Do I need to list every single item on a charitable donation (example: 2 shirts, 2 pants, 1 dress, etc) or can I just put "clothes" and an estimated value?

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No, you do not need to inventory every single item that was donated to charity. Especially for small-dollar value items, reasonable groupings of items and your best attempt at fair market value (FMV) will be sufficient. If you were provided with receipts for your donations, even if they only contain broad groupings of items, keep those receipts with your tax records to substantiate your deductions.