I stole an X-01 head form a shop keeper(I won't spoil it fr you). But I picked it put and let it float in front of me until I got far away. Then a through it down two flights of stairs and then put it in my inventory. My question is.......... Can I wear this armor in front of the shop keep now with being penalized?

I have a stolen T-45 suit and while settlers make comments, no one has attacked me or anything.

If you are not caught picking it up its safe. Think you can even sell it back but not relevant here.

That exploit has been around since morrowind. There are bugs in this game older than the players.