I believe, personally, that when it comes to "off script" it's about proportions. Or portions.

I am a man with some extra portions on my middle. I like to eat, what can I say? So a small shoe, or small boot look toooo small for me. I look like a snowman balancing on silts. Added to that the high socks, with a narrower ankle cause a "toothpick" effect, further exaggerating my rotund mid section. Visually I believe I need to balance my shoulder width with a larger shoe/boot. This gives a more solid grounding to the visual appearance.
So a heaver boot, through a narrower leg (I skip 'leg day' everyday), a wider lower mid, but a vested/cinched upper mid to create a slightly broader shoulder and to cover the waisband/shirt tuck area that speaks volumes about my volume.

If it's saturday morning and I'm making tea, it's my tea kilt and the black rock-band t-shirt of the day, untucked, because no one except my wife will see me, she hates tucked t-shirts, and I'm in it for comfort.