Without going too far afield from your original idea, why not elevate your game a bit and bake a
tarte tatin? Improve the garnish a bit by serving it with a cold, hand made
creme-anglaise -- which is pretty much the same thing as melted French vanilla ice cream, but better.
By the way, it's usually not a good idea to garnish a pie with a cookie, becuase the cookie detracts from the pie-crust, and vice versa; and when it comes to a tuille sharing a plate with an old-fashioned, home style apple pie, egregiously so.
FWIW, if you do go pie, I recently posted instructions on how to make a very flaky crust:
pie bakeoff.
The basic proportions for pie dough are are 1/3 cup fat (all lard is best, but you can use shortening and/or butter), 2 tsp sugar, 1/3 tsp salt (about), pinch of baking soda, and 1 tbs ice water (about), for each cup of flour. It's worth memorizing. It's also a little too generic and spartan for my tastes. I actually use a generous 2-1/2 cups and treat the other ingredients (except the water) as though I were using 3 cups of flour -- in short, tripling them.
Cut the sugar in half, use all butter instead of lard or shortening, and you've got a
pate brisee, suitable for any tart shell.
Alternatively, make a
pate sucree, or
pasta frolla.
BDL