Give an Ivy Classicist the rules about when and where to wear sneakers and they are shod for a day. Make the rules together and they are shod for a lifetime.

That’s shod – twice in one paragraph. Hang on. YES. It means what I wanted it to.

Let us begin the session with common ground. These are the universal applications of sneakers:

Gym class through high/prep school.

In my high school days, the shoe was Nike. These are from 1979, and I remember them. I also remember that Nike was the first sneaker brand you had to have. The others at that time, Adidas, Puma (Clydes, Puma Clydes may be the coolest sneaker ever shod – AND I got shod in again). All good brands, but Nike you had to have if you wanted to be a serious competitor. Or in my case, if you wanted to be perceived as a serious competitor.


On any court.

If you were a stand up comedian in the 90’s.  On a boat.  When you are with Dylan.

Ok, the rest is gray area.  I remember one of the first illustrations of Ivy I ever saw was this:

If you are new here, and three quarters of you are (wait, is that math right, if we have quadrupled readership in a year, then… yes, right?) then you have not seen this image before perhaps. It was the banner on the FB Group page for forever. Now we change them out every week, but this was wallpaper for over a year. I related because the guy’s beard is gray, but also the sneakers.  It is also on an old post on this site.


Those are sneakers with a bow tie.  This position was formerly “endorsed” here.  Not on my digital legacy.  Here’s why you don’t want to do that.  The campaign to have bow ties taken seriously again is countermanded when you wear sneakers with them.  If YOU aren’t going to take bow ties seriously, and you are wearing them, why should I?

In fact, as I get older (which is occurring at a geometrically expansive rate now that my daughter is in high shool) I can’t wear them with a tie, even.  Can you?  No, you cannot either.  These are prickly thorns, especially coming from Joe Degage ova heyuh.  Ivy is based on irreverence, but like anything else, if you are laughing at a joke three times as loud as anyone else in the room, you probably don’t get the joke.

For further clarification, let’s consult the masters.

Himself in sneakers on a boat. You can wear sneakers with a bomber jacket on a boat. But what you cannot do is wear them with someone who has time travelled from the future to be on theboat with you.  That’s allegedly Peter Lawford.  Yeah.  If Peter Lawford was born in the 90’s.   There’s this whole school of thought about UFO’s now that says that they are really drones and that the government is classifying them as UFOs to hide technology we already have.  I dunno about that, but I do know those sunglasses didn’t exist then. 


Another classic:


This time no Men In Black. I always wondered if Jackie hated him in sneakers.


So the rule here – with khakis as long as there is no tie, yes.  Even with time travelers.

You can rule out a lot of options for sneakers with one simple visual representation.

This image was also used in an article about how to wear sneakers with a suit. I respectfully submit (1) you can’t (2) that’s not a suit.


For your consideration:


Ok, we have used Mr. Newman as an Ivy checkpoint for years. He and Mr. McQueen. Yet. Here in sneakers and Ivy, a perfectly acceptable combination… but for the pinky ring and the bracelet. I wear bracelets. They are always string or paper, except for one leather one that a family member gave me with the name of my tour on it. This bracelet, and others I have seen on Mr. Newman, of whom I have the highest respect (let me know if you need me to tell the Paul Newman story again), are always these metal things. Does that disqualify one? Regardless, the sneakers are on point.


We’ve drilled it down.  Never with a suit, always on a court, and always wear a suit to court.  Any time with khakis as long as there is no tie involved.   Never with a metal bracelet (sorry Paul).






34 Comments on "Sneakers."

  1. Whomever styled the young guy in the blue suit knew what the hell he was doing.

    The only acceptable sneaker for a man to wear outside the gym is a Common-Projects-style white shoe. This outfit is modern ivy(making a formal ensemble more casual) for various reasons:

    1. The suit is worn with a casual band collar shirt.
    2. The trousers are cuffed.
    3. The socks coordinate with the suit.

    The overall aesthetic (I know people hate that word) is minimal, clean, and fresh.

    Technically, it is not ivy, but it incorporates the casual-while-formal/dressed-up-when-casual dynamic Christian Chensvold pontificated a few years ago.

    • Agreed. Not a look I would go for myself, but definitely in the ballpark of an acceptable “dressed-down” suit. It looks sharp, though I do agree that trainers with a suit does not work, as a general rule for amateurs.

    • John Burton | June 24, 2022 at 6:26 pm |

      Those pants are hugging his calves like they were the last part of a sinking boat above water. That suit is shinier than a lighthouse. And the fact that he took a look at that suit and thought, band collar. You know what goes with caviar? It ain’t Oreos.

  2. Philly Trad | June 24, 2022 at 9:59 am |

    Converse low-top white (or navy) Chuck Taylor sneakers are retro enough to be worn with khakis. I can’t imagine wearing any other sneakers.

  3. Hardbopper | June 24, 2022 at 10:07 am |

    1. I believe “sneakers” are the best boat shoes, and I have my preferred make and model. They just work.

    2. I remember that old post and the image. What immediately strikes me, every time I see it, is that it looks South Parkish.

  4. Charles bellinger | June 24, 2022 at 12:12 pm |

    Gray canvas bobos for most everything. That being said for sneakers sneakers I’ve obsessively worn puma whirlwinds for decades and pick up any used pair in my size since they were discontinued several years ago

  5. Those glasses were avant la lettre but they did exist – here’s another picture

  6. Bruno '79 | June 24, 2022 at 3:16 pm |

    I just returned from the Rhode Island Bar Association Annual Meeting. While waiting for the seminars to begin, I spied my brothers’ choice of footwear. They fell into three groups:
    1) square toed black shoes (like the king Lou Groza wore to kick field goals);
    2) sneakers (both the gym variety and the hybrid shoe with sneaker sole);
    3 boat shoes. I was the lone, suit wearing tassel loafered person in sight.

    • John Burton | June 24, 2022 at 6:29 pm |

      I mean, that is sad, but lawyers wear suits all week when the rest of us can skip so maybe it is just a break. Still, the square toed black shoes are indictable.

  7. whiskeydent | June 24, 2022 at 4:00 pm |

    I have long and narrow feet, so Allen Edmonds is my go-to brand. I recently noticed that 1) AE was showing those godawful hyybrid type shoes in the Dress Shoe area 2) almost all had that thick, white sole that just looks like a deck shoe on steroids 3) the ones lacking the thick white sole had plastic-looking sorta-outdoor soles 4) AE even made one in cordovan leather 5) yes, cordovan leather, and 6) AE had eliminated many of its truly Dress shoes.

    As is my wont, I fired off a snarky and snarly email that, amazingly for me, had zero cuss-words. I did call into question the intelligence of the company’s executives and the sanity of its designers. Most importantly, I screeched at length about my loyalty and their betrayal.

    I got back a short note saying they were sorry I was upset. No explanation whatsoever, no BS about style trends or some-such crap.

    This proliferation of stupid, white-soled hybrid shoes is a national security problem in my rarely humble opinion. I want to marshal all the powers of every one of the government’s alphabet agencies in this battle. Make. It. Stop.

  8. AtlantaPete | June 24, 2022 at 5:19 pm |

    I have been wearing white (preferably scuffed up) canvas sneakers since the late 50s (I am older than dirt) only with khakis or with shorts sans socks. When I started weawring them in high school, all that was available in my mid-size Midwestern town were Keds. My high school was divided into the college bound and those who wore FFA jackets and would be working in agriculture with the result that I was constantly badgered about wearing “girl’s tennis shoes.” By the way, the wealthist guy in my class was an FFA guy who didn’t go to college, but ended up owning mulptiple grain elevators.

    • AndrewK247 | June 24, 2022 at 8:25 pm |

      When I was growing up on the NW side of Chicago, there was no choice regarding scuffed/non-scuffed. When a kid would show up to school with new spanking-white gym shoes, a group of other kids would surround him and step on his shoes until they were sufficiently scuffed. Will admit to being on both sides of that equation.

  9. Yes, please.

  10. G. Ellery Cobbold | June 24, 2022 at 7:29 pm |

    I wear white Doek Oxford sneakers. Pricey but extremely well made and comfortable as heck. They look good with an old pair of Bills, an old surcingle belt, an old Mercer OCBD, and an old J. Press bucket hat.

  11. AndrewK247 | June 24, 2022 at 8:15 pm |

    With regard to the Facebook banner, you forgot one variable:
    Old guys can wear whatever the heck they want.

    Aside from that I agree gym shoes do not go with ties and suits.

  12. MacMcConnell | June 24, 2022 at 10:43 pm |

    Converse All Stars were for gym class. Jack Purcell was for tennis and all around wear along with Us Keds, similar to Newman’s. I still wear Purcells and Adidas original Stan Smith. I have always worn white tennis shoes with khakis, blazer and tie.

  13. Sperry, Tretorn, Stan Smiths and K-Swiss were the preppy sports shoes of my younger years. Still wear a pair of grey slip on Sperry canvas shoes. I’ll don a pair Black Adidas Sambas with jeans on occasion and Brooks running shoes for exercise.

    Agree with the commenter about Allen Edmonds. I wear an !!.5B and their Verona bit loafers are a godsend. I have them in black and brown.

  14. Frederick Johnson | June 25, 2022 at 12:34 pm |

    Jack Purcell’s but only with unironed, uncuffed khakis.

  15. Yes to Adidas Samba — black w/ white stripes.

  16. William C Kazak | June 26, 2022 at 2:32 am |

    Back in the old days, in gym class, I wore black Chuck Taylor All Stars. That was before the insides were made softer.My first year of college was in SoCal. I stayed with my Aunt and Uncle, her two sons and one daughter. That is where I learned about Sperry CVO canvas boat shoes because my cousin had them. He also had the brown leather Sperry boat shoes and a tan pebble grained tan colored thick sole shoe. Impressed me so much that when I got back to my parents in Illinois, I had to duplicate all three.

  17. NaturalShoulder | June 26, 2022 at 7:52 am |

    I love my tretorns.

  18. Roger Sack | June 26, 2022 at 3:44 pm |

    In my university years ( Cornell) during the “Golden Age” I witnessed and participated i
    n the transition from dirty white (or tan) bucks to tennis shoes, usually white, sometimes blue,
    ideally Tretorns. Tennis shoes were often rotated with penny loafers and even desert boots.
    When it was frigid and snowy, which was often, all manner of military surplus, hunting boots,
    and even “engineer boots”a la “Hells Angels” were worn by the very Ivy/prep students.

  19. I’ve always found the regular lace-up Vans (the “authentic” model, or the similar “Era” model that has the padding around the ankle) to be a classic CVO shoe. They come in every color possible, they are usually cheaper than the Sperry version, and you can cut off the little white nametag if that sort of thing bothers you.

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