What it means
A kind little lift you give someone when life's gone a bit grim and you don't want them sinking into the carpet. It means stay brave, keep your head up, don't let one rough patch flatten your whole spirit. Said warmly, it's proper comforting. Said too fast, it can land a bit postcard-cheery.
Usage examples
"Keep your chin up, yeah? You’ve been dumped and your bus pass has vanished, but we’ll grab a chippy tea, have a moan, then crack on."
"Keep your chin up, the results aren't out yet and you reckoned the exam went alright."
"I know it's a rough week, but keep your chin up, payday's Friday and we'll sort it."
"Keep your chin up, mate. Today’s been a bin fire, I know, but tomorrow might stop acting feral."
"Keep your chin up, love. One bad call doesn’t mean the whole week’s cursed."
Where it comes from
It grows out of older English body language where holding your chin up signalled courage, pride, and not being cowed. By the late 1800s, chin up was already used to tell people to stay cheerful or brave under pressure. Keep your chin up became the fuller everyday version and stuck hard.