Derived in reference to the 1651 Sumptuary Law in the Massachusetts Bay Colony, enacted by the Puritans, barring anyone with less than 200£ from wearing "great boots," this design mimics the Puritan gravestone art of Wakefield MA.  The wearer, a lover of New England history, "Depart'd Mass 2018 Aged 41" (for work in the Midwest), and the winged heads wishfully call him to Rise Again home to the Commonwealth.  The pull-hole patterns reflect Nor'easter storm visuals.