Definition of tippiest:
(adj) :
(Canada, US) Tending to tip or tilt over; unstable.
(adj) :
(colloquial or slang) Clever, neat, smart.
(adj) :
Of tea, having a large amount of tips, or leaf buds.
(adj) :
(obsolete, colloquial or slang) Fashionable, tip-top.
(n) :
(obsolete, colloquial or slang) A dandy.
(n) :
(obsolete, colloquial or slang, absolute, with the) Something at the height of fashion, excellent, cool.