Eze 18 vs 7

if a man does not oppress anyone, but restores to the debtor his pledge, does not commit robbery, but gives his bread to the hungry and covers the naked with clothing,

Clothing is a symbol of our human dignity. It is one of the things that set us apart from animals. And it’s within our fallen human nature to think that people with nicer clothing are somehow more dignified (even though it’s untrue).
So in thinking that clothing we would never be caught dead in, and would never want our friends caught dead in, is “good enough” for the poor, we might be unconsciously feeding into the idea that they have less dignity than we do. Although I think that even our “castaway” clothing should be donated rather than thrown away as long as it is still wearable (because ugly or old clothing is better than nothing), I agree with the idea that we should strive to think of “the least of these” as worthy of everything of which we believe we ourselves to be worthy.
We should think of ways we can clothe the naked with clothing that sends the message that they have dignity and are worthy of respect.