People have different interpretations of what it means to sag your pants. For The Wedgie Gang...ITS A DARE!
This is why The Wedgie Gang always have their underwear on full display. They’re daring people to attempt to wedgie them. Wedgie Gang members are experts at giving wedgies so it only makes sense that they be experts at avoiding them as well; therefore gang members are expected to ALWAYS have their pants sagging and underwear easily accessible no matter what; to pull their pants up is in their eyes a sign of weakness.
Of course this philosophy also goes beyond the gang itself. They see any intentional saggers as individuals who are confident they can avoid their wedgies and therefore challenging them to give it their best shot.
Meet Clyde and Blabbit. The Wedgie Gangs rivals!!!
DUN DUN DUUUUUUUUN!!!! XD