Oh yeah, I can totally relate to this story...
A long time ago... There was this happy hippy used clothing store type place. You could sell your old clothes there and then buy even older clothes... that smelled like incense... (I was never able to make any sense of it but I can see the trend has continued to this day.) Sometimes college kids would buy used clothes there so they could look poor on the weekends... For I don't know what reason....
It's far easier and cheaper to just be poor and then your clothes kinda take on "the look" of being poor all on their own... However, I have been informed that IT JUST DOESN'T WORK THAT WAY!! For some inexplicable reason if you wear clothes until they are falling off of you, you are a bum, BUT if you buy clothes that homeless people sell in the spring because they don't want to carry them around all summer, they magically become VINTAGE, which means they have monetary value and are also suddenly socially acceptable.
Anywhooo... At the time, I couldn't afford to actually shop there but sometimes I would go hang out there while my friends sold clothing they stole from houses their girlfriends were babysitting for. The old hippy guy that ran the store was interesting to talk to as he tried desperately to explain away this capitalistic endeavor by pointing out his charity work. Which consisted mostly of an old wooden box out front which had free clothes in it which for one reason or another could not be transformed by whatever magical process the other clothes that became vintage went through.
And obviously even without any signage the box of clothes is for poor people as the clothes inside are not worth so much as one nickel in the used clothes store. These are clothes that no one is going to buy ever. They are sometimes damaged beyond repair.
and so, One fall evening, since I was poor and homeless and lived under a bridge and slept on concrete and winter came unexpectedly early that year and I woke up in the middle of the night from the pain of freezing to death, obviously I was qualified and in strict adherence to all of the delicate unwritten laws that govern the box of free clothes outside the happy hippy clothing store and their use.
I still had that buyers remorse thing you were talking about and felt bad taking some clothes on that frigid night and wearing them over top of the clothes I had on because even in the condition I was in, certainly somewhere on this god forsaken planet there was someone else who needed and deserved the clothes even more than I did.
BUT I FOUND A CURE!!! And the cure, for the buyers remorse we are feeling, is pretty simple, you go donate some clothes you are no longer using and it makes you feel a little bit better about taking the free clothes out of the poor box or that situation you were talking about.
Because unfortunately no matter where you live or what time of year it is somewhere there is a man or woman that could really use that item of clothing you are no longer using even if it doesn't fit right and all they end up using it for is as a pillow to keep bugs our of their ears, it is totally worth it.
And the most critical, crucial and important part is you do not for any reason give any article of clothing to any homeless person directly. Just put it in the box!
What I learned is that is that the free clothes box operates on the same magical principle that turns crappy clothes into vintage merchandise.. so if someone is not deserving enough for whatever reason when they open the free clothes box it appears to be empty.
Also, Through no fault of your own you can very easily be mistaken by homeless people for a ravenous vermicious knid and dispatched with the shank of unspeakable jagged rustiness. On the plus side you will probably die before the tetanus kicks in. All praise, glory and honor to the box, amen.