Papa’s Pennies

Penny loafers: suitable for everyone, including old bearded men who like safari-hunting, sea-fishing, arm-wrestling, bullfighting and hard drinking.

Shout-out to longtime comment-leaver “Old School” for submitting this great photo. — CC

Addendum: photo info: 

“Ernest Hemingway at his standing writing desk on the balcony of Bill Davis’s home near Malaga where he wrote The Dangerous Summer.” — Life Magazine, Jan. 1, 1960.”

40 Comments on "Papa’s Pennies"

  1. Not the most manly picture of Hemingway, in my opinion.


  2. Many sides to Hemingway.

    As much as I like the Alden Leisure Handsewn Mocs, I’d like to own a couple of pairs of really well made old-school penny loafers for weekend wear. Just like (and I mean identical to) the Weejuns of old (including stitching and penny slot and so on), but a high quality leather. Oxblood calf. Not the cheap stuff the Bass folks use for their “weejuns.”

    Is Ansewn in Maine still around? I guess one would have to look to Rancourt for a custom job.

  3. sacksuit,
    Did you want him to be wearing a pink OCBD and chartreuse trousers to look manly?

  4. Is he wearing shorts or a pleated skirt? The picture would make a funny Illustration for some of the newer biographical insights into his sexlife.

  5. Sacksuit, I thought the same when I saw this picture a few years ago. His stance seems feminine but not as feminine as John Wayne’s in this famous photo:

  6. S.E., Rancourt makes a copy of the original Weejun for Sid Mashburn, only difference is the color:

  7. They’re not oxblood, but I read that the original Weejuns were offered in a shiny brown color.

  8. Hah – GS: I thought of that exact same pic of The Duke when I read that comment.

  9. I’ve always thought that wearing loafers without socks isn’t a very manly look in general. It can pass for lazy non challance on a co-ed, but on anyone over 21 it looks distinctly feminine. This photo reminds me of the incident Norman Mailer created by walking around with a poodle on a leash. Is Hemingway being just as intentional?

  10. One thing it ain’t is a great photo. I’d much rather that images like the one above and that dreadful one of The Duke hadn’t made it into print. And really, is it of any import that Papa wore loafers? I’m sure Faulkner, Steinbeck, Cheever, O’Hara and Updike wore them as well.

  11. I have four pair of early 1970’s USA original Bass Weejuns of various shades of brown (depending on how much cordovan or brown polish I applied) that I still wear. The Mashburn model looks pretty close to mine, but the stitching looks a little different and the heel panel is more curved. But overall, not a bad copy.

  12. @Frankly

    That would be more masculine than the get up he is wearing in this picture.


  13. The Cavanaugh misses several marks, including the penny slot and the strap stitching on the side.

    I like the Mashburn version, but I don’t care for the color. Prefer a true oxblood.

  14. Boston Bream | October 7, 2017 at 12:32 am |

    These comments about Hemingway’s seeming lack of a manly appearance in the photo ignore the fact that many guys think that anyone of us wearing the Ivy uniform of a navy polo shirt, khakis, and penny loafers is gay.

  15. Anglophile Trad | October 7, 2017 at 1:36 am |

    They remind me of full-cut British army officer’s shorts; nothing unmanly about that.

  16. His clothes do not look feminine it’s his stance. He has one knee slightly bent forward and looks kind of infirm. Compared to shots of him like this:

  17. Philippo Verdi | October 7, 2017 at 4:14 am |

    Poor Papa! He can’t win: either he’s accused of being too macho or of looking unmanly! Hemingway had no hangups about his masculinity and didn’t have to worry about his stance.

  18. Richard Meyer | October 7, 2017 at 6:43 am |

    Hemingway died at 60. Old man?

  19. I hope I don’t go blind after looking at the Duke. My God, how could he even allow his picture to be taken? How could he dress like THAT?



  20. Have to admit, the shorts threw me for a second first, but then I realized they appear to be a crisp, well ironed, perhaps linen. Combined with the shirt, which seems to be more of a boat neck cut….so, ironed shorts and boat neck, perhaps less feminine and more foreign by today’s standards.

    Either way, most likely worn with an authentic GTH attitude.

  21. While no EH apologist (or any Lost Generation writer for that matter) he did distinguish himself during the Great War; suffering severe leg injuries from shrapnel. Let’s be assiduous in our observations concerning his stance. That aside, yes, very feminine.

  22. Parker Bradford | October 7, 2017 at 10:27 am |

    Silver Medal of Military Valor, Italian Armed Forces (c. WWI)
    Bronze Star, United States Armed Forces (1947)
    Pulitzer Prize, The Old Man and the Sea (1953)
    American Academy of Arts and Letters Award of Merit (1954)
    Nobel Prize for Literature (1954)
    Top Reporter of the Last Hundred Years, Kansas City Star (1999)

    Far more noteworthy than his stance, I daresay.

  23. Considering Hemingway’s sense of self-presentation, that’s likely just what the alpha male wore at that place & time. And go back over a lot of the old “Apparel Arts” resort wear: laced espadrilles , onesies with ascots.

  24. Cranston Hughes III | October 7, 2017 at 1:04 pm |

    I’m glad you all have such a homoerotic idea of how he should look. Well done, boys.

  25. Well that doesn’t make sense to me at all. Soldiers expect their captain to look and act like a captain, the better to admire him.

    What I do find curious and a comment on the digital age is that Hem actually ACTED manly throughout his life, yet guys who presumably would struggle to keep up with him in his many pursuits are so quick to critique a photographic moment — one instant in the man’s life — that appears to look awkwardly “feminine.”

  26. @Boston Bream “many guys think anyone of us wearing the Ivy uniform of navy polo shirt, khakis and penny loafers is gay” Not anymore, don’t you know now it’s the uniform of the “white supremacist”

  27. There’s no denying that Papa was manly, he is the epitome of the sportsman (see picture in my previous comment) he just happens to look not like his usual manly self in this picture, that is a fact. And it’s not the clothes.

  28. If Hemingway can be caught by the camera looking unmanly, imagine what it’s like for all of us.

  29. whiskeydent | October 7, 2017 at 3:00 pm |

    I just think he looks happy here, which I assume was a rarity in 1959. Late in his life, he was in a lot of physical pain from various injuries (war wounds and a couple of plane crashes in Africa, I think).

    Regardless, Hemingway would not have given a damn about what any of us think about the photo.

  30. @Christian

    I was going to comment similarly. I’ve had to say “please delete that” (mostly to the wife) on more than one occasion where I’ve been candidly photographed while striking an unaware and awkward pose. As we age I suppose our self-consciousness will probably soften.

    Recently rewatched Ken Burns Civil War doc and was struck by how familiar the soldiers seemed in many of the group photos. Some of their poses would be completely suspect if set against today’s standards of masculinity.

    This one in particular:

  31. Responding to S.E,’s original query – Check out the AE Kenwood. Rare classic details including full beefroll and pinking, and it comes in “burgundy.” I have them in brown leather, which seems no longer available, for exactly the kind of weekend wear you describe. They’re quite nice.

  32. Hemingway is wearing classic 1950’s men’s shorts — high rise and full cut. Take a look.

  33. Not a fan of the beefroll.

  34. the best reproduction was the McNairy version. The burgundy/oxblood. Nothing like it since. Guessing that shoe was made by Highland/Ansewn, which I think no longer exists.

  35. Jonathan Sanders | October 8, 2017 at 9:01 am |

    The big takeaway from the photo is that he always projects perfectly the worldly american archetype. He’s clothes are always in the moment of his place, activity, etc. Nothing is ever clever or ironic. And the only go-to-hell quality of his choices shows how comfortable he is in his own skin; not just his clothes. The end result is that he looks like the Most Interesting Man in the World. Give this guy a Dos Equis!

  36. Re the comments about Ernest Hemingway’s supposedly feminine pose in the photo, Hemingway’s youngest son, Gregory (nicknamed “Gigi” (?) as a child), despite (because of?) having four wives and eight children, was a transgender individual:
    “When (Gregory Hemingway) he was arrested just days before his death, he first gave the police the name Greg Hemingway, then changed it to Gloria.

    Hemingway died October 1, 2001 of hypertension and cardiovascular disease in Miami-Dade Women’s Detention Center. That day, Hemingway was due in court to answer charges of indecent exposure and resisting arrest without violence…

    In most obituaries, he was called Gregory, but Time magazine published a brief notice of the death of “Gloria Hemingway, 69, transsexual youngest son turned daughter of novelist Ernest Hemingway” and noted the novelist once said Gregory had “the biggest dark side in the family except me.””

  37. @GS

    Your last comment was spot on.


  38. michael powell | February 4, 2021 at 1:36 am |

    I’ve had exactly two pairs of penny loafers. An olive pair in the early 70s; and the oxblood pair I have today. It’s the perfect accessory with a blue blazer and khakis.

Comments are closed.