Will Cain Is Having an Midlife Shoe Crisis @​willcain debates making the jump to becoming a loafer guy, sparking a hilarious conversation on shoe choices, grow

Will Cain Is Having an Midlife Shoe Crisis @​willcain debates making the jump to becoming a loafer guy, sparking a hilarious conversation on shoe choices, growing old, and the fine line between wearing loafers and owning Hugh Hefner robes. Is it a natural evolution or a major fashion trap? [▻](htt…