Weejuns Go With Everything, 1940


This image (another find by comment-leaver Carmelo in the Esquire archives), came with a date but no caption. So I decided to give it one for the headline above.

It’s easy to think of penny loafers as a casual shoe since, in the grand footwear scheme of things, they are. But much of the charm of Ivy-preppy dressing is the mixing of casual and dressy items. The postwar legacy of the Weejun is that it is a shoe to be worn with khakis and a blazer, or sockless with a madras shirt. But in the Weejun’s infancy (it was introduced in 1936), when men still wore hats and gloves and overcoats, the shoe was able to hold its own among these more formal sartorial items.

So if you’re looking to put a new spin on the old staples in your wardrobe, try this. Next time you put on that winter topcoat and hat, don’t reach for the tassels or lace-ups. Penny loafers did the job just fine before the war, and they can do so now. — CC

22 Comments on "Weejuns Go With Everything, 1940"

  1. Father Brown | December 7, 2015 at 2:24 pm |

    Although it might very well look nice, waring a winter top coat and hat typically calls for a more robust shoe in my ‘umble.

  2. Father Brown | December 7, 2015 at 2:25 pm |

    Sorry! I me at to type “wearing”, not “waring”.

  3. I’m digging the reversible trench coat.

  4. While I find that your typical brown weejuns can be a bit off at times I’ve found that burgundy ones go with literally everything. They can be worn with all but the most formal of attire. I wear them with everything from the most casual summer outfit all the way through to a three piece suit.

  5. OK Father Brown, but you understand that the point of the post was to reconsider that very notion?

  6. Roger C. Russell II | December 8, 2015 at 3:06 am |

    I wish Bass made a shoe as substantial as the one pictured in the add. I miss my Weejuns from 30 years ago. I wore them with just about everything.

  7. When and why did men stop wearing overcoats?

  8. stevemcgee99 | December 8, 2015 at 2:11 pm |

    Looks to me like the guy with the coat has lace-ups.
    And at that time at least sport coats were casual.

  9. @Christian

    Of course I get that. Don’t get me wrong, I didn’t miss the point. Aesthetically I think it *looks* pretty cool… However from a practical point of view, I find cold, soaking-wet ankles and feet mildly uncomfortable(especially with the amount of snow we’ve been getting here in the Hub the last couple of years. No matter how good they look tous ensemble with the above-mentioned ensemble, the lack of practicality makes it a no-go for me.

  10. @Ivy Novice: Where do you live that you don’t see men wearing overcoats?

    Are you in Florida, perhaps? Louisiana?

    When it gets cold enough, people certainly do wear overcoats.

  11. It’s possible to wear a coat, hat and gloves when there’s no snow on the ground.

  12. Father Brown | December 8, 2015 at 4:59 pm |


    Touché, sir.

  13. I have a good inclination that Pere Noel is brining me a pair of Alden’s cordovan slip ons this year. I bought 2 pair of bass kiltie tassels several years back, caveat emptor! They hurt my soles.

  14. And hurt my eyes.

  15. Zing! Yes, they were the result of a dreadful BOGO 50% outlet mall impulse purchase.

  16. Weejuns with a suit? No way.

  17. Henry Contestwinner | December 9, 2015 at 3:50 pm |

    A hat like the one Mr. Holden is holding in DCG’s link is my new go-to hat for summer. I used to be a Panama man, and still like them, but the greater texture and color of a hat like the one in the picture adds something to the light solids that predominate in summer clothing.

  18. Henry I spent the whole summer looking for a hat like that in my size, no dice. Coconut with a madras band. Maybe Santa will have better luck!

  19. Henry Contestwinner | December 10, 2015 at 12:20 pm |

    DCG, my current coconut straw hat is a “Madrigal” from Stetson, which I purchased at Portland’s best haberdasher, John Helmer (now in its third generation of family ownership). A quick on-line search revealed more from other vendors. I’m very pleased with my Stetson, more so than my previous purchase from a different manufacturer.

    Coconut straw is brittle, so hats made from it require more careful treatment than Panamas do. In order to prevent the top crease from breaking—which is what ruined my first coconut straw—run a thin line of Elmer’s glue around the inside of the top crease.

  20. @ DCG: I have a coconut straw hat with a madras band from Miller Hats that I would recommend. I love wearing it with everything from short sleeve shirts to my old Brooks Brothers poplin suits. I have owned it less than a year so no idea of longevity but it feels like quality and the price is such that one could replace every summer and not break the bank.

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