slyboots
Word family
Synonym discussion
Sense: noun/1
'Slyboots' is older and more playful than most near-synonyms. You use it for someone who hides what they are planning and enjoys surprising people with a clever, slightly dishonest move. 'Schemer' is more negative and suggests a longer plan for power, money, or control. 'Trickster' highlights clever jokes, cheating, or rule-bending, often with more energy than secrecy. 'Fox' can sound admiring as well as critical, because it praises cleverness. 'Sneak' is harsher and focuses on weak, unpleasant secrecy rather than wit. Compare: 'You slyboots, you hid the ring in the cake,' 'a schemer in the office,' 'a trickster at the card table,' and 'a sneak who reads other people's messages.'
Etymology
An old English nickname built around 'sly'. In this word, 'boots' is not used in its ordinary meaning of shoes; it survives as part of a humorous label for a crafty person. Modern speakers usually feel the first part clearly and treat the whole word as an old-fashioned, playful name for someone who keeps their real intentions hidden.
First known use
1700
1700, in the meaning defined above