Not sure if this is how you intend the dialogue to continue, but I will give my response to the above pics.
I don't like the look in either, but can 'respect' or appreciate the second pic (did not see the video in detail).
The first pic looks like he is trying to achieve a sober/ understated (harmonious?) look, bit something in the tie and the shirt, flower and square seems to work against the effect of the suit. If I think about it, the pattern - polka dot to stripes - seems jarring, the colors - red /blue/ white seem jarring, and that pocket square seems to have to add to the confusion.
The second pic I can appreciate because even though he's still wearing a 3 piece suit and striped shirt, now he's gone all the way into a more exuberant style. The tie, the hat, the coat - they all suggest the same thing, seem to be going to the same destination (although you may not want to go there yourself).