pretty
/prĭt′ē/
adjective
  1. Pleasing or attractive in a graceful or delicate way. synonym: beautiful.
  2. Clever; adroit.
    a pretty maneuver.
  3. Very bad; terrible.
    in a pretty predicament; a situation that has reached a pretty pass.
from The American Heritage® Dictionary of the English Language, 5th Edition. More at Wordnik
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Merriam-Webster
merriam-webster.com › dictionary › pretty
PRETTY Definition & Meaning - Merriam-Webster
The meaning of PRETTY is artful, clever. How to use pretty in a sentence. Using Pretty as an Adverb: Usage Guide Synonym Discussion of Pretty.
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Cambridge Dictionary
dictionary.cambridge.org › us › grammar › british-grammar › pretty
Pretty - English Grammar Today - Cambridge Dictionary
We can use pretty as an adverb, before an adjective or another adverb, meaning ‘quite, but not extremely’. It is informal:
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Dictionary.com
dictionary.com › browse › pretty
PRETTY Definition & Meaning | Dictionary.com
The qualifying adverb pretty, meaning “fairly or moderately” has been in general use since the late 16th century. Although most common in informal speech and writing, it is far from restricted to them, and often is less stilted than alternatives such as relatively, moderately, and quite.
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Quora
quora.com › Is-pretty-a-verb-or-an-adjective
Is 'pretty' a verb or an adjective? - Quora
On the contrary, the word “pretty” functions not only as an adjective, but also as an adverb (adverb of degree). As it is, whereas “pretty,” as an adjective, modifies a noun, “pretty,” as an adverb, modifies an adjective.
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Vocabulary.com
vocabulary.com › dictionary › pretty
Pretty - Definition, Meaning & Synonyms | Vocabulary.com
If you say, “That’s a pretty mess you got me into!” that means it’s a bad mess. Pretty has an adverb form that means something is present to a moderate degree, another way to say fairly.
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WordType
wordtype.org › of › pretty
What type of word is 'pretty'? Pretty can be an adverb, a noun, a verb or an adjective - Word Type
... pretty can be used as a adjective in the sense of "Cunning; clever, skilful." or "Pleasant in sight or other senses; attractive, especially of women or children." or "Of objects or things: nice-looking, appealing." or "Fine-looking; only superficially attractive; initially appealing but ...
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Speak Confident English
speakconfidentenglish.com › home › #211: pretty much, pretty sure meaning — use pretty as an adverb
Pretty Much, Pretty Sure Meaning — Use Pretty as an Adverb
July 14, 2021 - Native speakers use pretty to soften an adverb or adjective. We use it to replace words like “fairly”, “slightly”, and “quite”. I’m pretty certain that Tony will be here on time.
Find elsewhere
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Oxford Learner's Dictionaries
oxfordlearnersdictionaries.com › definition › english › pretty_2
pretty adjective - Definition, pictures, pronunciation and usage notes | Oxford Advanced Learner's Dictionary at OxfordLearnersDictionaries.com
(figurative) He was hired to make the company pretty and then sell it off. Oxford Collocations Dictionaryverbs · be · feel · look · …adverb · extremely · fairly · very · …See full entry · Word OriginOld English prættig; related to Middle Dutch pertich ‘brisk, clever’, obsolete Dutch prettig ‘humorous, sporty’, from a West Germanic base meaning ‘trick’. The sense development ‘deceitful, cunning, clever, skilful, admirable, pleasing, nice’ has parallels in adjectives such as canny, fine, nice, etc.
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Collins Dictionary
collinsdictionary.com › dictionary › english › pretty
PRETTY definition and meaning | Collins English Dictionary
... to pretty up a room SYNONYMS 1. See beautiful. 2–4. pleasant. 10. somewhat.ANTONYMS 1. ugly.USAGE The qualifying adverb pretty, meaning “fairly or moderately” has been in general use since the late 16th century.
Published   March 20, 2018
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Encyclopedia Britannica
britannica.com › dictionary › pretty
Pretty Definition & Meaning | Britannica Dictionary
◊ Someone who is not just a/another pretty face or more than (just) a pretty face is attractive but also has other good qualities, such as intelligence. If he wants to get people to vote for him, he's got to prove he's more than just a pretty face. [+] more examples [-] hide examples [+] Example sentences [-] Hide examples · /ˈprɪtəli/ adverb ·
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Oxford English Dictionary
oed.com › dictionary › pretty_adv
pretty, adv. meanings, etymology and more | Oxford English Dictionary
OED's earliest evidence for pretty is from 1565, in the writing of Thomas Cooper, theologian and bishop of Winchester. It is also recorded as an adjective from the Old English period (pre-1150). ... To continue reading, please sign in below or ...
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Oxford Learner's Dictionaries
oxfordlearnersdictionaries.com › us › definition › english › pretty_1
pretty adverb - Definition, pictures, pronunciation and usage notes | Oxford Advanced Learner's Dictionary at OxfordLearnersDictionaries.com
With some adjectives, both meanings are possible. The speaker’s stress and intonation will show you which is meant: Your essay is quite good (= fairly good—it could be better); Your essay is quite good (= very good, especially when this is unexpected). In North American English quite usually means something like ‘very’, not ‘fairly’ or ‘rather’. Pretty is used instead for this sense.
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Promova
promova.com › what-part-of-speech › pretty
What part of speech is the word pretty? — Promova
as an adjective, 'pretty' describes something or someone as attractive in a delicate or endearing way. ... She wore a pretty dress to the party. The garden looks pretty in the springtime. He gave her a pretty bouquet of flowers. ... It's essential to differentiate between the adjectival and ...
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Primavera English
primaveraenglish.com › word-of-the-month-pretty
Word of the Month: pretty | Primavera English
Pretty is a pretty common word in English, because it has an adjective, adverb, and verb form. You will most often hear it being used in its adverb form, where it means “moderately,” or “quite.” Note that it is different from very or ...
Top answer
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As FumbleFingers says, this is a pretty old use, going back to Early Modern English:

Pretty (pri•ti) adv. Forms: see prec. [The adj. in adverbial use.]
 1. To a considerable extent, considerably; in a fair or moderate degree, fairly, moderately, tolerably; [...]
1598 FLORIO Dict. Ep. Ded. 3 Boccace is prettie hard, yet understood: Petrarche harder but explained. —OED 1

(I offer this OED 1 citation rather than the earlier one reproduced by FumbleFingers because I am not convinced that the use in the earlier citation is adverbial.)

Pretty has a complicated history, as you may see from the OED 1 entry which immediately precedes the link above: from cunning, artful to clever, skilful to ‘a general epithet of admiration or appreciation... fine, pleasing, proper’, and so forth, leading to the main modern sense ‘having beauty without majesty or stateliness’; but the origin of this adverbial use clearly lies in OED 1 sense 5 for the adjective:

 5. Considerable in number, quantity, or extent, as in a pretty deal, while, way, etc.; also a pretty many = a good many; ...

OED 1 gives citations for this use dating from c. 1485 down to 1861, but marks it as ‘Now arch. or dial.

I am surprised you did not find this in any dictionary; I found it in the first three online dictionaries I checked, Collins, Oxford, and Merriam-Webster. All three post definitions for the adverb after those for the adjective.

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Perhaps it has to do with French influence after the Norman conquest from the expression "près de" (near) since it means "close to" or "right up to"? I have NO evidence of this. Does anyone? This just came to mind.

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Wiktionary
simple.wiktionary.org › wiki › pretty
pretty - Simple English Wiktionary
You use pretty before an adjective or adverb to mean "more than a little".
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Reddit
reddit.com › r/words › how did "pretty" come to mean "sort of" or "somewhat?"
r/words on Reddit: How did "pretty" come to mean "sort of" or "somewhat?"
October 28, 2024 -

How was your day?

Pretty good.

How or why did this happen to this word which originally meant beautiful, pleasing to the eye, etc?

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Merriam-Webster
merriam-webster.com › thesaurus › pretty
PRETTY Synonyms: 444 Similar and Opposite Words | Merriam-Webster Thesaurus
Read More Opinions expressed in the examples do not represent those of Merriam-Webster or its editors. Send us feedback. ... Adjective Behind the pastry case out front, where pistachio pain suisse and chocolate-chunk cookies sit pretty, is a quiet, serious kitchen. —Sarah Blaskovich, Dallas Morning News, 9 Mar. 2026 The line now includes fragrances such as Grace and Wake, in travel size sprays and pretty glass bottles, and in moisturizing hand creams. —Karen Billing, San Diego Union-Tribune, 9 Mar. 2026 · Adverb That's come pretty naturally to me.
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Cambridge Dictionary
dictionary.cambridge.org › us › dictionary › english › pretty
PRETTY | definition in the Cambridge English Dictionary
Nothing really changes around here. One day is pretty much like the next. ... PrettyWe can use pretty as an adverb, before an adjective or another adverb, meaning ‘quite, but not extremely’. It is informal: …