I know it lets you steal clothes and leave everyone naked, but can you give someone you pickpocketed some armor or clothing? It would be funny seeing imperials wearing stormcloak armor for example

Yeah, you can. Whether or not they equip it immediately (or at all) depends on the person, I think? But it can definitely be done.

Thats cool, now I think I will work on my pickpocketing.

It's pretty easy to level, so that shouldn't be a problem. It just takes time and patience.

It just takes many quicksaves and many quickloads

I thought about mentioning that, but it's a bit too much like an exploit for some people, so I figured I'd leave it out~

I've tried sticking execution hoods in peoples inventories to see if they will wear them and it never gets equipped. Kind of a bummer really, tho you can get your followers to wear the hoods.

A little off-topic but your post (tc) reminded me of the days in morrowind where you would sell armor and weapons to vendors in morrowind, and instead of them making it available to buy back, they simply just equip them lol

Lol. Oh, yeah. That's very funny. They liked to sample the fine merchandise.