Asking me how you so fly, yet you still so grounded?
They ask how come he has so much style, and ask how can he be humble with all that style?
“Grounded” and “fly” is a wordplay. They can mean “humble” and “stylish” respectively, but it’s also an allusion to an airplane, which can be grounded or flying. An airplane can have connotations of being high or of international travel, jet set, etc.
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