Synonyms of guileful

guileful

adjective

1

as in cunning

clever at attaining one's ends by indirect and often deceptive means

tried to fix the game with a guileful plot to sabotage the other team's bats, but the umpire caught them

Synonyms & Similar Words

• cunning
• cute
• slick
• subtle
• deceptive
• fraudulent
• dishonest
• wily
• treacherous
• shrewd
• devious
• sly
• artful
• crooked
• scheming
• beguiling
• crafty
• tricky
• foxy
• deceitful
• cagey
• designing
• dodgy
• shady
• slippery
• unscrupulous
• sharp
• calculating
• astute
• glib
• covert
• Machiavellian
• sneaky
• oblique
• shifty
• underhanded
• knavish
• insincere
• facile
• clandestine
• hypocritical
• serpentine
• plotting
• undercover
• underhand
• circular
• circuitous
• secret
• roundabout
• concealed
• smooth-tongued
• stealthy
• surreptitious
• backhanded
• furtive
• insinuating
• double-dealing
• two-faced
• mealy
• left-handed
• mealymouthed
• hugger-mugger

Antonyms & Near Antonyms

• ingenuous
• guileless
• artless
• innocent
• obvious
• public
• plain
• real
• simple
• straightforward
• sincere
• open
• forthright
• direct
• honest
• frank
• unconcealed
• natural
• outspoken
• unpretentious
• unaffected
• unsophisticated
• candid
• childlike
• impressionable
• unpretending
• patent
• unvarnished
• aboveboard
• simpleminded
• unworldly
• undesigning
• unstudied
• unforced
• plainspoken
• trustful
• trusting

2

as in deceptive

given to or marked by cheating and deception

received a guileful answer when I asked the dealer if the used car had ever been in a collision

Synonyms & Similar Words

• deceptive
• fraudulent
• shady
• crooked
• dishonest
• false
• duplicitous
• fast
• shifty
• underhanded
• rogue
• underhand
• artful
• sharp
• bent
• unscrupulous
• cunning
• double-dealing
• deceitful
• treacherous
• unprincipled
• wily
• subtle
• unethical
• delusive
• sly
• deceiving
• beguiling
• unconscionable
• devious
• crafty
• insidious
• slippery
• perfidious
• foxy
• sneaky
• slick
• cagey
• delusory
• tricky
• furtive
• deluding
• trickish
• defrauding
• sneaking

Antonyms & Near Antonyms

• honest
• straight
• ethical
• honorable
• conscientious
• scrupulous
• decent
• upright
• aboveboard
• just
• straightforward
• forthright

Example Sentences

Recent Examples of guileful

Bruno Guimaraes and Lucas Paqueta played guileful defence-splitting passes. — James Horncastle, New York Times, 20 June 2026

One is to emphasize Iago—the guileful, insinuating convincingness of this malicious supervillain, who works on Othello to the point where any reasonable man would be deceived and fooled and worked into a rage that can lead to such a catastrophe. — David Frum, The Atlantic, 17 June 2026