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Goodwill: Great for any style of clothing. Just drive up and get your tax receipt. You fill it in later.
Salvation Army: Great for any style of clothing as well. However, they will make you fill out the receipt right there stating what you dropped off. So if you are in a rush, then go to Goodwill instead.
Battered women's shelter: Only works if you have women's or children's clothing. They typically use the clothing for jobs and such, so it needs to be in really good shape and current.
Homeless shelters: Will take anything. Not sure if they give out tax receipts though.
I take everything to Goodwill. It's convenient, quick, and easy for tax purposes.
As for the random donation boxes, I know that at least in Syracuse, NY, they work fine. My friend interned with a homeless shelter there and they had her spend a few days with the pickup guy...the group also ran a store. Anyway, if you don't recognize the group who's responsible for those, then stick with the others.
When I have a few minutes, I run TaxCut's "It's Deductible", which comes with their tax software. You choose the item of clothing from the drop-down list, and it gives you some suggested values. In 10 minutes, you can easily itemize 20 pieces of clothing by looking at the picture you printed. Then print out the list.
Save the Goodwill receipt, the picture and the itemized list for tax time. This is the kind of documentation the IRS cannot argue with. And with TaxCut, you end up getting far more than just estimating the value of the bag of clothes.
Thanks for highlighting my "top bloggers" post. It seems to have piqued the interest of many! :)