Let your freak flag fly

First Example:

Nancy: What are you wearing for the costume party?

Marco: I’m going to wear a bear hat, a penguin coat, and cheetah pants.  I’ll be the weird one of the party.

Nancy: You’re really going to let your freak flag fly, huh?

Marco: Thanks.  You know me; I’m always trying to be fun.

Meaning: "Let your freak flag fly" is a positive expression used to show a characteristic that’s hidden or overt implying a unique or unconventional way of thinking.  Some people feel that the work “freak” might be a bad thing, but in this instance, it’s a show of approval.

Second Example:

Barbara:  What do you think about my idea for the holiday party we all wear our clothes inside out?

Tom:  I’m not sure.  That seems a little crazy.  Don’t you think?

Barbara:  Oh, come on!  Let your freak flag fly!  Not everything has to be formal in life.

Tom:  You know what?  You’re right.  We should have a little fun in the office every now and again.

Meaning: In this instance, “Let your freak flag fly” is used to show a unique way of thinking, that although may seem strange, can be a positive thing.  Here Barbara is just trying to create a fun atmosphere for the day.  It doesn’t necessarily mean it’s a permanent condition or thought.

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