The best gift in love is the gift where the giver considers specifically the person they are giving to. We know that our gift is well received when the person responds, “How did you know?” It shows our care and respect for the other person when a gift is specifically suited to their needs and wants.
This is the same for the poor. If a person is homeless, you want to think about their situation and give something that is suited for their situation. A pair of socks is more welcome for most people on the street than a four person tent (where in the city would someone put up a four person tent?). A mentally ill person might appreciate a video rather than a book of crosswords (although, I know a couple mentally ill people who love crosswords, so you don’t always know). A street person wouldn’t have anywhere to plug in an electric razor, but they could really use a nice blade razor with a pack of fresh blades.
We just need to think ahead and make the gift suitable for the person’s situation and need. This is why it is often good to ask before we give, if it is possible.