It's a good question. What is meant by the term "grown up" in relation to clothes? I still see men in their 70s wearing jeans and T shirts and it suits them. Personally I wear less jeans and more trousers these days because I think they suit me better. If I could get away with wearing jeans I'd probably wear them more often. Image is everything.
Not sure if Loake export to the US unless it is a specialised retailer. Was looking at some desert boots in the shop window the other day. I'm not sure what brand they were but they were blue suede with white stiching. The sole and heel(half inch) were light tan leather. Real nice
it depends on the shade of charcoal.
Shirt colour: Light blue, white, pink/purple, maybe plain, striped or windowpane check.
Tie colour: Would only probably consider navy or purple with maybe a bit of shirt colour in there. I'd avoid plain ties or large paterns, except maybe stripe. Go for complimantary colours for the pocket square or different shades of the shirt/tie combo.
Not sure what you mean. Largely the lapel size of the jacket dictates the width of the tie. i.e. wide lapels of the 1970s require a kipper tie. You wouldn't wear a skinny tie when the lapels of your jacket are reaching out towards your armpits.
Difficult question but I like the kent knot although the half winsor is good. I guess it all depends on the shirt collar type, high/low, collar spread, collar shape, pin, tab etc. I also consider the effect with the jacket lapels when tieing a knot.