Welcome and thanks for sharing. I think it's a cool look you have put together...
That shirt will most likely never serve you well when used with a suit and tie.
Agreed. The shirt just looks shabby, you need at least a crisp white shirt.
Citan, I also like your coat -- can you comment more on the fit? Is your build more athletic?
In regard to your need for new shoes -- Meermin might be a good option. I really like the double monks I just took shipment of.