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Mercy Boucoup on wells at in old town. A clothing resale shop where proceeds benefit a local charity. They take clothing in good shape from nice and high end brands
Bottomless Closet, welcomes the kinds & types of clothes women need to get back to work after being unhoused. They are located in downtown Chicago!
Mt. Sinai Resale is a very nice thrift store up in Lakeview, and they have a separate section of their store for designer and higher end clothing. Proceeds fund cancer research at Mt. Sinai Hospital as well!
Sell it
the amount of money you can sell these clothes on poshmark is not worth the amount of time you have to put into selling them. I know because I tried! A $170 aritzia dress won’t even sell for $20
I don’t have a specific place in Chicago for you but when I used to live in LA, there was a local org that took nicer clothes so foster kids could choose / “shop” there for interviews. I bet there are a few places like that locally, hopefully someone can help!
I post on freecycle groups
Could you work with a couple of other colleagues to organize a clothing swap at work? My office just did this and it went over well, and we donated everything that was left at the end was donated to a non-profit.
Brown Elephant!