I have made lots of costumes that require quick changes and often add zippers to a faux front. For example, when making Shakespearian gowns, all the lacing and eyelets are permanent, where as I place a hidden zipper underneath to enable to actress to change quickly. This may be an option for the dress shirts. I would try a faux button front with snaps sewn underneath, unless your grandson likes the look of western wear, where snaps are the norm.
As for the Tees, Duluth is a wonderful place for long tails. I highly recommend it.
Best of luck to you.
North Central, PA
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