Is it the double buttoning of the collar that makes the collor look so stiff and high? its a distinguished look
Yes. most high collar shirts have 2 buttons...I guess you can still have a high collar made with just 1 button though.
His sleeve needs a 4th button.
the 4th is unbuttoned on purpose.
I'd lose the pant cuffs too, they are quite wide.
Extra wide cuffs are a very popular Italian look, and are very good for showing off your shoes. I think he should add a touch more length though.
I'd never even though about going out without cufflinks. I like it.
Doesn`t have to be a shirt for cufflinks though...You can do the same look with a button shirt.