Well it's B.o.B., flyer than a stewardess

from B.o.B (Ft. Andre 3000) – Play the Guitar Lyrics on Rap Genius

Meaning

Something about a uniform that makes anyone look “fly”.
Consider stewardesses “double fly”, as they are dressed appropriately and are 30,000+ feet in the air while looking fly.

If B.o.B. is flyer than a stewardess… that’s pretty damn fly!

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