The winged death’s head was a grim reminder that life was short, not that one need’s that reminder as they stroll through a cemetery.
Slowly the imagery began to change. Though it is not as stark as the skull, it is still spooky. This haunting visage was somewhere between the skull and the chubby winged cherub’s that came next.
The image of a cherub’s face with curled wings circling upward became a popular symbol in the 18th Century. The winged cherubs replaced the stark and morbid flying death’s heads from our Puritan forefathers. The cherubs have a childlike countenance of innocence. The iconography represents the flight of the soul from the body upward to Heaven and the hope of the resurrection.
Gravely Speaking 
The earliest gravestones were populated by grim reminders of the inevitability of death: skulls and crossbones, winged hourglasses. These reflected a heavy Puritan influence: life was nasty, brutish and short and only a select few would make it to heaven. Everyone else was a sinner in the hands of an angry God. Often, stones with this type of motif mention something blunt like “Here lies the body”—there was no softening of the blow of death. Puritans were wary of succumbing to idolatry so the grim reminder of death was the only acceptable form of grave decoration.