In my opinion -- the previous outfits were obviously worn that way intentionally, to be hip or whatever. The new one looks like trying but not quite getting there. If I were in your square-toed shoes I'd keep up what I know, working on the other stuff privately at home and posting pics until I'm sure I had it down. Only then would I go out in public in it.
Dude, have you seen what most people wear in public, IMO i wouldnt worry about.