Two Guys Who Write About Ivy Walk Into A Bar

This is two guys in an Ivy League bar, but unlike how-do-you-like-them-apples Mr. Diamond and I agree on a whole bunch. The dirtbag thing not so much, but read on…

Well well well.  It does seem that our sails are catching some wind, yes?  The flurry of Prep Is Coming Back (damn with the Prep thing but we can get to that too) articles that line up with our jam is gratifying.  I could review one a day, but this one is particularly good and also thought-provoking.  It is in GQ (relax) and is written by Mr. Jason Diamond.  Within minutes of its release my email thing started chirping, and I read it, and wrote Mr. Diamond right away.  And he answered right away.  We did a few emails back and forth over a few things, and it ended up with my last email to him reading:  “You, sir, are Ivy.”

Here’s the article.

Let’s get the title out of the way.  It was my first objection.  If you are part of our FB group, and if you are not you should be, it is the best curated and most engaging group of its kind on FB, even when they shut down, if you are part of our group you know that I have been riding the idea of (1) needing to understand the history of Ivy and then (2) needing to understand and master the rules and then (3) needing to assemble the basic elements and then (4) combining the basic elements with culturally relevant pieces of your own to create a style I call (thanks Evan) Degage.  And I have been saying that this is the future of Ivy.  The uniform stands, always will stand, is eternal and is not to be effed with in any way, shape or form.  But modern life makes it hard to wear the uniform every day, and in order to perpetuate the aesthetic, we have to let it breathe, let a new generation have at it, and see what happens.  What happens is Degage.

It is not dirtbag.  So my first thought to Mr. Diamond was, what’s with the dirtbag?  His answer was off the record (not because he asked for it to be, because I asked him on the record questions and this wasn’t one of them) so you are gonna have to trust me on this:  there is a legit albeit a little bit into the weeds reason for his use of the term.  And we can leave it at that.

With his theme, Diamond is spot on.  And he is a damn good writer.  I asked him three questions, to consolidate all the thinking, and he was kind enough to really dive in. Here’s the first question, and his (edited) first answer:


  1. Ivy and Prep are in fact kissing cousins, but kissing cousins that live far part.  Ivy was born out of rebellion, in much the same way that you talk about rebelling now, but with the important caveat that rebellion works WITHIN the system, and that the pillars of that system (education, work ethic, the value of thought, innovation of old ideas, etc.) are as important as anything else.  If people pick and choose an OCBD here and a repp tie there, are those values reflected and communicated? 

I’ve personally always seen it more as prep was maybe more the evolution of Ivy. The kids I was hanging out with wore their dad’s old shaggy dogs when it got cold or would toss on an old OCBD with patches and stitches to do yard work, but they were also wearing Air Jordans or Chuck Taylors or baggier chinos or whatever. But it wasn’t a thing…if that makes sense. It was just them pushing the boundaries a little.  I spent a lot of time trying to understand the subversiveness of looking one way when you’re supposed to look another. It sounds silly, but even the act of going to a hardcore show in an old Lacoste polo could be seen as off or weird, but I didn’t care. I’ve always been of the mind that what we consider the “preppy look” is really just the work of good marketing and a very funny satirical book that came out the same year I was born. The same could really be said of Ivy or any look connected to some subculture, whether it was working class kids in London or old-money kids in New England. I personally feel like it’s all the same, and I 100 percent know and understand why people would disagree with that.

The act of picking any piece of clothing up has to have intention beyond just getting something new to wear. As long as there’s intention and thought and the understanding that how you dress is an individual act then I think the values do come through — at least to me they usually do. That’s why I’ve personally always had an appreciation for the sort of looks we’re discussing.

And he’s right to a large degree.  At least up here where we rake leaves.  While I say that Ivy was born of rebellion, evolved into conformity and then like everything else in the circle of life came back around to rebellion, Diamond’s observation that a lot of Degage comes from… just, life and not making a statement is a good one.  There are leaves to rake, and this is what is hanging on the hook.  Anyway, here’s question #2 (edited again, this is a blog, not a term paper)

2.  The process you and I both describe, individualization of trad elements, has been around for awhile and it can be argued is the origin of Ivy.  What’s different this time?

The obvious answer is always going to be the Internet. But there is the factor of time and also, I hate to say it, the politics of the day.  One of my heroes, the late Glenn O’Brien, went to Georgetown, wore ties and blazers and looked fabulous in tartan, but he was also as important to bridging the NYC art scene with punk and hip hop as nearly any person I can think of. I don’t think anybody would call him a preppy, but on paper he had the credentials of one, I’d say. I’m not so sure that you could get away with that at this current moment in time, to be honest. Because while we’re such a plugged-in culture, we also tend to lean heavy on the reactionary and know-it-all side of things, unfortunately. When most people are presented with something like a man in a nice suit, those people could draw 1,000 conclusions about that person, and there’s a chance all of them are wrong. There’s always been stigma surrounding certain clothing, but I think these days, if people get the feeling that you’re rich or “elitist” or draw any conclusions based on the way you’re dressed, it could stick you with a metaphorical stench you maybe don’t want. That’s unfortunate, but these are weird times. I don’t know if it will last, and I certainly hope it doesn’t. But if it does, then it only reinforces the idea of some of these looks being rebellious.

Yes.  And no. Well, yes, if you read this sentence correctly: “it could stick you with a metaphorical stench you maybe don’t want.”  Maybe is the operative term.  I would add that I DO want that stench.  In fact, it is what I trying to create.  The idea that not everything that existed a few years ago needs to be moved on from in order for us to progress, that values can be classic in that they can stand the test of time and that maybe I was smart enough to pick up a few things from those who have gone before me – if that is a stench, let me pour a quarter-size dollop into my palms and rub it into both cheeks.

But Mr. Diamond is right, these are weird times, and some of the things we have aimed for are not as desirable anymore, and I think that may be for the good as well.  As long as I can wear a repp tie while I shift gears.  The 3rd, edited, question:

3. One of my working theses is this: the self-expression that was being communicated wearing suits and ties to work was that I belong to something, that I am to be taken seriously, and that I take myself seriously.  If the workplace is no longer the place to communicate that, it spills over socially.  Which tips us into the alternate universe where people dress more formally socially than they do for work.  Do you see that tracking yet, and what do you think about the premise?

I do see it tracking. I also see it as part of an unfortunate continuation of our declining values. Not necessarily suits only, but a decline in caring about what we wear and overall presentation, and also how we view our fellow human in some ways. This is a whole larger conversation and I feel like I’m probably preaching to the choir here, but it’s just the whole idea of putting even a little effort into getting dressed.  The guy gassing up your car, for instance. Just look at pics of him in the ’40s or ’50s. He was dressing up. It was a uniform, but it looked good, there was a presentation of seriousness involved that we just don’t have today and that’s unfortunate for a number of reasons, one of them is that it shows the expendability of individuals to companies. Just give them a polo shirt that doesn’t fit anybody right that has the company logo on it and put them to work for a low wage is the idea.  Look at pictures of Robert Caro. The guy gets dressed in a shirt and tie and blazer to go work alone in a little office by himself. If he dressed that way in a newsroom I think people would think a grandpa got lost and wouldn’t realize it was the foremost biographer in America. And when you consider the changing social norms and conversations about things like gender and people getting paid a fair wage, the idea of “the man” in a suit does feel like it doesn’t totally fit these times.  I personally think we’re going to see an even looser interpretation of dress codes whenever we are fully back to some semblance of normalcy, but I also realize it will be a case by case basis. I don’t expect lawyers to start showing up to court in shorts and a “I’m With Stupid” shirt on. But I do think office dress culture is going to radically change. And whether you want to wear a suit or not will often be up to the individual. And I think if you want to wear a suit, you will go out of your way to make it your thing. To borrow a quote and idea from another strain of sartorial subculture, my friend Nathaniel Adams wrote in the intro of his book I Am Dandy that the people he documented had “one common, beautiful, purple thread” that tied them all together. And that was “A sincere belief that elegance is paramount and mediocrity is a fate worse than death.” I’m no dandy. Not by a long shot. But I like that sentiment. As long as you’re going out of your way to not be mediocre when everything is so bland and homogenized, then I think you’re doing fine. It really doesn’t matter what you wear or how you wear it.

I have a few years on Mr. Diamond, and I may have less nostalgia for the way things were than he does, but I do say this:  his understanding of how the style will survive by evaporating some of the rule book and letting a person do their own thing – that resonates.  I prefer Degage Ivy to Dirtbag Ivy, but we both prefer to see the style live and breathe, and stand for something.

  • JB

29 Comments on "Two Guys Who Write About Ivy Walk Into A Bar"

  1. Father Brown | October 7, 2021 at 12:57 pm |

    Please, Dégagé, not Degage.

    I dunno. That looks like Jordache’. JB

  2. Evan Everhart | October 7, 2021 at 2:58 pm |

    Number 1, Engage!

  3. whiskeydent | October 7, 2021 at 4:08 pm |

    How about this: Free Ivy

    The verb, adjective and adverb.

  4. RIchard E. Press | October 7, 2021 at 5:24 pm |

    Went to prep school during a time most of my boarding school compatriots dressed Ivy. Preppie? Gimme a break.

  5. Maybe the best piece I have read in years on the subject. Motivational in an odd way.

  6. Father Brown | October 8, 2021 at 12:39 am |

    No such word as “degage”. It’s “dégagé” in English as in French.

    There is. I coined it. Kinda. – JB

  7. Ken Sprague | October 8, 2021 at 12:57 am |

    I had to look it up in My Merriam-Webster Collegiate Dictionary.

    dégagé ·
    1 : free of constraint : nonchalant ·
    2 : being free and easy: “clothes with a dégagé look”

    I like it.

  8. William Cochrane | October 8, 2021 at 1:43 am |

    Hmmm…reading both the post and the question and answers what I keep coming back to is that we are talking about the future and this style is seen as a living vital thing. As such, it is open to change. Styles only become rigid with a bevy of self appointed experts when they are dead. I’m not actually dead yet, and my wardrobe, although wearing thin and fighting a never ending battle against time and moths, is holding its own. There is room and invitation for change and innovation. I’m glad to see a swing away from the position that there is a “right” or “wrong” look. Keep up the good work!

  9. George T. Snoothound | October 8, 2021 at 8:26 am |

    @ Richard Press — Preppie/preppy is documented in use at prep schools around the same time you were in prep school yourself. You may not like the word, but it’s a real word.

  10. @George T. Snoothound —
    Re: preppy/preppie.
    It may be documented in print, but we didn’t even describe the clothing/style as Ivy.
    We said Ivy League. Certainly never preppy.
    Later on, I only heard it used disparagingly by beatniks/hippies.

  11. “Modern life makes it hard to wear the uniform every day.”

    Nothing is easier than chinos, penny loafers, and an OCBD. That’s three-fifths of the uniform right there. If you’re worried about folks thinking you’re on the way to stock up on tiki torches, Self Edge will sell you the Rick Owens Special–black jeans, black “overshirt” (whatever that is), and black sneakers–for only $2780.

    “[I]n the ’40s or ’50s…there was a presentation of seriousness involved that we just don’t have today and that’s unfortunate for a number of reasons, one of them is that it shows the expendability of individuals to companies. Just give them a polo shirt that doesn’t fit anybody right that has the company logo on it and put them to work for a low wage is the idea.”

    The school at which I teach requires male teachers to wear blazers and ties. We work for absurdly low salaries relative to our degrees (many of us have PhDs) and experience. We tend to resent the ‘presentation of seriousness’ because we’re white-collar workers getting paid an hourly worker’s wage.

  12. @George T. Snoothound: Understood re: prep/ preppy, I guess, but as someone who shares alma maters with Mr. Press (albeit decades apart) I can tell you that I rarely, if ever, heard the words mentioned. Seemed like more of an outside construct, both pre/ post internet.

  13. George T. Snoothound | October 8, 2021 at 1:42 pm |

    All I’m saying is I’ve seen it used in the 1950s by and for students in the same prep school world as Mr. Press etc. was in. Not widespread, but not simply an outside invention either. There’s some nuance to it, maybe, rather than being black and white

  14. J.G.

    Had to look up Self Edge and Rick Owens. Gee, thanks. I wish I had the last five minutes of my life back.

    Also, and I am not trying to be a smartass, what are you planning to do about your resentment regarding hourly blue collar wages? Life is too short for resentment.

    Get action,


  15. You say degage, I say d’gage’
    You say Preppie, I say Ivy,
    Let’s call the whole thing off….
    Uniforms are for people with dubious motives.
    “I say, beware of all enterprises that require new clothes, and not rather a new wearer of clot
    Henry David Thoreau

  16. whiskeydent | October 8, 2021 at 2:14 pm |


    Oh, so you have no resentments? Yes, I’m trying to be a smartass.

  17. whiskeydent

    Not really. It’s not worth the time or energy.



  18. @sacksuit

    Sorry to have inflicted Rick on you.

    I wish I weren’t so resentful. You’re right; it’s a problem. I love teaching English–it’s a privilege to make something like a living reading and talking about Shakespeare and Milton and other greats–but hate the way private school boards and administrators treat and pay their teachers.

  19. J.G.

    I’m happy for you that you love your job. I think few can make that claim.


  20. @sacksuit/Will

    That’s kind of you to say. Thanks.

  21. Marshall Sprague | October 9, 2021 at 1:18 am |

    I hope that one day you realize that talking about Shakespeare and Milton and getting paid peanuts isn’t enough and you’re able to get your revenge on the pigs who are exploiting you.

  22. Good post by JG. The first paragraph hits it. In my 30s my friends who were coaches lived in sweats and asked me why i “dressed up” in khakis. That was in the South. Now in the mountain states area, everyone I know live in jeans with silly hooded T shirts or pullover zip ups, think neckties represent one of Dante’s circles, and ask why I “dress up” in khakis.

    And we all owe a debt to teachers. And loving one’s job is a true blessing. I pray the young men in your care at least see how a man should dress from you, and the young ladies do the same.

  23. @JDV

    Thank you. Very kind of you.

  24. JDV,
    remember the days when the only “adults” in jeans and t-shirts or hoodies were waiting in line at the unemployment office.

  25. A brisk, bleak and breezy morning on the beach at the bay with the dogs. Old RL khaki cut offs, ancient white polo shirt and navy drifter sweater. A beautiful day the Lord has made.


  26. Whatever we call this (Ivy/ trad / preppy), there will be pockets — here and there, every now and then. It goes without saying that the look will survive (maybe thrive) among the more traditional, but since traditionalism is taking a beating these days, it makes sense that the style is becoming more-and-more a minority voice.

    Which, to repeat, is fine. Isn’t it? If everybody was wearing what we like to wear, the style (we) wouldn’t be unique. And being unique is interesting-and-fun.

  27. Boston Bean | October 11, 2021 at 2:41 pm |

    I fully agree.

  28. @Marshall Sprague

    Better the pig you know….

  29. John W. Matney | October 30, 2021 at 8:40 pm |

    JDV. I live in Asheville NC and just can’t bring myself to wear jeans and a sweatshirt unless I’m doing yard work. There is a shop selling traditional menswear called Hunter & Coggins that I patronise. Cheers.

Comments are closed.