Oregon Trail Swag

Definition

The audacious confidence of someone who pioneers trends rather than following them; taking the unconventional road with enough swagger that it somehow becomes cool in retrospect.

Example Usage

He brought back crew cuts three years before they were trendy—that's pure Oregon Trail Swag.

Source: Urban Dictionary (https://www.urbandictionary.com/define.php?term=Oregon%20Trail%20Swag&defid=5584641)

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