A condescending smile from someone who has a need to elevate themselves as better than someone else who may be suffering. A pity smile is actually self centered, and not truly compassionate nor empathetic.
The woman who walked by the homeless man looked down on him gave the man a pity smile.
Pajama casual is a term used when working from home and preparing for a video conference. All business above the waist and your pajama pants down below.