Photo by Salt Water New England

Thursday, October 7, 2021

What Are Things That People Think Are Preppy but Are Not?

 

A reader question:

Greetings Muffy,

I have a question for the community.  

The number of people who experienced the preppy life before it was named and turned into a mass market was always small, and getting smaller.  However I think a fair amount of them are on your site.  My question is simple.  For those people who were annoyed by how much TOPH got wrong, and obviously by the derivative examples since on social media, what are things that people today think are preppy but are not?  

What are things that were never really preppy (such as Jeep Waggoneers, too cheaply made), what are things that are no longer preppy (such as penny loafers, too ugly), and what are tells (terms such as "OCBD", "Trad", "popped collar") that make you realize instantly the person is not of the world.  

I suspect some people will say that talking about preppy is not preppy, which is absurd.  If we don't talk about it, the only people that will talk about are the people who don't understand it, who are exactly the people who say that. 

Thank you.

 

58 comments:

  1. My late mother and uncle were and are the real thing. Prep schools and, in the case of my uncle, ivy league for undergrad and Ph.D,. In all of the years of listening to their conversation about all kinds of people, places, ideas, and things, I cannot recall ever hearing them (or my late grandparents) talk about clothing, attire, views, or lifestyle any more specifically than using terms like "classic," "appropriate," or "We don't do that dear" (with stress on the the we). They simply liked what they liked, avoided what they did not, and were generally kind even to people outside their circle. A shirt was simply a shirt.

    Kind Regards,

    Heinz-Ulrich

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    1. Wonderfully said. My mother's family were the same way. My beloved grandpa was always elegant and well-groomed (so much so that he was a sartorial inspiration for me, even now) but he was kind and never condescending, never placed himself above others. This is also why I never use the word "prep" to distinguish myself from others but in a very tongue-in-cheek joke-y way.

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    2. That commentary was wonderful to read. You nailed it.

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    3. I'm from a Princeton family going back for generations, but I can't remember anyone in our family ever talking about being or not being preppy or wearing or not wearing preppy styles. The only thing I remember is that my mother said we should wear really good quality clothes and take care of them because we wore them as long as we could. I rebelled in the late 60s (when it came to fashion), but later returned to that understated, classic, uniform-like style.

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  2. I’m curious what this reader thinks actually is preppy—I don’t agree about Wagoneers or penny loafers, but maybe that means I’m out of the club, despite attending prep schools etc.?

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    1. Same here! Oh well. Will let all the Jeep driving, Alden loafer clad exiles at the Trinity-Hamilton tailgate know their fate as well. Apostates all.

      That said, I agree regarding the terms “trad” and “OCBD.” Speaking of which, have I missed a review of the Brooks return to the original oxford? (Sort of a return - they’re in S, M, L, XL)


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    2. Penny loafer girl here. I have always worn them and will continue to wear them. I don't care what others think, nor do I find them to be "ugly".

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    3. I still love them too. I just need to find a new brand that fits well since Bass has totally trashed their Weejuns line by "upgrading it". (Insert huge eyeroll here...)

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  3. My thoughts on this are endless. Buying new things each season instead of rewearing the classic pieces you have; saying "with a twist" unless you are ordering a martini; being rude to waitstaff and shop clerks; boasting; conspicuous labels/branding (i.e. Burberry plaid); "statement necklaces."

    I think that wearing simple, well-made clothes that are practical for the occasion, being polite and kind to all, and being understated are key virtues.

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  4. Things that have crept in behavior that are most certainly, and not exclusively, not preppy: Boastfulness. Rudeness. A sense of entitlement. Conspicuous consumption. Disregard of others.

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  5. I don't think of myself as "preppy," and I do enjoy my OCBDs and penny loafers, (which I would argue are considerably less ugly than most currently popular casual shoes). I also grew up riding in Jeep Wagoneers. So perhaps my personal disinterest in the term, "preppy," as a label does align with the reader's position. In the 80s, lots of prosperous folks living outside of New England and possessing neither ivy league cred nor Mayflower blood wore clothing like that, stuff right out ofthe Birnbach book (or the Tom Shadyac poster). They may or may not have thought of themselves as preppy. And without those two affectionate parodies to refer to, maybe the word itself wouldn't be so loaded and I'd be fine with thinking of myself that way.

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  6. I think for that moment in time the OPHB did a pretty spot on job, but each era has its hallmarks. With the jettisoning of dress codes, prep school tastes and public school tastes have largely merged. With the proliferation of financing options and the misfortunes of Detroit, tastes in cars have become quite different for many, and in the main preps and non-preps drive much the same vehicles. There remain some, a group distinct from preps, for whom "buy well but only once" remains a core value. For those from older generations, things like khakis, OCBDs, Shetlands, blazers, tweeds, and, yes, penny loafers remain fixed and constant, as do utilitarian cars and SUVs built to last. With our heightening awareness of our impact on the environment and the importance of a healthy economy I see more people returning to durable and serviceable things as well as a beginning renaissance for MiUSA goods. People who act entitled and superior, not just those who attend prep schools, are still obnoxious.

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  7. I am stunned that my shoes are “ugly”. My penny loafers are versatile, comfortable and more stylish than the sneakers that have become ubiquitous in my office.

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    1. Wholeheartedly agree. I have worn penny loafers that are so comfortable, yet decrepit, and not think twice about it. A little polish and a brush up and they are quite serviceable day in and day out.

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    2. As a 60 year-old male I don't know what I would wear for work other than loafers and wing-tips. I've had a devil of a time finding good looking, reasonably priced replacements. Can't really justify Alden's at this time. Did find some nice Allen Edmonds on sale today.

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    3. Try Shoemart's Alden Factory Seconds. I can find nothing about them that is less than Alden perfection and I save $200! I just wore CXL LHS from there. Bliss for my feet.

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    4. I strongly recommend Crockett & Jones's Boston penny loafers. I also have Shipton & Heneage's Wiltons which are made by C&J on the classic 72 last. Style and quality are never ugly.

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  8. "Preppy" should never be conflated with the [crass] term "classy" or "elegance".

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    1. I'm confused - how is classy or elegance considered crass (lacking sensitivity or intelligence)?

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    2. I think the poster meant the word ‘classy’ isn’t, well, classy. I’ve heard that said, too.

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  9. I'll remind folks that the "Handbook" was a parody, not a primer. Alas, I was a mere commoner at a large state university when it came out 41 years ago.

    Today, I live in a world that understands there are subtle but important differences among preppy, trad and ivy styles, but would never be so elitist as to judge others for choosing to wear one of them.

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    1. The Handbook was not a parody, it was (gentle) satire.

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    2. Whether satire or parody it nailed a moment in time.

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    3. It didn't quite nail it, but it came close.

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    4. I still have my copy that I got in the '80s and greatly enjoy re-reading it from time to time.

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    5. If any of you read the 1983 British OFFICIAL SLOANE RANGER HANDBOOK, you'll have noted some relatable parallels to OPHB. Cousins across the pond, indeed.

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    6. The Sloane Rangers have been extinct since the 1990s. The English upper classes now wear "designer" labels rather than Barbours and tweed. They have left London permanently for the country over the last 20 years. Chelsea, Belgravia, Knightsbridge and Mayfair have been taken over by mega-rich Russians, Arabs and Chinese.

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  10. A few years ago, in my 50s, was out raking leaves in Colorado while wearing a uni stripe OCBD, khakis, and Top Siders, same thing I wear every non work day. My neighbor walked out on his deck, chuckled, and asked why I was so dressed up.Was pretty clear by tone that he had noticed it before. I was somewhat insulted (by what was a put down) but at the same time complimented for reasons others here will understand.

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    1. He obviously " didn't know any better"!

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    2. Using a rake and not a leaf blower. Now THAT’s preppy

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  11. Polo shirts with big logos.

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  12. Preppy is everything and nothing. To an outisder like me these labels like preppy, Ivy or trad a mostly artificial terms used to describe phenomenons and thus attempt to push them in a rather narrow frame of reference to make them identifiable and descriminable. The things which are given these labels today were just what people used to wear, drive or did in their freetime in the time from the 50s to maybe the early 90s and as such also changed over time. This means that sneakers are just as preppy as hoodies or OCBDs and chinos. Things can never be preppy but people are.

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    1. Why do you read this blog? I read it to confirm that my values, clothing style and interests are still relevant. I like knowing that there are people who still believe that "trendy" is a perjorative. Sneakers are preppy when you play tennis. Hoodies are preppy if you are jogging in the rain.

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    2. No, hoodies are never preppy, and only appropriate when one is looting a Target store seeking "justice."

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    3. I'm wearing a light blue alpaca knitted sweater with a hood today! Should I loot the Target in Revere (on my way home) or the one in Salem (somewhat out of the way, but would be considered a preppier town)?

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    4. Patsy,

      That all depends on what you want to loot? I hear the Salem store has a better selection of big screen TVs in stock right now, and it's also more out of the way for the mob as well. Your choice.

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    5. I read it mostly for fun and the pictures.

      Why wouldn't these things be relevant? I just hope that your values are independent from clothing style.

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    6. I read this blog for the photos of Land-Rovers. Still hoping for a Rover sedan now and then. I don't watch TV.

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    7. Robert, or perhaps we should go watch the hoodie adorned looters of Wall Street instead of Target. The crowd is sizably bigger.

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    8. Sigh..... a light blue alpaca knitted sweater with a hood is NOT a hoodie. And Wall Street is not known for their hoodies, they're known for their vests.

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    9. Patsy, go to Danvers. You can hit Total Wine at the same time and go home with an awesome stash of craft brew!

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    10. Why would anyone care about being relevant? I would only care about wearing what I enjoy wearing. I couldn’t give a hoot about what anyone thinks is relevant or if I’m doing what is proper.

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  13. Ah, penny loafers. Just starting to get broken in when the toes are wrapped in white athletic tape.

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    1. Depends on the penny loafers. That was the case with Weejuns. My last pair of Aldens gave me 32 years being worn at least 4 times a week.

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    2. shell cordovan Alden loafers might be my favorite shoe, and they will probably outlast me (resoled every so often).

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  14. The obsessive use of the word "preppy" in 2021.

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  15. I'm concerned that the reader was annoyed by The Original Preppy Handbook in 1980 and is still worried about it in 2021. Preppy or no?

    And, you'll pry my penny loafers off my cold dead feet.

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  16. This gets to the philosophical question. Is it "what is preppy?" or "WHO is preppy"?

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    1. Nope, nothing philosophical here - you is or you isn't.

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  17. In the last decade or so, I've noticed a blatant overuse of monograms (especially among some Southern ladies who seem eager to put them on cars, thermos bottles, laptops, etc.) I suspect this is deemed pseudo-preppily "klassy."

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  18. I recently read that "preppy" style is coming back into fashion. That's preferable to the indie/hip hop/trashy look that's been popular. Oh, and ripped jeans....does someone aspire to look cheap and homeless?

    I love my penny loafers. Recently I found a pair of Quoddy bluchers in a thrift store for $15! Just my size, newer soles and laces on them.

    Lately I've been trying barefoot/minimalist shoes and really loving them. (Wider toe box, zero heel drop, very flexible). But the choice for women's shoes that aren't too casual is limited. And being wider, they look a bit like clown shoes, but are oh so comfortable. Loafers and bluchers can dress up any outfit, but when I really want comfort I'll wear my Xero running shoes.

    Almost all of my clothes are preppy/traditional and aren't replaced unless they wear out. Always in style.

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  19. In college (even in the countercultural '70s) I came to realize that on occasion girls were attracted to guys in well-tailored three piece suits, wing tips, OCBDs and rep ties. Once time a (beautiful, sexy girl I had an intuition about and wanted to meet) stopped by a friend's room where we were studying. She seemed to fall into a wide-eyed bit of a swoon over the way I was dressed. She had a bad ankle... or said she did. I offered to pick her up to carry her to her room, which she accepted and I did. It was the beginning of a year-long relationship.

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  20. My penny loafers contained dimes so I could call home if necessary. They were and still are the best shoes.

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