A characteristic, mannerism, or appearance of a person, either subtle or overt, which implies unique, eccentric, creative, adventurous or unconventional thinking.
David Crosby refers to long hair as a freak flag in his song Almost Cut My Hair. "I feel like letting my freak flag fly."

Movie Character Ben compliments Meredith in The Family Stone, "You have a freak flag...you just don't fly it."
by Anthony T. White May 22, 2006
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Letting loose, being down with your cool self, especially in front of a group of strangers. Your inner freak, that wants to come out, but often is supressed, from social anxiety.
Ang: "Hey T-Rev, whatcha doin this weekend bra?"

Trev: "Ang, I'm gonna fly my freak flag!"
by Freaky Ang May 8, 2006
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Unrestrained, unorthodox or unconventional in thinking, behavior, manners, etc. One who espouses radical, nonconformist or dissenting views and opinions that are outside the mainstream.
When traveling through the bible belt of the US, it's best not to let your freak flag fly high. Otherwise, you'll be harassed and attacked by these backwater, backward thinking theocrats.
by Preston Pierce March 12, 2011
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1.) David Crosby's penis
2.)Jimi Hendrix's penis
David Crosby: "I feel like letting my freak flag fly"
translated to "I'm going to have sex with mad bitches because it's the 60's and I can"

Jimi Hendrix: "But I'm going to wave my freak flag high...HIGH"
translated to "I have a massive erection"
by freakflag April 3, 2010
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A flag, of sorts, strung up a pole at an outdoor concert/festival to signify where your seats are.
Our freak flag was so cool, i could find my buds no matter what i was on.
by Charles L. May 3, 2006
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1. Your inner party animal. "Letting your freak flag fly" means acting wild. See crazy.
2. An unsigned shock-metal/industrial metal band from Canada.
1. I'm gonna let my freak flag fly!
2. Dude, Freak Flag is fuckin' awesome!
by That Stupid MF September 1, 2007
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The labia minora that protrude so much so, that they flap in the wind like the good ol' flag!
AKA: Bacon Gliders, Pastrami Box, Roast Beef Curtain.
At the nude beach, Shelly had no problem letting her freak flags flap in the breeze.
by Princess Freak Flag May 11, 2010
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