You won't be sending in any documentation of the cost basis for donated items, but they should be retained for your records.
The Form 8283 will be completed automatically when you enter the non-cash donation over $500. Date of contribution, date acquired (various), how you acquired the items (usually purchased), the cost basis, fair market value, and method used to determine fair market value.
You will have to estimate the cost basis if you don't have the receipts. Any reasonable method will do. Thrift store values can represent approx. 10-30% of the original cost of items usually. Enter under the Deductions & Credits, Charitable Donations and import from ItsDeductible.
See below for reference.
https://ttlc.intuit.com/questions/3944751-donations-of-household-items-and-clothing-over-500-on-one-...
https://ttlc.intuit.com/questions/2683553-what-to-do-about-clothing-donations-over-500-without-recie...
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