Yes, Hook's boots annoy me too! They come to a big, clunky tip on the end, and curl up, I would presume just to make walking easier. Same reason I can't wear heels with pointed toes, because my feet are already big, and they just make my feet look even bigger, plus they squish my toes. Maybe next season he'll get some new boots.
At the beginning of 3B, there was a lot of talk about why Emma was wearing plaid all the time, and I just noticed that when 12 year old Emma is at the orphanage, she is wearing a plaid shirt. I'm not sure if she was unconsciously connecting to her past feelings of not having a home, or if she just likes plaid, but it was nice continuity.