Start by putting a shoe tree in each boot so your boots don't lose their shape. Then, use a suede brush or an old toothbrush to gently brush the surface...
I think dry is the best option. It makes it a lot easier to identify cowlicks and anticipate the way the bangs are going to look when they're hanging naturally.
No, your skin has to be drenching wet. It's a super common misconception, but your skin has to be totally soaked. You cannot apply makeup to dry skin, period.