J.D. mentioned being all packratty about his clothes. I have the same problem with 'em (possibly even worse, because I'm a nonstandard size and at one point most of my clothes simply didn't fit). I had to set up a Project to go through my clothes and retire those that need to be retired. I'm still working on it. Some mental tricks that are not strictly necessary, but help me:

1. If you have a lot of hanging clothes, an extra rack might help give you enough space to organize, especially if you organize visually.

2. If you make up mental parameters for a wardrobe (I need this many suits, this many dress shirts, this many jeans; everything must fit and be in good repair; my dark neutral clothes should all be black/brown/navy; I prefer natural fibers/no ironing/machine wash/whatever) it might be easier to send clothes that do not match the criteria to pasture.

3. It may or may not be fair and s/he may or may not be willing, but you could try asking your partner (if you have one who notices) to put stuff you ought to get rid of aside for you to evaluate later with that in mind. If all the bad clothes secretly migrate elsewhere, you may not even notice and find it easier to get rid of when you finally get to it. Not something I can do, but it would probably work if I could.

4. Find someone (tailor, neighborhood teen, whatever) you can pay to mend clothes that are almost ok (just a missing button, or loose lining/hem, or it needs a patch that won't be a big deal). While it would be cheaper to do it yourself, I find that when I have Issues about things it helps to outsource them. And knowing that things that are almost in good repair can be kept can help with getting rid of those in truly bad repair.

Any other ideas? I do not actually recommend what has helped most, which was a basement flood that meant I had to redo most of my laundry at once (and I threw in the rest for good measure).

what helps me - I'm always purging.
It isnt just a now-and-then big project.

At any time, when I see/feel the need I dump an item into a donation box I keep in the closet.
It gets full to a certain point, I take it to the consignment shop or salvation army.
I also always have a box going of "havent made up my mind yet" and "mend/alter before wearing again."

I find this works better for me than those huge purge sessions. Big job into small tasks doesnt hurt my brain or my attachment issues

I do a twice-a-year assessment. At the end of the winter, I go through my winter clothes and if there's anything there I didn't wear during the winter it goes to goodwill. Same thing at the end of summer: whatever I didn't wear during that summer goes out the door.

Nothing except food, investments, and organizational supplies gets bought in my house without two things going out. It is one thing, for me, to say, "Can I afford this red dress?" and quite another to say, "What will I have to give up in order to buy this red dress? Is it worth it?"

I'm with Frantic and Laurah.
I'm getting less attached to my stuff than I used to, but I always have to think about getting rid of my clothes. Most of the time I see the light: why a sweater in this color? why these T-shirts bought on-line which I don't even like?? why those pants which only remind me of how bad I used to look??? Declutter!
Thank God I'm becoming a wiser shopper and don't need to get rid of so much clothes anymore.

A trick that I have read in multiple place is to turn all of the hangers in your closet backward. Once you have worn and washed/dry cleaned an item put it back in the the hanger facing the proper direction. After each season donate any items that are not facing the proper direction. Obviously if you start this project now and own a heavy winter wool suit you do not have to get rid of it by the end of spring if it has not been worn, but if you have not worn it by the end of next winter, out it goes. Your wardrobe will be cut down immensely within one years time.

Check out the book "Dressing Well" by Mary Lou Andre from your library. In addition to its fashion advice (some seems geared to older women, just mentally adjust based on your age) it contains a chapter on reorganizing your closet. Very helpful.

And don't forget, you might be able to sell some of the clothing at a consignment shop. Whatever they won't take, donate to goodwill and get a receipt so you can claim the donation on your 2008 taxes!

knikki, I use the "backwards hanger" method and it works wonders. I always know which clothes can be safely donated to charity (or taken to consignment if they're in top shape) at the end of every season.

My goal has been to narrow my wardrobe down to the things I wear and need, so I have fewer clothes. This saves me time and money at the laundry. Think about it - fewer clothes = fewer loads to wash = less water used, less electricity used, less money spent!

My weight usually stays within a 10 pound range, but I can wear clothes size 8 to 14 in that range. Rather than get rid of wardrobe basics that never go out of style, I've packed a few boxes with those clothes that don't quite fit at the moment. Whenever I lose 5 pounds, I tell myself that I need to go at least 2 years at the lower end of my weight before throwing those clothes out. Sure enough, I always seem to have a small, seasonal weight gain around the holidays. Accepting this about myself has saved me lots of money, and I'm not donating nearly new clothes any more.

I couldn't give you good advice. I either dress like a homeless person, or a stock-broker.

Ha! I love that. As a 26 year old full time grad student as well as full time professional, you described me perfectly!

I've read that one too, but I use a slight variation; turning all the clothes hangers around to start is a steep 'start up cost.' (or at least seems inconvenient)

All of my clothes are on a single rail, pants on the right, shirts on the left. After I wear a set of clothes (guys don't have 'outfits' ), I put them in the middle, between the set that I would have worn yesterday. After a while, the clothes that I don't wear often work their way to the outer edges. It also makes it easy to tell how recently I wore something, so I avoid wearing the same thing to often, or two days in a row!

If you have the time, trying on every single piece of clothing while you declutter can really help (esp. if you have a good friend or SO to help with their opinions!) A lot easier to sort things into 'definitely don't want anymore' 'rediscovering cute clothes you'd forgotten about' and 'wear often'. The stuff in the second category can be placed into a purgatory... but don't let it become a bigger pile than the first one!

We live in a historic house and as such, due to a tiny amount of closet space, each new clothing/shoe purchase generally has to be matched by a clothing/shoe donation.

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