I wore earrings for the first time in a long time.
Koichi has fun by secluding himself in his room and putting on masks from around the world every night.
Could you promise me that you will wear this good luck charm all the time, please?
Another verb for this kanji! Crazy! I know, I'm sorry. The previous ones were: 着る (to wear), 着く (to arrive), and now 着ける (to put on / to wear). At least it's similar to 着る, right? In this case, this word is like 付ける, which means "to attach." It's used for things you "attach" to your body to wear, like accessories, or a face mask. That's why this is to put on or to wear. Same sound, different kanji, similar ideas.
The reading is the same as 着く's reading, but it might be easier to think it shares a reading with 付ける, which has a similar meaning. Put on clothes, attach on clothes, etc!