Meant to add this to my earlier post - I like this a lot. I wish I had the sack to try shit like this out, but alas, I do not.
Truth be told, even I can recognise the differences between the ensemble you like and the one you did not - the underlying factor being that one was thrown together and the other was more considered. The fact that the older one was professionally captured does help, also
I really miss those grey striped slacks