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How long is to long to hold on to clothes that don't fit? Is there really any point? I am working out with the trainer and will get down from were I am now but Lets say 4-5 sizes from where I am now? I have this pipe dream and feel like I am wasting space in my drawers and closet when I really don't have the space. Whos to say my body will be shaped the same as I was before... Any insite will be helpful!
Re: Downsizing The Closet
My weight has always fluctuated and I'm always holding onto clothes that don't fit. I try to go through the closets and drawers at the very least once every two years, I just did it recently after a stretch of probably 3-4 years and got rid of like 3 trash bags of clothes.
I've found that even if I lose the weight that I usually want new clothes. Now I hold on to a few favorites but get rid of the rest.
Even if my weight fluctuates a bit, I get rid of clothes on a regular basis. I agree about buying new clothes later on if I need that size again. I try to go through once a year, but at least once every two. If I haven't worn it in a year and/or it doesn't fit, I will pass it along to Goodwill. Things that I like but need mending or altering, get sent to the tailors. Things that I "rediscover" get put in the front of the closet or drawer. I figure that if I didn't get it worn in that amount of time due to size or lack of interest, it's time to pass it on to someone who will. The exceptions are formal wear and such (ski coats, etc).
The best thing is that once I clear things out, I can see what it is that I love to wear and what additional things I might need. I usually go shopping following a clean out to reward myself and fill in any gaps.
Don't forget to accurately estimate what amount you have donated to charity. It is tax-deductible and I find that I always underestimate the value. Right before we moved, we donated more than $1000 worth of clothes once we thought about it (coats, suits, shoes, etc that we all worth more than we thought). I think SA has a give for what to estimate for each item. Now we count out what's going in each bag to make it easier.
I don't have a lot of clothes. I never was a shopper and my clothes from way back then mostly fit, except one or two pieces that can't get on me anymore. I am almost ashamed to admit that I have old clothes like over 8 years old that I still wear.
I stop wearing my clothes when they get permanent stains, they rip beyond repair etc. Then - and usually only then - I go buy something to replace it. I really need to change that and shop for nice things for myself more. Come to think of it, the shirt I am wearing today is like 8 years old and the skirt about 6 years. Jeez! 
Anyhoo, back to OP, I would say, get the new clothes for your new size! By spending the money on the new clothes, that would motivate me to remain that size to avoid buying, bigger sizes in any near future. LOL go for it and clear the closets!
Our New Home! Renovation Underway! The Law Nest
TTC Journey
7/2008 - begin TTC
7/2009 - began charting
9/2009 - Dx Endometriosis
10/2009 - HSG/SA (Normal)
12/2009 -6/2010 - Lupron #1 & 2
Sep-Nov 2010- Clomid Cycles #1&2 = BFN
Dec 2010 - Clomid Cycle #3 = BFP (1/11/11);no h/b (2/10/11); D&C (2/23/11)
5/11-6/11 - herbal tea regime = BFN
7/24/2011- herbal tea regime = surprise BFP
totally agree. I use itsdeductible.com to keep track of any donations we make and they make it really easy to figure out a donation total for clothes, as long as you have a count.