But here's the weird thing: Rich Uncle Pennybags never had a monocle. Seriously, go to your closet and dig up the Monopoly box inevitably buried near the back. And before you ask, no, his design hasn't changed at all since he was introduced in Monopoly's Community and Chance cards in 1936:
He's as constant as the concept of economic malfeasance.
The most likely explanation for this widespread confusion is the existence of another popular monocle-wearing mascot who shares many traits with Pennybags (the cane, the top hat, the air of douchiness), but has two important differences:
One, he does have a monocle.
Two, he's a fucking mutant peanut.
"I'm not wearing paaaaaaaaants!"