You know when you were a kid and your parent pressed the tip of your shoe to make sure they couldn't feel your toes so that your shoe had room to grow?
Yeah
The tips of his shoe look so empty because there's a hidden heel inside of the boot to give him some extra height so Trump doesn't make fun of him for being short.
I didn't grow up vegan so yeah, we just shoved our feet into whatever living animals they had at the store
He's wearing the shoes Kelley draws on his comic characters.
They're boots, dog. The guy is bringing out all of the cultural signifiers
Dark brown or black shoes are really the only acceptable shoes to wear with a blue suit; any other colors look garish and should not even be considered.
Client facing staff are expected to wear Rootin Tootin Formal attire.
The wide range of expressions on everyone's faces are something else
Dang, quick search didn't turn up any 10 inch men's dress boots (chelsea,maybe?, the cut of leather and heel shape seem right) with 3-4 inch lifts.