Green’s Dictionary of Slang

chilly adj.

[SE chilly, cold/chill (out) v.]

1. emotionless, withdrawn, detached.

[US]Ade Artie (1963) 30: I goes in—purty chilly too.
[US]S. Lewis Our Mr Wrenn (1936) 198: It was great to be in England – though the people there are kind of chilly some ways.
[US]H.C. Witwer Classics in Sl. 63: ‘Mr. Windsor-Blenheim,’ she says, plenty chilly, ‘is this meant to be rude?’.
[US]C. Cooper Jr Scene (1996) 34: The boosting girls became chilly and demanding in their attitudes.
[US]H. Rhodes Chosen Few (1966) 163: Aw man, that’s kinda chilly, ain’t it? All of a sudden you don’t even know th’ chick’s name.

2. (orig. US black/campus) acceptable, satisfactory, calm.

[US]Eble Campus Sl. Apr. 2: chilly – calm.
[US]Eble Campus Sl. Oct. 3: chilly – in order; O.K.
[US]Eble Campus Sl. Spring 2: chilly – fine, in harmony or balance: Don’t worry. Everything is chilly.
[US](con. 1970s) G. Pelecanos King Suckerman (1998) 176: ‘Everything’s chilly,’ said Russell.
[US]G. Pelecanos Right As Rain 20: You need to give our client back her money, Leon [...] Then everything’ll be chilly.

3. (US black) attractive, fine.

[US]Break Machine ‘Break Dance Party’ 🎵 I’m gonna press my chilly duds.
[US] W. Safire What’s The Good Word? 79: Some words that are used in black slang here are: [...] looking chilly (looks nice) and crib — means ‘home.’.

4. cold-blooded.

[UK]Guardian G2 30 June 12: The tales he told got chillier and chillier.

5. skilful, competent at a given task or profession.

[US]F.X. Toole Rope Burns 175: You so chilly, why don’t you go on back and whup the boy?

In compounds

chilly down (v.) [chill (out) v. (3)]

(US) to pass the time of day, to ‘hang out’.

B. Cosby Fatherhood 116: He can say ‘chilly down’ so much that he sounds like a short order cook [HDAS].
chilly most (n.) [most, the n.]

(US black) a relaxed, composed person, an excellent admired person.

[US]Run DMC ‘Krush Groovin’’ 🎵 I rock parties from coast to coast / I’m know to the world as chilly most.
[US]Beastie Boys ‘The New Style’ 🎵 Taxing all females from coast to coast / And when I get my fill I’m chilly most.
[US]Bentley & Corbett Prison Sl. 48: Chilly Most [...] A calm, relaxed composure with a tranquil state of mind.
[US]Quicks Lettering/Decals ‘Word Ideas’ 🌐 chilly most Someone who is very cold; a paragon of chill.

In phrases

lay chilly (v.)

(US) to lie low.

[US]J. Webb Fields of Fire (1980) 71: They’re laying chilly out there. Wouldn’t come back with me.
play it chilly (v.) (also act chilly, hang chilly)

to act in a cool, controlled manner.

[US]H. Simmons Corner Boy 44: You got to play it chilly.
[US](con. 1950s) D. Goines Whoreson 143: This was an ideal time to act chilly but my defence was weakening.
[US]S. Morgan Homeboy 228: OK, Speaker. Play it chilly.
[UK]J. Mowry Six Out Seven (1994) 151: Hang chilly, Tam. Sabby been through a lotta changes today.

SE in slang uses

In compounds

chilly dog (n.)

(US campus) beer.

[US]Eble Campus Sl. Apr. 3: chilly dog – beer: We ordered a few chilly dogs with our pizza.
[US]Eble Sl. and Sociability 70: Dog is often the second member of a compound or phrase: [...] brew dog, chilly dog ‘beer’.
Cultgoespop 🌐 I’ll be a camp counselor and you can be an underage yet sexy camper looking for the marshmallows that you left behind at the bonfire we can start to get it on and end nicely with a chilly dog.