70 entries under careful topic. ×

11
discriminating(adjective, characteristic, smooth, reasonable, sharp)
11
politic(adjective, cunning, wise, prudent)
11
sage(adjective, sound, reasonable, sharp, smart)
8
cautious(adjective, wise, clever, subtle)
7
wary(adjective, cunning, wise, prudent)
6
alert(adjective, understanding, sharp, bright)
6
discreet(adjective, reasonable, smart, sensible, skill)
6
far-sighted(adjective, smooth, reasonable, sensible, rational)
6
provident(adjective, sensible, wise, prudent)
6
rational(adjective, hard, sound, tough, reasonable)
5
sapient(adjective, sound, smooth, sharp, smart)
4
foresighted(adjective, sound, sharp, sensible)
4
reasonable(adjective, hard, sound, sensible, rational)
4
sane(adjective, hard, sound, reasonable, sensible)
4
vigilant(adjective, sensible, wise, tight)
3
leery(sensible, thoughtful, cunning, wise)
3
sound(adjective, hard, reasonable, sharp, smart)
3
thoughtful(adjective, sound, sharp, sensible, deep)
2
watchful(adjective, prudent, clever, subtle)
2
circumspect(adjective, wise, prudent, clever)
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APASmart Define. (2016). shrewd thesaurus. Retrieved September 29, 2026, from https://smartdefine.org/shrewd/thesaurus/synonyms
ChicagoSmart Define. 2016. "shrewd thesaurus" https://smartdefine.org/shrewd/thesaurus/synonyms (accessed September 29, 2026).
HarvardSmart Define 2016, shrewd thesaurus, Smart Define, viewed 29 September, 2026, <https://smartdefine.org/shrewd/thesaurus/synonyms>.
MLASmart Define. "shrewd thesaurus" 24 March 2016. Web. 29 September 2026. <https://smartdefine.org/shrewd/thesaurus/synonyms>