Shadowlands

You search inside your room. You have a pair of rain boots. They are waterproof but uncomfortable to walk in for extended periods. You also have sturdy boots meant for snow, but they are extremely warm. You also have hiking boots. They are waterproof but haven't been broken in yet. They would be comfortable once broken in, but haven't been broken in yet.

You've stored your winter coats for the season. You have a sweatshirt and a rain jacket.

What is most important to pack?