depends on the dress code. for a more formal approach wear a two piece suit, for more of a casual setting i would recommend wearing a blazer, dress shirt, jeans and dress shoes. good luck!
definitely navy. never been a fan of gray.
good question! personally, i think it looks a little dated. id prefer wearing a cardigan instead (something with a shawl for extra style points). however, it depends on what type of look you’re going for. if your tastes cater to more of a british aesthetic i would say go for it. good luck!
no break! it looks baggy to me! its all about the cuff!