Milo Cash walked into the Shatterdome, he did some minor training of hand to hand before ever wanting to be a Jaeger pilot, being from Britain it didn't seem needed but things escalate daily and it never hurts to be prepared. The beanie being the one thing he never left even though he's lost about everything once, and now losing most of his life to the Kaijus. One of the other things he almost never left was his trusty headphones for when he needed the music, being a great focus especially during a fight. 

He was ready for a new war now, ready to finally kill the S.O.B's that ruined his life back home.