Putting on a none would be tricky?

What does that mean?
For example, if you check your jeans and hit “a” button.

When wearing something and the pressing the wear or activate button on it (activate is the same as wear for clothes) is says putting on a none would be tricky.

Activating clothing is a synonym for 'W’earing it. But if you’re already wearing it, you can’t put it on again.

What’s happening is that the inventory is a different list from the worn items list, so it tries to 'W’ear an item that doesn’t exist in your inventory – thus, it’s a “none”. And putting on a none would be tricky.