I like the velcro idea. I understand what you all are saying about him learning how to sew. I have shown him how to sew on my machine (he worked on a school project using it). I haven't shown him much with hand sewing. I really wish sewing the patches had been part of something he'd learned as a cub. I will admit, though, that sewing these patches by hand isn't something I'd look forward to because of that plastic backing (I'm with you, SSScout). If we don't go the velcro route, I'll try to have him (and me) do the loop around the edges. It's frustrating to me that kids don't have anyplace where they learn basic things like cooking and sewing (not cooking outdoors) like we did in home ec. I know that is something we can teach at home but with all of the activities they are involved in, time is an issue. There might just be a sewing and cooking class at my house this summer.
With the plastic holders, I was looking for a temporary, easy way out. Velcro might just be that until I can get him on the sewing bandwagon.
We bought him the microfiber shirt and it has the button pockets on the left as well as the right. I don't know if these are new or not.