Revisiting The Penny Loafer


Most folks would agree that when you think of penny loafers the first thought that pops in your head is the legendary Michael Jackson. Michael is known for taking this classic shoe, reinventing it and making it his own. Not only did he create a style craze with the loafer back in 80’s, the shoe became his dancing staple. His longtime designer Michael Bush explained how he chose and designed what he wore.

Clothing is like a canvas; it explains people’s personalities. Michael was extremely shy on a one-to-one basis, but with his clothes, it was always about, “Look at my clothes, not at me.” Most of all, Michael really understood showmanship. He always said, “I dance the beat and the clothes have to show the beat.”

From working with Michael, Bush learned that he preferred to dance in Florsheim shoes:

Those are the shoes that his family could afford when he taught himself to dance. Everyone thought he should have custom-made shoes, but he said to me, “Do what you want with my clothes, but don’t touch my shoes. I’m a dancer, that’s my art form.” I remember once, in Japan, a manager came up to me and said, “These shoes look like hell, polish them.” So I did and handed them to Michael, who didn’t get mad but told me, “Listen, Bush, if my heel slides off the back of the other heel of my shoe and I get shoe polish on the bottom of my sole and fall down on stage, we are all unemployed.” For the next 21/2 years, during the “Bad” tour from 1988 to ’90, I slept with those shoes under my pillow for fear of someone else polishing them. I never let them out of my sight.

GQ magazine has created a daily fashion visuals on Instagram called What to Wear Today for each day of the month.  Author Liza Corsillo gives advises on how to reinvent some MJ inspiration to your wardrobe to turn this shoe from plain to your wardrobe’s secret weapon. She writes:


“The trick to turning these penny holding slip-ons into badass style grails is all in the context. First, pick up a pair in all black rather than the traditional chestnut brown. Next, go a little rocker goth with the rest of your clothes: black jeans, black leather belt, white tee, black and white bomber jacket, and a slicked back hair do. You’re going for two parts rockabilly, and a thousand parts style god. Last but certainly not least, wear your new loafers with a pair of plain old white crew socks. It’ll add a touch of Michael Jackson attitude and a slide in your step.”




Where to get the items pictured above:

Saint Laurent, $2,390, available at Buck Mason, $28, available at Acne, $215, available at Filson, $58, available at John Lobb, $1,300, available at Hanes, $18, available at

Here are a few more styles of penny loafers worn by Michael:


Deer Stags –  The slip-on dress shoe is made from a genuine hand sewn moccasin construction with a supple kidskin leather upper. It also provides a hidden elastic gore for added comfort and flexibility, a fully cushioned foot bed, and leather linings from heel to toe. It seems to be a popular shoe for MJ impersonators.


Bass Weejuns – Michael wore first wore a pair of black G.H. Bass Weejuns styled with his signature white socks for the 1983 “Thriller” video, and rocked them countless times after that iconic moment.


Sebago Cayman – The Sebago Cayman flat strap penny loafers and signature Fedora worn by pop icon, Michael Jackson at his ground breaking Madison Square Garden concert in September 2001 was sold at auction on December 16, 2009. The shoes that are each inscribed with the words ‘Rock My World Billie Jean’ on the sole went under the hammer at Bonham’s Auction House in London. After a fierce bidding war, the lot went for a staggering sum of $37,343 to an unknown bidder.

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