Dig It: Dexter Shoe Ads, ’65-’68

The 1965 Dexter ad above looks rather like a penny loafer graveyard, which is really where the  Venetian loafers below belong. Such a ghastly shoe, like a face with the eyes, nose and mouth missing. Of course, others likely feel that way about the bit loafers in the final image.

16 Comments on "Dig It: Dexter Shoe Ads, ’65-’68"

  1. Remember the good old days when you could go into any men’s shoe store and actually find something you like? These days you have to know where to go to find classic styles.
    Very sad, unless of course you like shoe styles that Alladin wears!

  2. “…as well as those ghastly Venetian loafers, which are like a face with the eyes, nose and mouth missing.”

    Could not agree more. I feel the same way about Macs with covered buttons.

  3. Funeral Pyre, 1967, They must have been inspired by….The Doors?

  4. In reality, if not in their advertisments, Dexter still produced classic loafers until well towards the advent of the current century. They only added new styles to their range, they never dropped the originals.

  5. Dexter is still carried by Payless and though their current offerings are beyond hideous, they did make a decent slip on a few years back:

  6. Payless bought the rights to the name and logo otherwise no connection.

  7. If i remember correctly, Dexter was cutting edge, well if you wanted neolite sole loafers.

  8. I like the look, but I really like the price of the 1957 Collection Tassels. I wonder what the quality is like? Anyone?

  9. http://www.shoeline.com/brand/dexter1957.asp

    They are still available, albeit in limited sizes.

  10. Love the old Dexter penny loafers.,especially with white socks.Now wear Bass Weejun penny loafers.Always looking to buy vintage ones in a size 13,John on 302-226-5505

  11. Dexter was a step down from Bass and Sebago.
    Better than most mass market shoes now.

  12. Jesse Livermore | January 7, 2021 at 4:27 pm |

    In case anyone is interested in the old Dexter property,


  13. Old School Tie | January 7, 2021 at 4:53 pm |

    Had a pair of their black wingtips back in the 1990s. Good shoes.

  14. I own two cabins on the lake in Dexter, Maine. Many of my friends family members worked for Dexter Shoe. The sale of the company to Warren Buffett and subsequent closure of the factory there was devastating to the town. Warren Buffett’s company ran the Dexter brand into the ground to the point where a once proud company that made good shoes is unrecognizable. Not a unique story but one that devastated a Maine town and residents.

  15. Down Tradden | January 7, 2021 at 11:59 pm |

    @ Old School Tie

    By coincidence, when I opened this thread, I had just dusted off a pair of 90s Dexter wingtips and two pairs of cap-toes that my housemaid wants to give to her janitor. They are still wearable. They gave me 10 years service.

  16. Old Bostonian | January 8, 2021 at 12:11 am |

    Far from being ghastly, those Venetian loafers are truly minimalist.

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