Simply put, they are learning, exploring, reasoning, expanding, etc. I couldn't say that I did that when I was younger (I wouldn't be able to remember haha), but I'm sure I did similar things. You might want to ask him why? See what kind of answer he gives you and then reason with him! I'm sure that that will get him brain moving. lol
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That's funny. My 3-year-old little boy also does the same thing. There's always a trail of clothes going down the hallway to his room. Sometimes he doesn't want to wear anything at all and just runs around in his diaper. So it must be something with that age. They are trying to be independent, and maybe this is a way that helps that feel that way.
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My kids have all done this. They do it for a few months, and then they're over it.

I really think that they experiment to see if looking different changes anything inside. And I also think they're practicing the skill of taking things off/putting them on, and the choice makes them feel more grown-up. Because just a few months before, an adult picked everything they wore and put it on them and took it off again.

If you want to make this urge constructive, give them a rag and an environmentally-friendly cleaner and get them washing walls and your baseboards. :-) Or get them a small pitcher, fill it with what you want them to drink, and put it on the lowest shelf of the fridge. And then keep paper towels where they can reach them, and at the first spill, help them clean it up, and keep helping until they realize they need to clean up their own spills. Makes them feel REALLY big!
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