That is a wonderful thing, but does more than one person have the name ans will be gifting the child? Is it a homeless shelter where he is a resident (comes back to every night after school and living as if staying in a dorm) or a shelter where it is a bed/cot and they have to take all of their belongings with them everyday. I think THIS would be the deciding factor. If he is in a shelter where he is a resident, then card games such as uno, a little MP3 Player (you can get those cheap these days) with a gift card to get songs is a good idea. The shelters & libraries have computers to purchase songs. He then can have 'music' like his friends. If he is an 'overnight' shelter where he comes back just to sleep and must take everything with him during the day, then a 'hoodies, hats, gloves' are always a sure win with tween boys. You can even throw in some of those PJ pants. Now I am different from others here.... I do not feel you should get a load up from Good Will or a Thrift Store. At 12, he knows if it is something that is new/ with that new smell. He too wants something NEW to unwrap. Yes it is pratcial to think of going to Good Will will allow him to have more; but emotionally you would be giving a better gift by one or two things new than many things old. TRUST ME! Right now he is getting other 'hand me down/recycled items'; so new would be a gift in itself. I have done extensive work/volunteer opportunities in homeless shelters and many just can not understand the mind set of people in this situation. Trust me; ONE thing new means more than MULTIPLE things used. (Yes I know you can get new things at Good Will), but it is NOT the same. Homeless kids especially have said, it is so nice to get things still with tags attached and one kid I recall once being thankful to actual get something that was wrapped in tissue paper ;). I recall a mom/children combo onc writing that they dreamed of the time to sleep in a bed with 'matching sheets'. Something we NEVER think about. I know I am guilty. When I use to give sheets to the shelter, they were mix/match ones. Now I am sure to give matching ones and will even give 'kiddie sheets' so that there 6/7 year old girl can too sleep on matching Princess Sheets. (SMILE). I know that is a long explanation, but I wanted to use the opportunity to make others aware of this situation. That is why the donation of clothes (yes it clears our closet; but that donation is not the best donation for shelters); unless they are disposable diapers that our childrn have outgrown. In Wisconsin, coats, hats, gloves, boots are always needed.
So to your answer if it is a shelter where he return and is a resident; then something new and fun (MP3 player $10 these days) with music. (Uno Attack). If it is just an over-night shelter then new & pratical; Underwear/hoodie, socks/hoodie, hat/gloves & a hoodie sweatshirt or PJ pants/hoodie. I hop this helps. Thank you for doing this....