I was intrigued with meeting Michael when his sister told me how stylish her brother was. After finding some time, I asked if he would be interested in being featured and so we met up on a late summer evening near the Financial District where I used to work. It was certainly interesting to see Michael walking through an area where most men paired suits and dress shirts conservatively. I like how he adds small personal touches to make his ensemble unique such as the bird clipped to his lapel and lodging pennies into the cutout of his loafers, which prompted to ask why they’re called penny loafers.
According to a few sources, penny loafers were designed by John Bass in the 1930’s and originally called Weejuns. When pay phones were still ubiquitous, Weejun wearers start placing dimes – the price of pay phones in those days – into the shoe pocket to make emergency calls. Pennies later came along as when students wishing to make a fashion statement took to inserting a penny into the diamond-shaped slit on their Weejun instead.
It was interesting to see a fashion statement such as inserting pennies into loafers have a history and it’s almost comical thinking it now because pay phones has now become so obsolete. While chatting on our walk back to the subway, I expressed interest in purchasing a pair of boat shoes and Michael exclaimed that I should get loafers instead because everyone had a pair of boat shoes. His mindset was different and that’s what I liked about it.