Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Saturday, March 4, 2023

Why People Love Preppy Clothes. Why People Hate Preppy Clothes.

There is a group of clothes that I find perfect.  These include pure cotton khakis and baggy oxford shirts in a handful of colors, Scottish Fair Isles, British rain coats, tweed coats, D-ring motif belts, Maine made bluchers and boat shoes, toggle coats, tartan cashmere scarves made in Scotland and Aran sweaters made in Ireland.

These clothes blend into the New England coast.  They are ideal for getting in and out of boats, for students throwing on as they run across the quad with wet hair on the way to class, for casual business meetings that turn into hikes across Cambridge to find some obscure used bookstores. The pink and green match the beach roses along the New England coast, the blues feel like the ocean, and the Donegal sweater I am wearing right now has the rugged complexion of the rocky Maine coast.   

These clothes also fit my highest compliment, which is 'class-feral'.  They are the Herreshoff yachts or Sarouk rugs of clothes; they wear well.  They also, rather than highlight the wearer, improve the scene.  

Many would describe these as 'preppy' clothes.  I think of them slightly differently, as "the thing before preppy."  My parents wore such clothes as early as the '50s and '60s.  I “never didn't” have these clothes.  (For context, I grew up around New Haven, where my family has roots that go back to its founding in the 1630s.  One of my great grandfathers, Deacon Samuel Heminway,  paid the first Yale tuition in 1702, and another, John Brockett, laid out the Nine Squares of New Haven in 1638.) But we never referred to them as preppy.

And so it is of no surprise to me that people love these clothes.  They are timeless, tough, and comfortable. They have dash, not flash or trash.   They are especially perfect today, as suits and ties seem only to be worn by people who have to, and Silicon Valley has lost a bit of its luster.  One reason for starting my blog 13 years ago was to introduce new people to the pleasures and satisfactions of these classic clothes, which has only grown over time  

People sometimes confuse these clothes with conformity, but to me they are the exact opposite.  Because they are perfect, they take any need to think about clothes off the table and allow one to focus their creativity and innovation where it is needed.    

What has been more surprising is this pattern where people move away from preppy clothes.  I have seen this repeat itself many times in my lifetime, and it has started to get predictable. Once preppy clothes become a bit popular, forces rise to make preppy clothes first more appealing to greater numbers for the wrong reasons, and then the trend dies out. 

Here are some of those forces.

1.  Some people and companies want to turn preppy clothes into fashion.  They make them impractical, trendy, tight, and inevitably of poorer construction.  For example, some ambitious designer decides that because a Scottish made Black Watch scarf is preppy, then a made-in-China Black Watch mini skirt is also preppy.  There is the obligatory fashion article, where the writer is amazed that preppy clothes are being used for runway inspiration.  Customers buy one or two such items with high hopes and excitement, and they fall apart or fashion changes, and they move on. 

2.  There are people who adopt preppy clothes for social subterfuge.  Some want to look rich on a budget.  Some people believe they can get away with being bad if they dress well.   Others want the je ne sais quoi of actually having gone to an Ivy League school, or having grown up differently.  They want to impress their friends, or differentiate themselves from their siblings.  As a result of enough people attempting this, however, a shared belief emerges in a culture that people who wear preppy clothes are overcompensating.  The ruse does not work for long.

3.  Preppy clothes are often knocked off.  L.L. Bean famously imported a Norwegian Birdseye sweater, which became thought of as a preppy staple.  But after it gained a strong following, Beans fired their Norwegian suppliers and outsourced the sweater to China.  Soon after, demand dropped and Beans stopped offering it at all.   (It has since been reinstated, made in Norway, but 100% wool, minus the 20% rayon.)  A necessary part of preppy clothes is superior construction and attention to detail. Made locally is more expensive.  So cheaper clothes increase the popularity in the short term but hurts it soon after. 

4. Outsiders love writing about preppy clothes. But they always mix in their own cultures.  The goal is more appropriation of preppy clothes and culture than elucidation.  They get some facts right but virtually all analysis wrong. And they all cite each other.  I have yet to find any popular book, blog, or article that gets the culture right (even if some are still very funny).  Instead, we are reminded that fan fiction and trolling are two sides of the same coin.

So as soon as preppy is rediscovered, these forces soon enough take over.  People take classic clothes for granted, and so they lose them. To many, preppy becomes associated with trendy, poor quality, manipulative, or derivative, soulless, and shticky. 

For me, the cessation of public interest is a bit of a relief, but it can hurt good vendors and make staples harder to find.  

But soon enough, as in so many areas, the pure, unadulterated tone is then rediscovered through old photographs or resurrected examples. And the cycle begins anew.

39 comments:

  1. This is beautifully written and well said. The only redemptive part of "preppy clothes" being trendy is that the trend always passes, like an insufferably hot and humid August heatwave. The heatwave always breaks, and so does the "preppy" trend.

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  2. This style of dressing never goes out of style. Classic is timeless.

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  3. There are some things that were figured out long ago: planting in rows, two story symmetrical homes with a living room on one side of the stairs and a living room and dining room on the other, and clothing cut comfortably, offered in colors that pair well, and made of comfortable and natural fibers that wear well, thus offering good value. It is, indeed, the thing before preppy. In my experience preppy was when we kept the cut and natural fibers but veered into the realm of the garish. Some of the garish was good enough to keep, like pink and green, madras, and critter pants but all for a break, not as daily dress. Some things are lost or becoming lost in time like tennis whites, Sperry kudus made in the USA, and four speed stick shifts. I hold out hope for their return.

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  4. One of the great offenders is LL Bean. I can cite a list of great articles no longer offered or "modernized"; to cite my favorites: all cotton oxford shirts with decent length collars, country flannel trousers, wide wale country corduroy trousers, made in Scotland Shetland pullover sweaters , made in Maine hand sewn loafers, the list can go on.

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    1. Scotch plaid flannel shirts with collars that last longer than one season.

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    2. Calling Scottish tartan "Scotch plaid" is offensive to real Scots who believe that Scotch should only be used to describe whisky.

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    3. @Fred Johnson. Other great offenders include Ralph Lauren (the biggest fake of them all IMHO) and Gant. Gant's decline has accelerated recently under its current Swiss owner. There is no way that those rip-off brands can justify their price hikes of around 40% in two years.

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    4. Early on my Scots father in-law explained that Scotch was preferably single malt.

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    5. Your father-in-law was correct. There are several expensive whisky brands that should avoided at all costs, notably Johnnie Walker and Chivas Regal.

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  5. Kudos on pt. 4 - well stated.

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  6. LL Bean is horrid, whatever dye they use in their clothes turns yellow

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  7. I really enjoyed reading this. I especially enjoyed: "before 'preppy'" and "well-made". I'm glad we can count on Muffy to post about the 'classic' clothes that she finds that are well-made, Jack Donelly, Mercer & So. etc. I truly miss the days of browsing catalogs like Orvis, L.L. Bean, J-Press, Brooks Brothers, etc, placing an order and receiving *quality* clothing; those days are long gone. Orvis *had* great classic khakis and shorts, baggy, durable, and comfortable. I miss the old Brooks Brother button downs---ugh, I could go on for DAYS about how quality is a thing of the past. I just want classic, well-made clothes. As for preppy trends coming and going, I really don't care.

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  8. It is disheartening that the younger generations, familiar with older things in our closets, accept at face value the fallacious notion that certain labels stand for quality. Among the more notable ones, in addition to L.L.Bean, are Brooks Brothers, Abercrombie & Fitch, Eddie Bauer, Pendleton, G.H.Bass, and even (gasp!), for a growing number of items, J.Press.

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  9. Good point on #4- cultural appropriation is unappealing at best and offensive at worst. The only way to wear the clothes is with the ease and casual elegance that very few people have. I’m not one of those people but I have admiration and respect for those that do.

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  10. Agree with much of what's written, except --- I lived "preppy" in the 1960s (and continue to dress and seem preppy still). We knew then we were preppy and our clothes were preppy. We were called preppy. One popular local shop, in particular, opened in 1961 and carried these classic preppy clothes for men and women for decades. My mother clearly brought "ivy" influences from her university days to the ways she dressed us for grade school in the 1950s --- but, for certain, "preppy" had its classic look, quality, and "name" in the 1960s. Maybe even at the end of the 1950s? I do agree preppy clothes are not inexpensive but real quality and classic styles do last --- like a blue OCBD, half dozen sweaters, and a wallet and purse I still have from the shop mentioned.

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    1. Yes, as far back as I can remember -- this would be the late 1960s -- my uncle used to call my father "the old preppy." So the term certainly was in use then.

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    2. I've always known it referred to as "preppy" style and I'm old.

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  11. The first documented member of my maternal grandmother's family came to the area which is known today as North Carolina in the early 1600's. Many English settlers also migrated south from Virginia into the area of North Carolina to establish colonies. North Carolina became the colony of Carolina, settled by the English by around 1663 and chartered by King Charles II. Over generations, the Scottish/Irish clan Braly (now regarded as Irish) migrated across the Americas, settling across the Plains and others helping to establish the new state of California.

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    1. Quite interesting. I'm fascinated by the paths that Europeans took through this land over the centuries. My own ancestry, like that of many, traces through John Alden, but my limb of the tree found itself in the Great Plains. So I've no old New England or colonial cultural anchor to tie me to preppy or "class-feral" style, but my parents always had great clothes -- more cosmopolitan than preppy, with a similar appreciation for timeless durability.

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  12. One of your best. Certainly one of my favorites. Insightful, researched, and thoughtfully stated. Well done. I agree with you about the I was raised in by "preppy" parents in a traditional part of Virginia, and I agree entirely that it's difficult to articulate the essence of the culture. "Fast fashion" has taken quite a toll, and then there are the many affiliations with the excessive, vulgar opulence of the very wealthy. I'm at peace with the steady decline of popularity, since I'm convinced that it always been a bit of an insider's game. If a small % of the population flavor the brands and styling you reference, this -- well, it makes sense.

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  13. I totally understand and appreciate cultural appropriation. That said, I hope those of us who grew up on made in America, natural fiber, extremely comfortable clothing will gladly and willingly embrace all manner of us wearing it. It looks good on everyone. It feels good on everyone. It is kind to our planet. Plus, if we all wore it, prices would surely come down!

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  14. I think a lot of the trad apparel Facebook groups - definitely not this one - are partly to blame. They have attracted a lot of people who post all sorts of outfits , many of them foppish ( think movie version of Doctor Doolittle, with Rex Harrison) instead of cool - and ask " Is this Ivy"? Or declaim " This IS Ivy". And because most of the folks asking or saying this did not grow up with " the environment" , their approach is studied and often slavish, glom on to a world that barely exists anymore North of the Mason-Dixon line. Or never existed at all. They do not understand that the Northeast " elite" schools are definitely grade point average elite these days but usually no longer socially elite save some tiny pockets of genuinely traditional " sets" on some of these campuses. Most of the latter , " socially elite versus grade point elite is more readily found at the Southern schools nowadays.

    So what retail industry buying department people wind up with, in addition to cost pressures, is a demand based on an aesthetic amalgam . And it's a damned mess. People want (hopelessly parvenu) Ralph Lauren, which has an " expensive" reputation welded onto Ben Silver ( if not to the manor born then at least they do a damned good job copying it), with which they weren't familiar until last month, but that often doesn't work plus these zealous but misguided newbies often don't want that high of a price point!

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    1. I think it's one thing to write about the origins and unique regional culture involved in preppy dress, along with the broader market forces that co-opt said style, as Muffy has done, and altogether another to belittle the efforts of those not in the culture who are exploring what preppy means to them. Why shame people for slightly missing the mark when they're trying to find their sartorial way in the world? Bring on the experimentation, I say. Especially when it involves the good stuff. The young folks will find their own way with it as they grow into themselves.

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  15. Fashion has always taken inspiration or downright appropriated from many sources, so it’s not much of a surprise when it mines a classic American style for inspiration. There are entire brands and catalogs that promise preppy style for kids and adults, but sell items made with far less care and at a lower quality than what you discuss on SWNE. I appreciate this site’s focus on finding items that last, look good, and represent the best in class. (Although I also very much enjoy the pictures.) I think more and more people are recognizing the flaws in fast fashion: the waste, the temporality, the labor practices. Clothes can signal a sense of who you are and what you value, but only until one opens their mouth…then your character is revealed. If you value durability, form following function, fit, and quality, a label doesn’t persuade you and this site is a terrific resource.

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  16. Class and quality will out! Thanks once again!

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  17. I've been wearing khakis and boat shoes since I was a teenager. In addition, button down shirts and Navi blazers. For many, this often seems a bit artificial. But I always feel like I'm well dressed. Whether in the cinema, while shopping or actually on the boat. The boat shoes and khakis are as much a part of me as my 20-year-old Barbour waxed jacket and my Volvo station wagon.

    I also like that it's just timeless. I love my Ralph Lauren polos and Aran sweaters. When the polo shirts start to get holes after many years, I only wear them for gardening.

    For me, too, khakis and button-down shirts with blazers have largely replaced suits, although I still like wearing suits and I really feel very comfortable in them.

    I'm very happy that my wife shares my opinion about "our" preppy fashion. It never seems artificial to us.

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    1. “..as much a part of me as my 20-year-old Barbour”

      Wife is taking bets whether I or my Beaufort turns to dirt first

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  18. It just dawned on me that the more youthful cohort never encountered the stereotypical white kid stuck in a prep school, forced to wear coats and ties and get drunk on mouth wash, and well aware of things like collar roll and brands like Chipp. He has all but disappeared, and he has been gone for decades. The term "preppy" is still in use, but it has become obscured what it truly means in our larger culture. It means Abercrombie one day, Vineyard Vines next, Southern Tide following, and Filson next, mainly things we would not contemplate but a few we might.

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  19. Wonderful article and highlights why some love to hate authenticity. Or perhaps they simply don't understand it.

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  20. there was a time when one could get good cotton khakis and button down oxfords from LL Bean. No more, but it's still a good place to find a flannel or canvas shirt. I still wear one of those LL Bean fisherman sweaters from Norway...it's fine, but not really in the same league as similar sweaters from Dale or Devold.

    Preppy clothing surged in popularity when I was in high school in Connecticut - public school. It was more about fashion than embracing a lifestyle.

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  21. I've always worn the clothing listed here by Muffy, but never considered them to be "preppy." They were just "clothes." Everyone around me wore the same thing so much deep thought wasn't involved. Unknowingly, I guess I was really Class-Feral, and would just grab what's clean in the chest of drawers or closet, and leave. And most importantly for me, I wouldn't know what else to wear. What's the alternative? I consider this style of dress to be the best and most appropriate so it's pointless to keep searching.

    Trends in authentic Preppy Clothing? No such animal. An oxymoron with the emphasis on the "moron" part. They is what they is - everything else should go by a different specious name.

    Ancestry? I guess mine goes back to "Lucy" - 3.2 million-year-old humanoid/ape who, for some unknown reason, one day decided to climb
    down from her comfortable tree, and go strolling upright on the savannah. (One could argue that the human race has been on the downward slope
    since.) Anyway, scientists who discovered "Lucy" were most surprised and
    shocked to find out she seemed to have not made a late payment on her
    Mastercard and Visa Accounts in over two million years. Of course, all of this occurred somewhat "Before Preppy" appeared on the scene, and about three million years (give a day or two) before the Mayflower sailed from Plymouth.

    Switching gears, now if you want a classic 20% Rayon LL Bean Norwegian
    Sweater go to eBay - they have many in like new condition (it seems many people read the handbook, rushed out, bought the sweater, and then never wore it.) All to our advantage forty years later.

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  22. I don't know what is in or what is out. I know what I know and wear what I have worn since childhood. My parents wore wools, tweeds, plaids, khakis, etc. We had horses and boats. We weren't trying to be anything but ourselves. The horses didn't care. The bottom of the 42 ft Chris Craft needed to be scraped regardless of who made our khakis. The white split rail fence surrounding our property wasn't going to paint itself.

    What I am saying is, we are who we are. Fads, gimmicks, trends come and go. We're going to just keep being ourselves.

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  23. Before we were even teenagers our pockets were full of money we earned ourselves. We strolled York Street like we owned it. After patient Yalies took
    our seats at Yankee Doodle, we headed for the Co-Op. Barrie’s, Gentree, et al.
    “Ivy,” “Collegiate,” “Preppy,” call it what you will. Those were the clothes we bought by default.

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  24. Wonderfully fascinating essay. Grew up without concern for the term preppy, until that book was published decades ago—the one that garnered so much attention. Anyway, who calls other people names? Thought clothes fell into two important categories: useful or smart—happily both, if you have an eye for it—and to be worn according to need and occasion. Used to wear lots of lovely, comfy, all-cotton khakis, until they became hard to find, at which point, I leaned on skirts and unstructured natural-fiber pants to wear with hand-knitted sweaters or jersey tops and quilted jackets. Have forever worn moccasins (with cozy socks) or ballerinas, unless the weather is inclement. Never wore tennis shoes, except for playing tennis; avoided court shoes, but always keep a pair at the ready for when I can’t avoid wearing an afternoon dress—a consideration that’s on the trail of the dodo. Am not knowingly susceptible to trends, nor have I consciously purchased clothing for any reason occult or devious, beyond sartorial cunning. Then, again, I do have piercingly fond memories of what what was worn by the people I love who have died. Do I dress in homage? Actually ... Oh, I see ... Hmmm …

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  25. I live in Marin County, California. I was talking to my mechanic. He is seeing a boom in people buying used cars and putting money into them to make them good as new. They'll say things like: I just bought this- let me know when I've spent 12,000 dollars...There are are also way more fully restored classics around. I for one don't want a huge i-pad in the middle of my dashboard. I have a neighbor with a 1970 Mercedes 2 door convertible with a small v-8, and a handmade body. She's younger than me, but she says it's her last car. Try to find a 940 Volvo wagon for sale- they're still on the road, but not for sale.

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  26. This is the epitomizes where preppy is derived from. Forgive me, but I often equate preppy and this blog with uptight New Englanders who exude pretense and heir. Reading this entry has opened my eyes. You growing up with this before preppy was "preppy" makes all the difference. Thank you.

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  27. Reading this in Rancourts and Brooks Bros shorts.

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  28. I am an early 50's professional, tall, slim male, and while I like preppy clothes, and previously wore a lot of them, I have distanced myself a bit. I prefer a more tailored look in a chino (slim fit) and definitely prefer a slim-cut button down. I still buy high quality, but less preppy, for sure. Curious though, Muffy; I appreciate your style, but the more generous cuts do make it very classic. What is your formal go-to for dresses/shoes, or have you ever gone outside of preppy? I have three sisters, and I wouldn't describe any of them as preppy, but they all have impeccable style, dare I say, more metropolitian, avant garde. Do you every dip your toe in this genre? I would love to see you in something outside of preppy!

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