WWD On The Rebranding Of Preppy, With Quotes By And From Ivy Style

As hinted in our last post, we continue with an examination of the rising revival of neo-prep. It comes to us from the trade publication Women’s Wear Daily, which absorbed the menswear publication DNR several years ago. Recently I spent a fun but exhausting near hour speaking with a reporter from WWD, and last Monday the story came out. It’s entitled “The Rebranding Of Preppy: As the cultural climate shifts, brands are attempting to reposition preppy to appeal to more customers or not use the word at all.”

The story is pegged on the Rowing Blazers brand, recently founded by Jack Carlson (disclaimer: friend and advertiser). Jack is certainly doing more than his fair share of giving prep-inspired classics fashion appeal, garnering a ton of press (of which this is just the latest), forging all sorts of collaborations, and hosting regular shindigs at his summer pop-up shop here in New York.

The story is locked behind a WWD paywall, and the reporter sent me a PDF, requesting that I only share snippets. Fortunately someone has pasted and posted the story, which lets us off the hook.

The story opens with the same orthodox-vs-fashion opposition that emerged in the comments section of our last post, which featured Sperry’s “Prep For All” campaign from earlier this year.

One sunny afternoon a gentleman in his late 40s walked into ‘ New York pop-up on Rivington Street. He asked the brand’s founder, Jack Carlson, to join him next door for ice cream at Morgenstern’s, where he proceeded to offer Carlson unsolicited advice about his line. The man was a Princeton graduate, preppy and pleased with the brightly colored rowing blazers and rugby shirts Carlson designed, but didn’t like the T-shirts he created with .

“He said something like, ‘They have no place in the brand,’” recalled Carlson, who is 31. “I was polite, but in my mind I was thinking it’s my brand and if I think it’s cool, then it makes sense. There are people who don’t quite get it, but you never hear any of these comments from younger people.”

I spent a lot of time with the reporter talking about my assessment of words and their meanings, and how they change over time. “Preppy” had become so watered down over the decades, I said, that it’s no surprise that the word “trad” caught on in the digital era. The Sperry video seems to illustrate this very point: prep diluted to a point where one wonders why the term is even invoked at all. Sperry is quoted in the article with the following:

“We aren’t denying that we are preppy, but we wanted to open the boundaries and let people know it’s OK to interpret preppy in your own individual way,” said Kate Minner, Sperry’s chief marketing office. “The customer doesn’t want to be told what to do.”

J. Press also snags a mention in the story, voicing its intention to get back to basics rather than fashion-dilute the style even further:

The company recently brought on Robert Squillaro, who previously worked at , to streamline the brand as senior vice president and chief merchandising officer. According to Squillaro, the J. Press customer is underserved and looking for classic, American sportswear and tailored pieces that most companies have stopped making — with the exception of The Andover Shop located in Harvard Square in Boston, which is seeking new ownership, or O’Connell’s Clothing in Buffalo, N.Y.

Instead of trying to chase a wider audience — J. Press is privately held by Onward Kashiyama USA and operates three stores — the brand is getting back to the basics with a print catalogue and its flagship at the Yale Club in New York City, which Squillaro said has increased business significantly. But the company remains keen to attract a younger consumer, which it plans to do with a more fashion-forward line to make its debut this fall with slimmer fits that will accompany its classic heritage assortment. The lines will be distinguished by tag colors. Squillaro also hinted at a collaboration with a designer to be released later in the year.

My long chat yielded all of one quote, which is completely understandable as the story’s focus is clearly on other matters (remember, I do this for a living, too). And our notoriously curmudgeonly commentariat grabs a dubious passage as well:

But preppy purists — those of them who are left and who live in the comments section of sites like Ivy Style — aren’t ond of the interpretations. Under a post on Ivy Style about the opening of Rowing Blazer’s temporary Grand Street store, one commenter, who identified himself as Christopher Hosford, stated: “Fashion aside, I am inherently prejudiced against clothing that purports to identify a wearer as a prep or university varsity athlete, when indeed he was no such a thing.…The glowering fellow with the shades and regatta patch — he probably hadn’t seen a body of water bigger than a Crown Heights mud puddle nor rowed across one — is a particularly risible example.”

“I think the purists feel left out,” said the founder of Ivy Style, Christian Chensvold, when asked about the current state of preppy apparel. “For my readers who have grown up on a brand like Brooks Brothers, they believe what’s happened to it is an utter travesty and a complete dismantling of the greatest men’s wear institution in our history.”

In the digital age, it would seem fashion cycles have gotten shorter and faster. Just five years ago we wondered about the uncertain future of neo-prep. We may be getting our answer. — CC

31 Comments on "WWD On The Rebranding Of Preppy, With Quotes By And From Ivy Style"

  1. Great quote, CC.

    As for this: “…fashion-forward line to make its debut this fall with slimmer fits that will accompany its classic heritage assortment.”

    How’s this “getting back to basics”? How do we square this prediction with Millennial Fogey’s hopeful outlook? “Fashion forward”? Ugh.

    If only J. Press would focus on great cloth, top drawer tailoring, and classic styling.

  2. I wonder who’s making the blazers for Carlson. Greenfield?

  3. ” Deck chairs on the Titanic”, etc. Last night I attended a musical
    at the prestigious regional theater in Palo Alto. Preppy? a mile from the
    Stanford campus, British?, Neapolitan?, No. Slobification. Many age
    groups represented with a preponderance of males of an age who
    dressed trad, more or less, for work, even in tech, a few decades ago.
    The utter lack of style, fit, even neatness, was appalling. I realize
    that this is Silicon Valley, a very high net worth area never known for
    style.. But 50 year olds who drive $100k cars, own $ 5M houses
    choose to dress in a way that combines homeless shelter and clueless nerd.
    There has been a cultural shift. I am afraid that many of the efforts of the
    traditional menswear industry will be futile.

  4. These guys spend their whole lives pretending to be a character in a Wes Anderson film. Interviews of Castleberry showing us all how quirky he is by hitting golf balls off a Manhattan rooftop while dressed up like Chas Tenenbaum in a polo coat are so obvious and try-hard. Equal effort is always put into creating the same cliché environment of flee market nick-naks, as is the ‘preppy-with-a-twist’ clothing itself. Creative types should naturally follow passion over monetary value but one wonders if the effort is worth the income generated; especially considering the cost of living in NYC these days (Brooklyn included).

  5. Can’t help but think that so many younger critics, commentators, designers and the like are starting off with a semi-satirical OPH-meets-Hollywood view of “prep”. They don’t know the real thing, which is somewhat flexible in the parameter anyhow, and are simply in reaction against a poorly identified group that they haven’t met in person.

    Remember, these are people who use terms like “normcore”, “workwear”, “mom jeans”, etc. as if they were legal or technical terms of art, and who think “street cred” is something to be proud of.

  6. Just Sayin' | August 19, 2018 at 10:30 pm |

    Too bad the only Ivy Style commenter quoted was that bigot, whose objection to the blazer-wearer was not-so-subtly racist rather than simply classist/elitist/school-ist. Ivy Style seems to be the most right-leaning of Ivy sites out there, at least as far as the comments are concerned, but there’s a variety here as everywhere, and it’s too bad the core demographic for the style is being further pigeonholed into one regrettable stereotype.

  7. Jordan Mitchell | August 20, 2018 at 12:58 am |

    For those readers who, like me, were unaware of the existence of DNR, the publication mentioned by CC, here’s the DNR obit from 2008:


  8. Caustic Man | August 20, 2018 at 6:24 am |

    The article suggests that preppy is being rebranded to stand for being happy and doing the right thing rather than aspirational wealth. If you add a dash of communitarian conviction and a concern for the greater good isn’t that what the highest ideals of the Eastern elite were about anyway? Perhaps prep is getting back to its roots, albeit in a roundabout way.

  9. whiskeydent | August 20, 2018 at 8:09 am |

    I’m amused that “Christopher Horsford” criticizes the Rowing Blazers models as posers and, by extension, questions Carlson’s legitimacy in the sport of rowing.

    Per Wikipedia: “Jack Carlson (born May 22, 1987) is an American rowing coxswain and author. He represented the United States at three World Championships, and won a bronze medal at the 2015 World Rowing Championships in Aiguebelette, France.[1]”

    Who’s the poser now?

  10. Mitchell S. | August 20, 2018 at 9:05 am |

    Preppy clothing is becoming more egalitarian at the same time that the colleges and universities which inspired the preppy trend are becoming more competitive, expensive, and exclusive.

    This tension between fantasy and reality creates social anxiety and blurring of the
    line between authentic and fake. One can see this clearly in the New Arrivals section at Polo.com: items featuring fake club crests are sold with products featuring authentic university logos.

    Authentic preppies are probably laughing behind the backs of posers wearing the Polo “Letterman Cardigan.” To paraphrase French Montana in “Famous,” the problem with faking it until you make it is that you’re fake when you make it.

  11. FWIW, I think that Christopher Hosford, quoted above, was decrying people who wore uni and club blazers and patches that were unearned.

    I wouldn’t wear a Yale sweatshirt, much less an Oxford rowing club blazer

  12. If only J. Press would focus on great cloth, top drawer tailoring, and classic styling.

  13. Caustic Man (as I type your nom de plume I realize that maybe you were using it to issue a warning),

    I hope you’re right about “preppy” taking a roundabout route back to its beginnings when it was the uniform of the WASP, who were (despite their many well-documented shortcomings) at least sincere in their, as you so charmingly put it, “communitarian conviction” and “concern for the greater good” and becoming the uniform of a new generation of likeminded folks, of whatever ethnic and/or religious affiliations. That’s the most hopeful thought I’ve seen about the future of “preppy.” Let us make it so.


  14. whiskeydent | August 20, 2018 at 5:36 pm |

    I was raised Presbyterian, but I do not think WASPS’s have the market cornered on greater good. I don’t know of a major religion — including Islam — that doesn’t call on its followers to serve the entire community. The question is what that service should be?

    However, there are some fundamentalist and evangelical ministers whose idea of service to the community is to be it’s scold. That, and making sure there’s cash for the Lear.

    • @whiskeydent,

      I agree. WASPs, or the Eastern Establishment as Caustic Man put it, were a convenient (and perhaps the prime) example of that injunction to serve the community given that they populated the Ivy League schools that begat the Ivy look, which became “preppy” or “trad.” For me at least dressing that way signals that same sense of self-worth beyond net worth and a calling to serve.

      Wasn’t trying to imply that WASPs had the market cornered, apologies if that’s how it read.


  15. SE: Who cares who’s making Jack’s blazers? Will that really determine whether you buy one? For that matter, why do you care what Press does? You’ve already decided that buying rtw from retailers is silly when you can buy custom online, so what’s it to you? A word of caution, the more people think like you and do everything they can to avoid paying towards an ever shrinking retail margin, the more retailers will fold up, and when rtw retailers disappear, the factories lose their biggest clients (for instance, did you know Southwick keeps the lights on largely bc of, drumroll, Allen Edmonds, and that despite companies like Ratio and Michael Spencer popping up, Garland continues to lose money hand over foot?)

    Maybe it’s time you relaxed. No one is forcing you to buy anything (clearly) so maybe just let it go and enjoy the stuff you already have. Or keep at it and help chip away at American manufacturing. Your choice.

  16. Jonathan Wertheim | August 21, 2018 at 12:00 pm |

    @whiskeydent – indeed. Don’t forget the Jesuits!

    @LED – Michael Spencer shirts are made in Garland, I believe. So I doubt Garland is losing money *because* of them, even if it’s struggling. (I don’t know offhand where Ratio makes their shirts.) And Southwick is owned by Brooks Brothers – I’m not entirely clear on how the AE connection you mentioned works.

  17. Vern Trotter | August 21, 2018 at 12:59 pm |

    Yes, how does Allen Edmonds, based in Wisconsin, affect Southwick, in Lawrence/Haverhill MA, and owned by BB?

  18. whiskeydent | August 21, 2018 at 1:02 pm |

    I’m curious about the AE thing too. Different owners and products.

  19. Vern Trotter | August 21, 2018 at 1:36 pm |

    AE is owned by Caleres, formerly Brown Shoe Company of St. Louis, maybe the oldest shoe maker in the US. I see no connection at all.

  20. Southwick makes apparel for AE. A lot.
    Garland shirts makes for Ratio and Michael spencer. All of it.
    Take away the money that Southwick/Garland make from big retailers, no more capacity to make for small custom-only companies.
    Make sense?

  21. AE has an “apparel” division?

  22. Jonathan Wertheim | August 21, 2018 at 5:50 pm |

    @LED – “Take away the money that Southwick/Garland make from big retailers, no more capacity to make for small custom-only companies.” Well, obviously. Translated, you’re simply saying, “Take the money away from the factory, and they can no longer support their business.”

    But the question remains – is Garland losing money despite those companies, or because of them? Your comments aren’t consistent with each other. I think you misunderstood S.E.’s original point, anyway, or at least read a lot into it. S.E. was asking if Greenfield makes the blazers – an American small business, just like the Garland factory. Not entirely sure where your irritation comes from there.

  23. Garland loses money despite the business of small one-off custom websites like the two mentioned. It and Southwick depends on places like J Press or Allen Edmonds or whoever else uses them for rtw to buy enough that it can depend on that income and keep the lights on (or at least convince Brooks Brothers to keep paying the electric bill) Not sure why that wasn’t clear for you. Here’s my larger point in a nutshell: obsessive dissection and dissemination of who makes what and where you can find it cheaper will slowly kill retail locations operated by bigger companies like AE, companies that are manufacturers’ most reliable source of income. Shrinking margins mean smaller buys mean less income for manufacturers means it’s more likely they’ll close, and that means no more American-made custom clothing for websites like MS/Ratio/Epaulet/etc

    And like I said who cares who’s making the Rowing Blazers…blazers? What does that information get you? If you like it and you’re cool with the price, buy it. That’s all. And SE is the last person who needs to know any of this bc he’s said he doesn’t buy any of it anyway. There’s some of us that do buy and aren’t offended that places like j press want to try something new to get non-octogenarians in the door so THEY can keep the lights on.
    As my Jewish grandfather would say, capisce boychik?

  24. Vern Trotter | August 21, 2018 at 9:14 pm |

    AE is selling men’s clothing on their home site. Nearly all on sale. Very little looks like it would be made by Southwick. Maybe there is more here than we thought but I doubt it totals much.

  25. The AE store here in Chicago sells AE branded clothing and Baracuta Jackets.

  26. Jonathan Wertheim | August 22, 2018 at 12:15 am |

    @LED – Dude, chill. Simply wondering who makes the blazers isn’t exactly “obsessive dissection and dissemination of who makes what and where you can find it cheaper.” That was never in S.E.’s original comments as far as I could see. It’s great that you’re passionate about this, but your response is not in proportion to what was being said.

    I still haven’t seen hard evidence that Southwick makes anything for AE. They are owned by Brooks Brothers, so they aren’t convincing Brooks to do anything – Brooks has already stated publicaly it will take a loss to keep work in Garland, and I assume the same goes for Southwick or else they would have offloaded it by now.

    The one who seems to care most about this whole non-issue is you.

  27. Jonathan Wertheim | August 22, 2018 at 12:15 am |


  28. “And like I said who cares who’s making the Rowing Blazers…blazers? What does that information get you? If you like it and you’re cool with the price, buy it. That’s all.”

    I don’t disagree with you. If a customer is fine with the price tag and doesn’t require any information beyond the fit and look, then, by all means, go for it.

    This said, we know that plenty of reputable retailers are pleased to share information about their manufacturers/makers. If the “private label” crowd lose business because of a lack of information, then, well, that’s their choice. Most of the better men’s shops I know of are quite pleased to share the names of their brands (lines). It makes sense. Exhibits A and B:



    If a company that specializes in blazers chooses to withhold the name of the manufacturer, that’s his/her/their choice. But, in a market saturated with retailers who are pleased to provide as much information as possible about manufacturers, I don’t think the question can be deemed inappropriate, out of line, or uncalled for.

    It’s a difficult situation, to be sure. Consider the great brands (manufacturers) of old that are no more: Norman Hilton and Troy Guild to name just a couple. I’ll agree that it’s extraordinarily difficult to keep up quality and meet the demands of retailers (and their customers). Your plea for a cease-and-desist noted, I’m not sure there’s a way back. There’s so much information available nowadays–about which manufacturers make what. And how well.

  29. Calling people “dude” on the internet is in my top ten for lamest things ever

    SE sees my point, JW not so much. All good! Like I said being an educated consumer is awesome, but there are consequences. Wm King and O’Connells are pretty small and benefit from attaching the Southwick name to their stuff, can Cable Car compete? SF rent is too high to cut their margins anymore, what’s the end result?

    May we all chill and may this continue to be a non-issue dude

  30. elder prep | March 8, 2019 at 7:09 pm |

    Is the gentleman in the striped rugby and matching trim shorts a member of the German football club? The colors are correct.

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