The terms ‘penny pincher’ and to ‘pinch pennies’ came about at roughly the same time but with slightly different meanings. A “penny pincher” is thought to be miserly while someone who chooses to “pinch pennies” is thought of as being thrifty.
The more positive version of the term “penny pincher” was first recorded in 1942.
In June 1943, cartoonist Harry Haenigsen created a new cartoon character, Penny Pringle, and debuted it in The New York Herald-Tribune. It became his most successful cartoon strip of all the strips he had in syndication.
Penny was never gawky or shy and others saw her as confident and self-assured. She was a no-nonsense kind of girl which mystified her cartoon parents, Roger and Mae Pringle.
And, you guessed it, on top of all that, she was thrifty … always pinching (saving) her pennies and doing the smart thing every step of the way while staying current and popular with kids of her day.
Historically Speaking 