I might do a v-neck with a button up, I won't wear a tie unless it is a more formal occasion or I get a better job, the place I work now is business casual so I don't want to go too formal. I have my eye on some AEs on ebay right now, so don't worry the better shoes are coming. In the meantime I have some other oxfords that I can wear that don't have the raised toes. Regardless of what others may think, I like the hat, I am going to trade the one in that picture for a smaller size, it is a tad too big.
It is good you like the hat. I don´t. Men over 65 might pull it of but not you and not with that outfit.