Thursday, August 6, 2026

A Reader Question: Updating the Preppy/Ivy/Sloane Lifecycle Chart

A Reader question:

Good morning, my memory lane guru and tour guide.  
One of my favorite posts remains your 2017 introduction to the "Life Cycle of Preppy Companies."  ("Many peddle aspirational vulgarity." Brilliant.) 
I was wondering if you plan a 'ten years on' update - I think it would be well received! 
All the best from this New Englander in his Mid-Atlantic exile,

So, with the goal of filling in an updated chart:

From your experiences, focused on clothing and accessory companies that fall roughly in the Preppy/Ivy/Sloane lane, and for Men and Women, which companies would you include on the chart today, and in which category?

Chart Designed by Salt Water New England

Examples of Past Companies and 2017 Placements, according to SWNE readers

    Crucible to Precious
    Iconic
    New Markets
    • Le Tricoteur <https://letricoteur.co/> 
    Cash Grab to Company Shell

    And the original 2014 chart here <link>.

    The broad characteristics of each stage are as follows (and all characteristics won't apply to all companies):

    Crucible
    • A company serves demanding clients in authentic environments significantly better then competitors.  
    • The company’s founder is hands on.
    • Products rapidly evolve, with dozens of failed prototypes.  The company typically does one thing very well. 
    • Marketing is not done.
    • Other people often love the products without necessarily recognizing the company that made it.
    • As any VC knows, companies here are highly unstable; they can change nearly instantly, from experiencing overnight rapid growth, to selling out, pivoting, or going away.
    • Not all start-ups begin in the crucible stage.  
    Precious
    • Fiercely passionate customers, who are "in the know," are very loyal to the company.
    • The company has much higher prices than competitors, which fans are happy to pay.  Prices are fair and constant, and when a new variation on an older product is 20% more expensive, for example, the product will be worth 20% more.

    Precious companies have much higher prices than competitors, which fans are happy to pay.  Marketing is poor, and not a priority.  Web sites may be disastrous.

    • Quality is paramount. 
    • Customers can still call or email and get the owner (and often work through any problems).
    • New, great products are added, seemingly effortlessly.  The company has an aesthetic certainty, neither derivative nor capricious.  
    Iconic
    • The company has widely recognized popular and unique items.
    • Great pride is taken in the company by employees, who go "beyond the call of duty" to make happy customers.
    • Items are expensive, but high quality.
    • New items, extensions of old, are added.
    • Companies gain increasing brand recognition well beyond passionate base.

    Iconic companies worry about becoming trendy and stylish, something that cash grab companies are desperate to be. 

      • The company worries about becoming trendy and stylish.  They also fear complacency, bloat, and smugness, and don't want to be thought of as the category leader.  They sell great products, not a great brand.
      • A short term flattening of growth can cause panic.
      New Markets
      • The company is often under new management, typically with MBA and logistics-centric credentials. The company increases focuses on greatly improving contribution margins, often in association with new investment money.  
      • The new management begins to purge many of the old employees and suppliers/branded vendors that had contributed to the success of the company. 
      • Companies feel entitled to their traditional customers and markets. Companies in this stage are very interested in new categories of customers, and take the existing customer base for granted; many loyal customers find themselves buying less and less.
      • The new management experiments with "leveraging the look and the feel of the brand and brand experience" by tentatively lowering the quality and increasing the channels, supported by ramped up marketing, including social media.   Cheaper parts are swapped in wherever possible.
      • Marketing gets increasingly - often awkwardly - self-congratulatory.
      • The company makes big deals of changing the colors of successful products.  
      • Vendors open ancillary stores, for example, in this stage, which do not yet influence design decision making.  
      • No new great products are launched, despite expensive misfires.  Companies go after markets they don't understand.  From a marketing and design perspective, the company becomes derivative, dated, and piecemeal. 
      Cash Grab
      • There is a nearly impossible to resist opportunity for upper management to personally cash-in with a one-time windfall through a rapid market expansion with much lower quality goods at still high prices with very high margins, irrevocably sacrificing brand, long-term employees and partners, and traditional customers.  In other words, transforming nothing into a great company is somewhat profitable. Transforming a great company into nothing is highly profitable.
      • Companies believe success comes when they can best distract from, rather than highlight, what they are actually selling.  Many peddle aspirational vulgarity.
      • There is significant confusion from traditional customers.  Long time customers start to experience return-fatigue.
      • Some classics remain (but fewer and fewer).
      • There are wild fluctuations of prices (higher prices, then massive sales, with various coupons and sweepstakes).
      • New products are low quality and relatively expensive.  Companies design for 75% to 80% mark ups.
      • Ancillary stores grow in influence over the direction of the company. Outlet stores open. Companies here may invest in "big data" programs.  The culture embraces short cuts to short term success.
      • Companies increasingly outsource production to low-cost providers.
      • Companies are desperate to be stylish and trendy.
      • A cash grab company further increase their PR budget, first spent trying to differentiate the company from their past and pushing new, very-high-margin products, then relentlessly trying to invoke their heritage when the new products flop.  The term "iconic" is used.  A lot.  Companies become louder and more strident. 
      Company Shell
      • The company's new owners think they can market their way out of their dropping sales.
      • Companies' products are no longer significantly differentiated in the marketplace. Branding chugs along.  Companies here find themselves with new competitors and engage in a race-to-the-bottom in quality to shore up crumbling margins.
      • They shift, almost overnight from an external market perception, from relevant and interesting to irrelevant, tired, and over-exposed.  
      • Outlet stores and other bottom feeding strategies become highly influential in setting company strategies.  
      • Company shells use old black and white photographs that have no connection to the current organization.
      • They rely on good customer service to overcome quality problems, not to meet individual needs or repair but to efficiently replace or refund.  Guarantees become more restrictive.  Finally, customer service, typically the last point of pride and holdover from the once strong company, fades to squeeze out a few more dollars of profit.


      29 comments:

      1. Only time will tell!

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      2. Perhaps I’m missing something. The description of New Markets doesn’t appear to match up with many of the listed brands. Brooks Brothers? Yes. J.Press? No.

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      3. In the film business we call this "room tone"

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      4. I am really shocked at how quickly J. Press went from Precious to Cash Grab. Their ad campaign (yes, they have one) is unbearable. Daily emails promoting new products, and of course the inevitable SALE that comes with a massive influx of products that no one wants.

        I don’t personally shop there, but I would add O’Connell’s to the precious category. I think the overwhelming chaos of their website is a contributing reason to why I haven’t purchased anything from them haha.

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        Replies
        1. J Press is definitely Cash Grab at this point...I recently bought similar items from J Press and Sunspel. The Sunspel item was far better quality...and $50 less expensive!

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        2. Ivy Style has a useful current interview with Jack Carlson of Press.

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        3. A few points:
          I have one broadcloth shirt from O'Connells and J.Press each, and the quality is high and roughly equal.
          I am certain that Mercer shirts are better than those from J.Press and O'Connell's, but they are significantly more expensive.
          I own an O'Connells suit and it is excellent.
          I own a J.Press Harris tweed and it's excellent.
          Prices at O'Connell's are usually 5-10% higher than at J.Press.
          Criticizing a retailer for marketing and another for the quality of its website is self-refuting; websites are marketing.

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        4. From what little I've bought from J. Press, I think that the quality of their staple item--their OCBD--is impressively high for the money. They are well constructed in the U.S.A. using thick cotton, along with little added features like the iconic (sorry!) chest pocket and locker loop are not free to include in the production process.

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      5. I stop reading whenever I see the word "iconic." There's a relationship between the ubiquity of "iconic" and the decline in the quality of everything. There's a certain mentality at work. A few years ago, no one said or wrote "iconic.." Now it's the default adjective for anything or anyone known to more than three people. Already today I've seen it applied to a mud flap, a retired table tennis player, a spatula, and a tampon. Enough already.

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        Replies
        1. I've seen the word Ionic applied to a column in front of a building.

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        2. I’m interested in which words you would use in place of crucible, precious and iconic. Perhaps you could dazzle us with your use of the English language?

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      6. I have no idea how this fits into the scheme, but I do know I have things I have liked a long time, and they are still up to my expectations: Mercer for shirts, certainly; Harley sweaters from Bosie, of course; casual shoes from Quoddy and Rancourt, yup; dress shoes from Shoemart are Alden; belts from Everlasting on Etsy; house brands suits, jackets, and trousers from flannels to khakis at O'Connell's; and vintage Chipp and Southwick on Etsy. I know some fastidious souls will quibble with these choices, but they remain my picks. I read about places like Press and Brooks recommitting to their heritages and shake my head. It is an all or nothing proposition they are not prepared to undertake.

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      7. Follow-up on above post on Ivy Style interview with J Press current president Jack Carlson? Any opinions?

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        Replies
        1. Just this morning, J. Press sent out an email advertising their new “vintage-inspired Yale t-shirts”. I would say that about sums it up.

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        2. They know the magic words, but they are unable to follow them assiduously.

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      8. J Press jumped the shark when they started doing those "x" collaborations with trendy fashion designers.

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      9. Excellent analysis!
        I have been a very loyal Barbour customer since I was a teenager. Now, at 56, I see my favorite outerwear brand undergoing exactly what this analysis describes. Back when I was 12 or 13—in 1982—very few people in my country, Spain, wore Barbour (unless they were hunters or traveled frequently to the UK). Over the years, the brand became very popular here, then declined, stabilized, saw a resurgence, and raised its prices; they were no longer found in hunting shops but in shopping malls. Then, about four or five years ago, they began a series of increasingly absurd collaborations. They have attracted new, "trendier" customers, but have lost many of their loyal users who no longer care for these "novelties" and experiments...

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      10. I miss what Filson used to be. Once the VC money moved in, the brand lost both its core customer as well as it's history and reputation.

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        1. I recently went to their website to get a bag for my son, the site is essentially what I'm calling "cowboy J Crew" now. I don't remember the volume of products, especially the logo-wear.... The 48 hour Duffel that I purchased was lighter and had a very different feel than the one I've owned for years. Only time will tell if it holds up but I suspect I know the answer.

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        2. Glory be - your comment raised my curiosity. I just looked at the Filson website. $45 for a mesh cap. Who is buying this stuff? “Cowboy J Crew”
          is perfect.

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        3. Good question. Add in tax and delivery, You’re probably pushing $60 for a faux outdoorsy/logger/look at me mountain man-woman mesh cap. Better to go on a shopping spree upstate at Stewart’s and get the real thing for half the price.

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      11. Enshittification in the retail world.

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      12. I couldn't agree more re: both Filson and Orvis! I spent a lot of money with each over the years, but those days are long gone. Orvis has been ruined for years. It must have made sense to someone to turn everything into some sort of "Tech" garment, but I find that it's nothing but cheap junk. I never even bother to look at the website any more. I still peek at Filson occasionally, but the emphasis has clearly gone from producing high quality outdoor gear into something that only works for bearded guys pretending they've set foot in the woods once or twice.

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      13. I somewhat disagree about Filson. I have bought quite a lot of Filson product in the last 15 years and have never been disappointed. I have a large Twill Duffle that is over a decade old that gets stuffed with clothes 3 or 4 times a year and has survived Air France, French TGVs and car trips. The only thing is it will never develop Patina in my lifetime. I also have a Tin Cloth duffle bought last year that has the same high quality.

        I bought a Chameau/ Filson tote 20 years ago and it has been my go to most of that time. The Chameau rubber has been torn a bit but the Tin cloth has years left.

        A Bristol Cardigan is the best sweater I own, and should stop me buying a new sweater every year. I have 3 Waffle Henleys that at age 3 seem almost new and last year I bought one of those J Crew Cowboy hats people are ridiculing and it is twice the hat Polo sells for the same price. I also bought a Seattle wool Jac Shirt last year that is perfect for the Vancouver winters.

        Full disclosure I am not a logger or a guide and I can’t speak to what Filson was in the 60s but I doubt others that are criticizing Filson can either.

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      14. Filson used to make a piece of luggage that was sort of - like the ones used to transport a suit. It folded over. It was very sturdy. I used the strap to carry the bag over my shoulder. My hands were always free. I often was able to pack it till it bulged on all sides and was still able to fit it into the overhead storage bin. It served me very well on many trips to the Horn of Africa, God’s joke on man. Then I hit 70, 4 years ago. I gave in and bought a “wheelie bag.” My daughter said it was “a major lifestyle change.” It was. Now, in the back of my mind is always the fear one of the #*+¥|~ wheels will break. I never had to worry about that with the Filson.

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      15. I have purchased multiple dress shirts from J. Press when they had their custom shirt offering. Great quality but otherwise, their site is full of items that are not in stock. O'Connell's always seems to have a wide range in stock. I am a native Seattleite and Filson is not the same. At the old flagship store you could watch the workers contructing their clothing and other items. Now most of the items are made overseas. Eddie Bauer went the same route long before. A damn shame for both brands.

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      16. Following the passing of its founder, Private White VC is a shadow of its former self. The range has been reduced substantially and design standards have dropped.

        Gant is trying to rediscover its Ivy heritage but the new Yale collaboration is naff. Fortunately, there are some top quality shirts, albeit at a higher price, this autumn. They are made from Thomas Mason cloth and have real pearl buttons. The quality and value are much better than rip-off PRL.

        I used to be a Huntsman customer but….

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