Just ask the two Chicagoans who founded Cole Haan, known for making some of the best shoes around like the now iconic ...

a logo tucked inside a penny slot, a lug sole and a shock-absorbing footbed. "My inspiration for this loafer was mainly from 1950 and ‘60s Ivy league style," Fujiwara said in a statement.

The men's burgundy penny loafer is the perfect fall transitional ... And because some things will always be in style, we’d like to reaffirm our commitment to this most classic of dress shoe ...

First up, there’s penny loafers ... Oliver Cabell is the designer to know. The Ivy League-coded top stitching and low profile make these loafers one of the brand’s more statement takes.