The word is from Old English "prættig" which means "cunning"
By the 15th century, people used it to describe something that is made cleverly or artful.
Over time, the modern use for the word pretty is not used to describe someone who is attractive and good-looking or pleasing to the eyes. The word is often thrown as a compliment, mostly towards females.
There are, however, ironic ways to use "pretty". Phrases like "pretty pass" or "pretty state of affairs"
The word is an Old English word that meant swift or active.
By the 15th century, the word had emerged many different meanings ranging from being handsome to someone who is skillful. Expressions such as "tall of hand" and "tall of tongue" also arose which meant that this person was handy and good at arguing, respectively.
In the 16th century, the word tall has been used for subsequent metaphorical extensions like how large meant "tall order".
This word came from Old English where it meant happy or fortunate. As time passed it then got associated with "piousness" and "holiness" because the innocent are easily taken advantage of and the word "silly" came to signal a person who they deemed weak or helpless.
In addition to that, the negative associations to the word "silly" increased to the point where it started to mean that the person lacked sophistication thus the emergence of the modern sense of "foolishness".