it's a comical way to say "keep going" or "push through" or whatever. its supposed to be an encouraging quote and usually serves its purpose, also making that person smile
"dude i've been so sad. i can't believe he left me for that other girl"
"hey, keep your head up princess, your tiara is falling"
A sly way of calling a girl as perfect and graceful as a princess when cheering her up. An encouragement to just keep standing proud.
Girl: Ugh, literally nothing is going right today. I fell flat on my face in the audition, and my best friend is not talking to me anymore. I just feel so awful.
You: Oh that's awful! You deserve way better than that. Just Keep Your Head Up Princess, Your Tiara Is Falling
Fogey/fogy /fougi/ sl. (early 18C+, orig. Scot) old-fashioned, stuck-in-the mud.
Person with old fashioned ideas which he is unwilling to change: Come to the disco and stop being such an old fogey!
You think me an old fogeyand an old tory, his thoughtful voice said. I saw three generations since O’Connel’s time. I remember the famine. Do you know that the orange lodges agitated for repeal of the union twenty years before O’Connel did or before the prelates of your communion denounced him as a demagogue? You fenians forget some things. (James Joyce, Ulysses. PenguinBooks,1992. p. 38)