‘Pretty’ is quite a versatile word because we use it in a variety of ways:

One can drive a pretty nice car.
A child, a pet, a garden, and a picture can all be pretty.
Pleasant or attractive music , noises or words sound pretty.
An ornament or decoration can be called a pretty.
Something expensive is said to cost a pretty penny.
Someone in a safe or comfortable position is sitting pretty.
A person can pretty themselves up for a special occasion.
A request or plea is made more emphatic and emotive when someone adds pretty please.

On a more negative note, someone who is in trouble or said to be in a pretty mess.
If someone or something is only moderately attractive, they might be described as prettyish.
An event or a relationship can be pretty much over.

It is also interesting in that none of those meanings relate to the original meaning of pretty.

Pretty comes from the Middle English word ‘pratie’ which meant cunning, crafty, or clever”
This is related to a number of Old English words:

• prættig – West Saxon
• pretti – Kentish
• prettig  – Mercian

These are all adjectives that mean cunning, skilful, artful, wily, or astute.

Before that, the words prætt or prett meant a type of trick, wile or craft. These words have a Proto-Germanic origin in *pratt- , which has closely related words in Old Norse , Frisian, Old Dutch, and Flemish.
Bt the beginning of the 15th century, pretty had evolved to also mean something manly or masculine, gallant, and something cleverly made.  By the mid 1400s, it had developed further to include the senses of attractiveness to the senses or holding aesthetic appeal, and of being slightly beautiful.

The use for pretty to express degree or amount developed by the mid 1500s, and pretty much had evolved by the mid 1600s.

A collection of pretty tho gs was called a prettiness in the late 1600s, while the use of pretty as a noun, such as “my pretty” developed in the 1700s, first in reference to things and then people.

The earlier meaning related to masculinity,  bravery and cleverness did an about-turn by the late 1800s, when the term pretty-boy came to be used as a derogatory term for any man deemed to be effeminate or suspected of being a homosexual.

In the early 1900s, pretty became a verb, meaning to make something or oneself more attractive.

It turns out that pretty is more than just a rather versatile word: it’s also fairly old and quite interesting.

Sources:
Macquarie Dictionary
Etymonline

Pretty.
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