The loser buys a transparent backpack, every league member contributes one embarrassing (legal, work-safe) item, and the loser carries it everywhere for a league-set period with contents on full display. The curation meeting is the league's favorite night of the year. Removing or rearranging items is a violation.
The long haul: this is not a one-afternoon sentence. With a time commitment of one week to one month, the punishment keeps paying out (for everyone else) long after the season ends. Long sentences need a written end date and a league-appointed enforcer who checks compliance.