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The Modern Guide to The Thing Before Preppy

Thursday, September 1, 2022

"How a Younger Generation Learned to Love Old-Money Aesthetics" - Robb Report

It seems every few months there is a new article about preppy clothes and lifestyles.  What do these types of articles get right and what do they get wrong, looking at their facts, analysis, and feel?  

A current example, sent by a friend:


52 comments:

  1. These articles make it clear that people struggle mightily to think outside the postwar triangulation of education, jobs, and money. More specifically, that a person gets an education to work in a job that then pays them a sizable amount of money.

    People write whole articles like this trying to describe a life in which education, jobs, and money are separable, and they can't seem to see or describe how that freedom is built and practiced. They appear to be distracted by old cars and watches.

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    1. I see these things as a form of cargo cult. It mistakes tokens of achievement for actually achieving something. "If I buy the right things, and wear the right clothes, then an old-money lifestyle will become mine."

      If we put out wooden crates in the jungle clearing, the sky gods will fly over, see them as an airfield, and return to give us cargo....

      And we see something similar in cases where getting a house via a no-down payment mortgage (for example) is supposed to make a person middle class all by itself. But being able to afford a house (with a down payment, etc., etc.) comes from having the certain life habits: living within one's means, saving, having a long time horizon, and a willingness to defer gratification.

      To bestow tokens of success on people who lack the ability to earn them through their own efforts is both cruel and disastrous — for the person and our society.

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    2. Brilliant and insightful.

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    3. ^ I enjoyed this exchange and Kaaterskill's comment below as well.

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    4. Re: Anonymous, isn't the whole point of "old money" that it isn't earned through one's own efforts, but rather that of an ancestor?

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    5. *those of. Darn it!

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    6. @Nevada: I guess an "old money lifestyle" is yours to display only if it comes from your own ancestors. The point is, it can't be bought, and any bestowal must come from your personal line of descent.

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  2. They're also very misguided in their fixation on the Ivy League. Most of the Ivies (Brown perhaps excepted) have made conscious decisions to become global institutions, and their cultures now reflect that multicultural mashup. A walk across Yale's campus looks very different than the SWNE aesthetic.

    If institutions with a critical mass of students who grew up wearing button downs, learned to drive in a Volvo 240, and spent summers sailing still exist, it's at places like Bowdoin, Colby, Bates, Middlebury, or even Colgate. Good schools, but much more culturally local than even Amherst or Williams.

    Harvard, Yale, and Princeton, not so much.

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    1. small point, but Bowdoin has become very diverse and exceedingly competitive for admissions, in the same tier (slightly more competitive for admissions, actually) than Williams and Amherst.

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    2. @andrew That's too bad, not the diversity at Bowdoin, the competition. US News and their ilk are ruining the character of American higher ed.

      Hopefully the hyper-competitive meritocracy hasn't come for Bates and Colby, too. That way lies a blah sameness were you could wake up at Hamilton, or Kenyon, or Carleton and not immediately be able to tell the difference.

      Addressing the Clouds: Leave our little schools alone to be their own special places.

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    3. If you woke up at Kenyon you'lld know where you were.

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    4. Kenyon has the most beautiful campus of any college I've seen. It's academically excellent too.

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  3. Millennials and Zoomers want to feel a sense of easy elegance, and frankly, also an uncomplicated life, if only for an evening out. This usually translates more to theatre than to an actual lifestyle with intrinsic habits, but it's not hard to understand why people would lust for the privileges that the most privileged Boomers have had.

    Although the performances leave room for refinement, there aren't many examples in daily life that people can look to for inspiration of the "real thing"...including most of the children of "preppy" Boomers.

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  4. Manners and politeness are immutable. They are the bedrock. Everything else waxes and wanes. It’s as simple as that.

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    1. Your comment is wonderful and most insightful. Manners and politeness are the most important things to teach our children.

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    2. I was always taught that "manners maketh the man" and I still believe it

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  5. Although I went to a public high school--in Princeton, no less, but not that Princeton--I have known a couple who went to a prep school. I think they would have found that article to be ridiculous. It seems to have been written from a New York, meaning Manhattan, perspective. One doesn't have to be a New Englander or New Yorker to be a preppie. You just have to have gone to a prep school. I'm not sure if you have to graduate, though, since The Official Preppie Handbook mentions getting kicked out, and one that I know, a family member in fact, did get kicked out. But he went on to have a career in journalism and has had a few non-fiction books published. Another I knew had a career in the foreign service, mainly in South America. Neither went to an Ivy League school.

    My own father, by the way, never attended high school.

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    1. Interesting stories. Was there not a high school near to where your dad lived? Or was he interested in other things ?

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    2. My father grew up on a farm in southwestern Virginia, one of thirteen children that lived. He was born in 1914, drafted into the army at age 28, was a POW for a year in Germany. I was stationed near the location of the POW camp for almost two years when I was in the army. He drove a truck for most of his life, but he also worked some in a mine, "worked cattle" (that is, a cowboy), and of course, worked on the farm. He only went through the 6th grade and sometimes struggled to read. I, on the other hand, graduated university and I live in a nice suburban neighborhood outside of Washington, D.C. I also married someone with something of a pedigree, although I was totally unaware of it before we got married. Even after 40 years, I don't have it all straight.

      I mention these things because I imagine some people have no idea how people on the other side of the tracks or the other side of town have lived their lives. Maybe not even the people next door.

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    3. Beautifully said ! That is what life is about. We are all one big community wether we like it or not.

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    4. I thought my comment was a little clumsy and probably self-serving. But here's another, more interesting story.

      Where I was born and grew up (where neither my mother nor father were born), I used to joke that kids grow up and build a house directly behind their parent's house, although I actually only knew four that did that. But then I move to the big city, or more correctly, the big suburb, and wind up marrying a young lady who also grew up directly behind her grandparent's house. The house is still in the family and has been since before the war (meaning the Civil War). She was also born in the same hospital her father was born in and we were married almost right across the street, just a few blocks up the street from the White House. Her great-grandparents lived on Capitol Hill, where the Library of Congress is now and that's where her great-grandfather worked.

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    5. Blue Train - thank you and your father for your service!

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  6. I would hope that people would be returning to this aesthetic not to emulate a look or recapture an era but to embrace good sense, comfort, and a sense of dutiful stewardship that uses things up, wears things out, repairs things, and makes do with what they have. All the while they find their pleasure in settings of greater social intimacy than in loud clubs. I think savings my sweats for workouts, slipping on my loafers, and joining a few friends for two martinis sounds wonderful.

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  7. So what? It's about an image, not the way of life that created the image in the first place, and it's temporary. When I was in college in the late '80s, "old-money aesthetics" were mainstream and provided welcome relief from the excesses of the '70s, but then fashions changed again and everyone wanted to be "grunge" or "urban" or whatever, and a lot of people who had been reading Allan Bloom and listening to Pachelbel's Canon and wearing Brooks Brothers suits stopped worrying about the closing of the American mind and took up Nirvana and Chicago Bulls jackets. Most of the people in that article will very soon be wanting something else.

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    1. You are absolutely right. A telltale sign is the omnipresence of "designers" in the article. Designers can confirm what's happening today, but you can be damn sure they'll be onto the next thing tomorrow.

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  8. I think the article represents one slice of a younger generation, but I doubt it's a majority. We have two grown children living in New York City, Kips Bay and East Village, and they're neither obsessed with their social media presence nor striving for some new approximation of an old money lifestyle. They are much more focused on working hard and experiencing life than accumulating material things....even very well-compensated people can only pack so much stuff into a New York apartment.

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  9. These articles make Trendy Preppy sound much more mainstream than the reality. I've been seeing articles that tout 'neo-prep' for over three years and have yet to see anyone wearing neo-prep clothing outside of social media or an article touting neo-prep. I agree with the above comments, anyone following this trend is going to be dressing and living differently once something else catches their eye.

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  10. My humble opinion is that our millennials and Z-ers are God-awfully lost. --Holly in PA

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    1. Mine aren't. My millennial son and daughter-in-law are smart, contributing, active, involved members of society, as are their friends. Perhaps you need to seek out some different younger peeps?

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    2. I agree with Patsy. A lot of the young people I know are smart, hard-working, and want to change the world for the better.

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    3. I tend to agree with both Anonymous, 4:51pm and Patsy, to some extent. I believe that the number of status / consumption obsessed young people is less than you would believe by viewing social media, because these people tend to be drawn to the apps at a higher rate. However, in my state and my social circles, there are certain groups of individuals who emphasize "aesthetics" nearly as much as the experience itself. I think immediately of restaurants and bars with ostentatious presentation, but poor quality food, decent service, and strong brands. Certain clothing companies reflecting the same qualities tend to be popular as well. Even those of us not posting / viewing social media at high rates and with the same emotional dependance tend to be influenced by this line of thinking.

      If those individuals who care more about aesthetics than quality purchase cheap goods at high rates, other, traditional manufacturers, will simply follow the money/trend or be "left behind." This it more difficult for those who are selective in their purchases to even find quality goods. It is the same with restaurants. In our town, a handful of reasonably priced bars/restaurants have closed, replaced by "trendy" modern locations with prices 1.5-2x the prior price. There are multiple factors at play (inflation, rising average incomes), but shifting preferences by those with a high appetite for consumption tends to shape the experience of everyone.

      I agree with Vecchio Vespa and Casabian. These individuals and businesses confuse aesthetics with the values that they have come to represent. Individuals drawn to lives of purpose and connection, yearn for a positive impact on the world, self development, a social life, etc. Whether individuals represented by words like "preppy" and "Ivy" ever lived lives matching these ideals can be debated. The esteem placed on certain individuals both in literature, film, the news, and marketing campaigns, created the tie between these values and these goods. The hollow feeling of purchasing clothes, cars, houses, and not experiencing a lifestyle change should drive individuals towards introspection, but often, it seems, it drives them towards further consumption.

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  11. I wouldn't mind seeing more young people dressing and acting well...even for a little while and for the wrong reason. Maybe some of it will stick. Fake it 'til you make it.

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    1. What we are on the inside is so much more important than how we look on the outside. The outside is irrelevant in comparison. So, faking it until you make it applies to both.

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  12. While I have no interest in "Trendy Preppy" I do like the idea of more places featuring the Great American Songbook. What a relief that would be.

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  13. “Great American Songbook” like Bob Dylan, Woodie, Paul Simon, Chuck Berry, Brian Wilson, Robert Hunter and Jerry Garcia ?

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  14. It's nice that the young folks are getting dressed up to go to the Carlyle and so forth, and I'll gladly take it. But it's a TikTok thing, which means this will be a pleasant but short-lived trend among the surprisingly chameleonic Zoomer generation. And the fixation on certain extremely high-end brands, understated though those brands may be, means this is more of a status/competition thing than a genuine lifestyle thing. But they're young yet: There's time to get real.

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  15. Its time to issue all the millennials and Z-ers copies of The Official Preppy Handbook for guidance.

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  16. High IQ comments throughout this interesting Post.

    Today, I think the Old-Money Aesthetic isn't about money, but about a psychological yearning for freedom, and the throwing off of societal chains.
    The article's point about all this being a reaction and rejection of Woke Culture is well taken.

    Woke, of course, is similar to Puritanism - emphasizing uniformity and the restriction of personal freedom. Rules, rules, and more rules. Rules on how and what to think, rules on what to say and not say, rules on who to associate
    with, rules to avoid stepping on hyper-sensitive toes, rules to save you from the Thought-Police, rules to prevent you from being cancelled, basically rules to regulate every aspect of your life.

    Yes, the essence of Woke dogma is a marriage between Franco's Spain, and North Korea - no wonder the kids want to escape and are embracing what they perceive to be Old-Money Aesthetics. "Please, just let us live and enjoy our own lives!" is what they are saying through this neo-hedonism.

    And more power to them.

    ---Robert Reichardt

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    1. And I present that same idea to you. Live and let live. That goes in both directions.

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    2. I think it's generally members of the older generations who feel so put upon by what they're pejoratively calling "woke-ness." The Gen-Z'ers are, on the whole, the most open-minded and accepting generation yet. They're not the ones concerned with whatever "woke" has come to mean for us "olds." To refer to the encouragement of a more kaleidoscopic social world as "puritanical" is to misunderstand the young folks entirely.

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    3. And then there's this. https://www.youtube.com/watch?v=9IEFD_JVYd0

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    4. I don't really know what twenty somethings mean culturally and politically with their aesthetic choices, but there's a strange desire among fashion writers to try and divorce clothing from politics.

      The prep of the 80s was most definitely a reaction to and rejection of the excesses of the 70s, which is uncomfortable if you're a leftie (raises hand) who likes tailored clothes and traditional looks (raises other hand).

      On the other hand, we've gotten so casual that putting on a tie is pretty subversive.

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  17. I echo Nevada's sentiments entirely. Instead of snivelling and bellyaching at the younger generation and the presumed 'woke-ness', I think they're to be applauded for at least ascribing to a more appealing aesthetic, so I choose to keep a positive view. And as someone who in the early 90's, used to enjoy listening to Bobby Short at the Café Carlyle, and enjoy a Bellini at Harry Cipriani every Saturday evening after shopping at Bergdorf Goodman, I actually enjoyed reading the article.

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  18. According to Merriam-Webster, woke means : aware of and actively attentive to important facts and issues (especially issues of racial and social justice). It seems to me that this is a positive thing and always has been. I find the twenty-somethings and thirty-somethings I know seem to have it folded into many facets of their lives. It is in my view an essential corollary to freedom.

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  19. The vacuous Robb Report article was indeed a painful read. Civilized behavior based upon work ethic, education, knowledge and appreciation of culture for the purpose of making a contribution to society is not found in a book about emulating Preppy lifestyle.

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  20. Fascination with class, status and wealth is unhealthy. It is unfortunate that some individuals systematically choose this focus. The person they become is often misguided and/or malfunctioning. One such individual once stated to me: "I do not know how to be successful." Telling.

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    1. This is also true. Whilst I enjoyed the trappings of status and wealth in my 20s and 30s, I am no longer impressed by them and dress the way I like and that is comfortable to me. So often that means a New England aesthetic, but not slavishly, I might add, and at my age of 60, I am confident enough in my own identity to not be bothered a whit by what others think.

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    2. Agreed! I am right behind you in age and feel the same. While invariably what I wear would be identified as prep, I wear what I wear because it works for me and my purposes. The hoot of it is the vast majority of my clothes that receive notice or compliments are from thrift stores or are decades old. If some item is a little weary looking I just explain we live in genteel poverty. Cheers!

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  21. Much as I love the New England/Trad/Ivy/Old Money look, I feel like a poseur if I try to emulate it in my wardrobe. I love navy but it's hard to find the kinds of things I adore in navy, so, I wear a lot of black. It is easier for me: more economical, allows me to be less obtrusive where I live, looks neater and cleaner. But I adore the traditional/heritage look.

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