This style of Maple Leafs jersey had it's origins in the NHL 75th anniversary season of 1991-92 when each of the Original 6 teams wore a throwback jersey, the Maple Leafs being based on their 1938-1958 style sweaters. The jersey was so well received that the basic jersey style became the basis for Toronto's new 1992-93 jerseys, only now with the retro maple leaf crest made into a secondary shoulder patch while the team's current modern maple leaf crest remained for used on the front.
This new jersey style was used unchanged until 1997-98 when an unfortunately modern name and number font was employed through 1999-00. Toronto then went back to a more traditional number font, while retaining the new font for the names on the back. Other new additions were the new "TML" monogram for the secondary shoulder patches as well as silver trim around the numbers and monogram. This third generation of today's featured style was employed through the 2006-07 season when the entire league got new jerseys in the change to the new Reebok Edge jerseys.
The story goes that the original plan was for the new Edge jerseys to be tucked into the player's pants, so the Maple Leafs jerseys were created without any waist striping and lacked any shoulder patches, leaving an extraordinarily plain looking jersey. Still, it would last until 2009-10 until the Maple Leafs would return to a nearly identical Edge version of today's featured jersey (including the return of the retro leaf shoulder patches) for the 2010-11 season, only now with the addition of a retro lace-up collar as used from 1958 to 1967.