Definitions

streetwise

[street-wahyz] / ˈstritˌwaɪz /

ADJECTIVE

canny

Synonyms

STRONGEST

adroit astute cagey cautious discreet frugal ingenious intelligent judicious prudent shrewd skillful sly subtle wise

WEAK

able acute careful circumspect cunning dexterous foxy having fancy footwork hep knowing nimble-witted perspicacious quick quick-witted sagacious slick slippery smart smooth street smart wary watchful with it worldly-wise

Antonyms

STRONGEST

awkward careless foolish hasty honest idiotic ignorant imbecile imprudent incautious inept open rash reckless stupid thoughtless uncareful unintelligent unskilled unwise

WEAK

silly

ADJECTIVE

competitive

Synonyms

STRONGEST

aggressive ambitious competing cutthroat vying

WEAK

antagonistic at odds combative dog-eat-dog emulous killer killer instinct opposing rival

Antonyms

WEAK

noncompetitive unambitious

ADJECTIVE

crafty

Synonyms

STRONGEST

astute cagey canny devious insidious shrewd slick sly wily

STRONG

intelligent smart subtle

WEAK

adroit artful calculating crazy like fox cunning deceitful designing disingenuous duplicitous foxy fraudulent guileful keen knowing sharp slippery smooth street smart tricky vulpine

Antonyms

STRONGEST

honest open straightforward

WEAK

naive

ADJECTIVE

cunning

Synonyms

STRONG

Machiavellian acute deep keen knowing sharp slick smart smarts smooth

WEAK

artful astute cagey canny crafty crazy like fox fancy footwork foxy guileful insidious shifty shrewd slippery sly sly boots street-smart subtle tricky wary wily

Antonyms

STRONG

aboveboard blunt coarse dull ignorant obtuse rough slow stupid unintelligent unstylish

WEAK

gullible kind naive shy unclever unimaginative

ADJECTIVE

savvy

Synonyms

STRONG

acute calculating cunning discerning experienced keen knowing sharp slick smart smooth wise

WEAK

astute brainy cagey canny clever crafty farsighted foxy heady in the know ingenious intelligent judicious on the ball perceptive sagacious sensible sly

Antonyms

STRONG

blunt coarse dull ignorant inexperienced kind naive obtuse rough slow stupid unclever unintelligent unstylish

ADJECTIVE

shrewd

Synonyms

STRONGEST

astute cagey canny crafty farsighted ingenious judicious keen penetrating perceptive probing prudent sensible sharp slick sly smart wily wise

WEAK

acute argute artful astucious brainy calculating cunning cutting deep discerning discriminating foxy heady in the know inside knowing on the inside on top of perspicacious piercing profound quick-witted sagacious savvy shark slippery smooth tricky underhand up on wised up

Antonyms

STRONGEST

blunt dull foolish honest idiotic ignorant inept obtuse senseless slow stupid unclever unintelligent unreasonable unstylish unwise

WEAK

frivolous naive unthinking

ADJECTIVE

slick

Synonyms

STRONGEST

deft glib sharp shrewd skillful sly smooth sophisticated

STRONG

knowing polished professional quick wise

WEAK

adroit cagey canny dextrous foxy plausible smooth-spoken specious unctuous urbane

Antonyms

STRONGEST

ignorant naive simple slow stupid unskillful

WEAK

amateurish clumsy coarse rough unclever unintelligent unpolished

ADJECTIVE

sophisticated

Synonyms

STRONGEST

mature practical refined worldly

STRONG

bored citified cool cultivated disenchanted disillusioned experienced jaded knowing practiced schooled seasoned smooth studied

WEAK

adult artificial been around blasé couth cynical in in the know into jet-set laid-back mondaine on to sharp skeptical stagy suave svelte switched-on uptown urbane well-bred wise to wised-up with it world-weary worldly-wise

Antonyms

STRONGEST

inexperienced unrefined unsophisticated

STRONG

enchanted encouraged enthusiastic excited uncool

WEAK

easy naive simple slow uncultivated uncultured

ADJECTIVE

street-smart

Synonyms

STRONGEST

hardened

WEAK

astute cunning experienced on the ball quick-witted savvy seasoned shrewd worldly

Antonyms

WEAK

inexperienced naïve

ADJECTIVE

street smart

Synonyms

WEAK

artful astute cagey calculating canny clever crafty cunning experienced foxy ingenious intelligent perceptive quick-witted savvy seasoned sharp slick sly smart smooth wily wise

ADJECTIVE

tricky

Synonyms

STRONGEST

shifty slippery smooth subtle treacherous

WEAK

artful astute cagey catchy clever crafty cunning deceitful deep delusive delusory devious dishonest foxy greasy guileful insidious intelligent keen misleading scheming shady sharp shrewd slick wily witted wry

Antonyms

STRONGEST

forthright honest

WEAK

aboveboard frank

ADJECTIVE

wily

Synonyms

STRONGEST

cagey crooked scheming shifty shrewd sly sneaky underhanded

WEAK

arch artful astute crazy like a fox cunning deceitful deceptive deep designing foxy greasy guileful insidious intriguing knowing sagacious sharp slick slippery smooth tricky

Antonyms

STRONGEST

aboveboard forthright frank honest open straight

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

Read the rest of this week’s Streetwise column here.

From Barron's • Apr. 24, 2026

Blankfein, who is retired and in recent weeks has been promoting his memoir Streetwise: Getting to and through Goldman Sachs, said he missed being involved in what he termed crisis moments.

From MarketWatch • Mar. 26, 2026

Streetwise was cautiously skeptical both about the biggest claims of AI proponents and that this was a bubble.

From The Wall Street Journal • Dec. 28, 2025

Streetwise and informed by Price’s trademark dialogue and gallows humor, it’s a tale of individual redemption and an exploration of the precarity of American life.

From Los Angeles Times • Sep. 3, 2024

Streetwise was what he needed to be after his family moved to Wythenshawe, the huge social housing estate on the edge of Manchester.

From BBC • Dec. 6, 2023

streetwise

Example Sentences

Related Words