Very well, I invite you all to check the spoiler, if you'd rather not guess.
Despair, and upgraded Despair.
As for what they actually depict...
Staring up at rainclouds, which conceal something unnatural within, causing a visible displacement.
The upgraded version has indistinct tendrils covering up the view, threatening to overcome it; that or they're the shadows of spires looming over the viewer.
It's open to interpretation.
Another attempt.
(https://i.imgur.com/NxoXPw1.png)
A closer look.
(https://i.imgur.com/gPcbt8W.jpg)
I'd been trying to think of what would make a person say "Ah yes, that's definitely Despair, it's the only possibility." for ages, when suddenly, tragedy struck.
That is to say, the word, not an actual event.
I liked the grittiness of the Skull Shield, so I tried to add some here as well.