whole hog and get a few more.

**OF what fits that I'm not wearing, TOSS!
All tossed stuff is going to the 'Doggie Store', it's a Thrift Store run by our local animal shelter and all profits go to help with care of the homeless animals..it's a No Kill Shelter so they really need it.
Ready Set GO! Thanks Gals, I'm going to go round up boxes & get in gear. Ya'll are the best motivators on Earth....

Start from the skin out and buy nice undergarments.also less is more..mix and match..
I gave teaching clothes to a friend who was still working so that made space.
I have classics..will keep hold of them .
I have more casual wear but wish it looked smarter..so I keep a quest for loose bottoms that dont look like jogging pants..That also have matching seperates.so any advice.
Then if someone calls I can look like I have taken care without looking as if I have been to the gym.

Mountain ash