Sword and Shield bring so many cool quality of life and UI improvements, but somehow, the UI around held items, and only the UI around held items, just makes no sense at all. Let’s break it down:
In the context menu when you select a Pokémon on the party Pokémon menu, there’s a “Held item” option. The options under that (assuming the Pokémon is currently holding an item) are “Open your Bag”, “Put it back to your Bag” and “Give an item”.
“Open your Bag” will open the bag, so that you can give an item to the Pokémon...
...except that when you select an item there, the top option will actually be “Use this item”, which will use the item instead - even though you entered the bag specifically through a “Held item” option.
The other option is “Give to a Pokémon”, as if it’s going to let you select a different Pokémon to give it to, but no, it’ll give the item to the Pokémon you selected previously.
“Put it back to your Bag” at least works as you’d expect, but is it just me or is it pretty weirdly phrased? Shouldn’t it be “Put it back into your Bag” or even “Put it back in your Bag”? I’m not a native speaker but it sounds off.
The “Give an item” option, on the other hand, is for moving the item to a different Pokémon in your party. What?? How on earth is that “Give an item”?
(While in the party menu, you can also press X to “Swap held items”, in order to move items between your party Pokémon. Why is that bizarre “Give an item” option even there when there’s a much more sensible way to do what it actually does.)
Meanwhile, when you select a Pokémon in the box, the only held item-related option in the menu will be “Check held item”. Sounds like an option to see if the Pokémon is holding an item and if so what it is, right? Maybe it’ll tell you what it’s holding and then give you some options?
But! Actually! If your Pokémon is not holding anything, this option will just go straight into your bag to prompt you to give an item to the Pokémon! (Same “Give to a Pokémon” option, but this time there’s no “Use this item”.)
Meanwhile, if your Pokémon is holding something, the “Check held item” option will ask you to confirm that you want to remove the item from the Pokémon. I never said I wanted to remove it! I picked an option to check it!
Also this means that the UIs for held items are just arbitrarily completely different depending on whether you’re in the party menu or the box, including how if you’re in the box there is just no option to immediately give a new item to a Pokémon that’s already holding one, without first removing the current item.
It took me a while of gameplay to get any sense of what any of the item-related options actually meant. The first time I was going to do something with held items I just ended up being completely confused and felt like I eventually stumbled into doing what I wanted basically by accident.
I’m guessing these are probably largely translation mistakes. The “Give to a Pokémon” option, for instance, is just phrased in a way that would make sense in one context where that menu is used but not it another, which would almost definitely be the same in Japanese with the lack of articles, and I can picture these various other phrasings as being ambiguous in Japanese, one way or another. And then... probably the playtesters for the English localization were just not much for held items and never actually used these options, and thus didn’t notice. It’s really glaring in a game where the UI is otherwise so polished.