Posted on September 25, 2013

Think penny loafers are an old-fashioned prep school look?

Rebel Alexa/ Shoes


Prep school students in the 1950s decided to insert a penny into the diamond shaped slit, the name “penny loafers” stuck and the hand-sewn slip on with the ivy league heritage became ubiquitous for collegiate cool. But in these days “penny loafers” are no longer the domain of sockless Italians or Wall Street boys as Gordon Gekko wannabes from the 80’s.


The autumn begins, now is a perfect time to wear my Alden Penny Loafers. In order to look sleek and modern with penny loafers I always wear the shoes with denim and sockless. Never with a suit because that’s too conservative.

Vassar college-penny-loafer

Vassar College Girls in Penny Loafers


Girls from the 40’s – white socks in Penny Loafer… Michael Jackson say “hello”


Bardot and the 70’s Gucci Loafer

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  • Reply Mara August 22, 2014 at 2:29 pm

    Hey, where are those pants with the big ‘patches’ from ? xx

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    • Reply Rebel August 24, 2014 at 9:21 am

      From Maison Scotch

  • Reply Jen September 22, 2014 at 3:00 am

    What size did you order your Alden shoes? I have been looking into getting a pair but not quite sure how much I have to size down considering they are men’s shoes.

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    • Reply Romantique September 22, 2014 at 4:37 pm

      Hi Jen, thanks for reading!

      I’m wearing the Alden in size 39 / UK 6. Hope this helps.


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