Half-way house, I can't really tell from the picture. I have some chisels around one Inch and some around two inch. Maybe square starts at three inch I don't know. Still, what does it matter just so long as you like them?
Trousers are too long IMO, I don't like any roll around the bottom when stood up. If you're going to wear short sleeves to show off your cuffs make sure the length of the jacket is short too, yours looks a little too long. Hvae it shortened by 2 inches.
I'd say, wear what you want. Personally, I don't do fashion, I do clothes. I don't want to be like the majority of other people - why fit in when you can stand out?
The only thing I would say is that there are around three choices when putting together an outfit:
Colour: Should Compliment
Cut of garment in relation to what other piece of clothing you are wearing. Try not to mix styles and periods of clothing.
Texture. Try to avoid mixing course...
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.