What do you think they should wear?

What do you think they should wear?

1. Jen's party is tonight and I want to look trendy. You should wear ____________________.
2. I have a meeting with Mr Richards in his office. You should wear ____________________.
3. It's snowing and I want to go out. You should wear ____________________.
4. I want to go jogging. You should wear ____________________.
5. Oh no, it's raining! You should wear ____________________.