Expat Health Insurance
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Many of the second hand stores, at least in Prague, buy their clothes in bulk from abroad. Others, like specialist vintage stores, will buy older pieces of fashionable clothing.
The best thing you can do is ask store owners, especially in stores where they stock clothes similar to your style but don't expect to get too much for your clothes.
You can also donate your clothes to a place like The Prague Thriftstore, whose website you should be able to find on Google.
Good luck,
Xavier
Happy searching!
Xavier