i think you should taper those attachments. i want to do the same but i don't know where to go to do it because of its shape. don't want to end up with some botched hybrid between j shaped and straight jeans.
I don't usually do this, but to me the polo fits great on the arm (mid bicep) but maybe see if you can find some polos with 4-5 buttons and smaller/thiner collars so they won't spread out like that and give you more room around the neck, that being said a nice shirt you can roll up is vastly better. Also I would taper the jeans/pants .5 to an inch just from the knees down. If you aren't comfortable going sans socks I would buy some thinner ones or no-shows (I buy cheap ones on ebay). Shoes look fine to me. This is all of course just my opinion