During that time, the league has seen more than a few iconic jersey designs cross its path. Even teams that joined the league later, like the Edmonton Oilers, Pittsburgh Penguins, or San Jose Sharks, have been lauded for their jersey designs. There may be just as many, if not more, NHL designs that simply missed the mark entirely. The history of NHL jersey miscues is vast, but we were able to condense it into a list of the 14 worst to ever make it onto the ice, ranked from tolerable to downright ugly…14. Montreal Canadiens barber pole (2009-2010)No NHL jersey has induced more headaches to look at than this Montreal Canadiens centennial jersey.