if you reverse pickpocket some one and give them some thing like new armor/weapons, like a town guard will they use it?

i would always in Oblivion change up the guards armor on them in every town just to make them more bad ass looking and every thing.

its still some thing i like to do, can it be done in Skyrim?

Unfortunately not.

They will use the weapons, but they will not don any armor. Even if you get them naked. They will remain naked for the rest of the game.

I don't know about guards, but I know it won't work on a wife. They just continue to wear their same boring outfits.

No it doesn't seem to work that way, I think the item just sits in their pocket.