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1.
A nickname and/or hash tag given to someone that stays high, jumps high, or is better than everyone else in general.

1) Highfliy is "I Fly High" written as one word.

2)"I Fly High" refers to being above all the rest of the competion
Highfliy Gates is probably the most baller rich nerd ever, especially since Steve jobs died
by @treyhighfliy November 27, 2011