Super Cloudbuilt

While you could get this fairly early on, I recommend holding of on this one until later in the game for two reasons.

1: You will most likely need items on the harder levels, especially the Skull Rated ones and it’s better to wait than having to farm them later on.
2: You need to be holding onto 20 items for another trophy.

What you could do if you want to get this early, is backing up your save, activating a bunch of items, unlocking both the 2 items and 7 items active item trophies, then closing the game and reloading your save.

You obtain items from bringing all 4 Item Keys to the end of a level and by clearing Will-O'-The-Wisp challenges in Story Mode, after which you can claim your new items from the lockers at the finish line.