Neo-Prep Lives At The Harriman Cup


While I was away in Cape Cod last week, my new “nephew” Al Castiel III crashed at my place so he could attend the Harriman Cup polo tournament on Long Island. What he found was that neo-prep lives, with Harriman putting the H in GTH. Here’s his insufferable report. — CC

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Early last Saturday morning, a gaggle of pastel-clad preppies descended upon New York’s Penn Station. No, there wasn’t an impromptu clambake going down in the Gate 2 waiting area — The 32nd Annual Harriman Cup was about to begin. In a swirl of Nantucket Red and lime green, everyone rushed onto the Long Island Railroad with their LL Bean totes filled with Rose and Veuve for a booze-filled ride. On the train, drinks flowed while other passengers confusedly looked on and scratched their heads. Though, if the LIRR wasn’t up to your standards, you could always use Blade to fly into the match on a helicopter at $275 per seat.

As the respective UVA and Yale polo teams took to the field, the spectators seemed none the wiser. The match was more of a backdrop than anything to the social aspect of the event. Madras, seersucker, Ralph Lauren, Hermes, and Lilly Pulitzer were worn with reckless abandon, with ladies in pairs of Jack Rogers sandals reaching the hundreds in number.

The Harriman Cup acts as a sort of last hurrah of sorts to break out the summer wardrobe in epic (and purposefully garish) proportions, while drinking, tailgating, and dancing during the after-party were all in order. In addition to the cup itself, awards were given for the best-dressed man, woman and couple; best tailgate; best dog; best hat; and best fascinator (still trying to figure that one out). Sponsors included BASK with its piped terrycloth blazers; JP Crickets, maker of velvet slippers; and E. Vogel, bespoke bootmakers, among others. The society gossip site GuestofaGuest was naturally there snapping photos.

In between taking full advantage of the unlimited buffet and bar under the VIP tent [Editor’s note: please explain] and doing an impromptu interview for TheStreet on my outfit choice for the event, I managed to snap a few photos of some looks that caught my eye.

First up is Mark, last year’s best-dressed winner, sporting a vintage Lilly Pulitzer blazer and Stubbs & Wootton slippers, paired with pink shorts. He regularly peruses eBay for go-to-hell blazers from Chipp and Lilly. He discovered Chipp after attending the FIT Ivy Style Symposium, where he also learned of this site.



This young gentleman decided to buck tradition and go for an ascot as instead of a necktie:


Rob in full neo-prep regalia in his Thom Browne rowing-inspired blazer and Vineyard Vines necktie. He’s one of the few technically allowed to wear a rowing blazer (even one by Thom Browne!), as he rowed at University of St. Andrews.


On the right is lifestyle blogger Dean, formerly of the blog ProperkidProblems, staying impartial showing his love for both teams, with friends Josh and Greyson, sporting such items as suede Belgian Shoes and a neckerchief.


FE Castleberry was at the match as well, sporting a seersucker jacket from his new made-to-measure label and some Jackson-Pollock inspired cutoff shorts.


Finally, yours truly (top photo) sported my father’s Ray-Bans from 1982, a go-to-hell jacket from The Andover Shop, Sid Mashburn shirt, and Bass saddle oxfords.

Oh, and UVA took the cup. Not that anyone noticed. — AC3

64 Comments on "Neo-Prep Lives At The Harriman Cup"

  1. Whoah, didn’t recognize Fred at all! Thom Browne-inspired haircut?

  2. Outrageous costumes!

  3. My gosh I’ll be happy when skinny pants are gone.

  4. Wow. Fred looks like a Travis Bickle from Taxi Driver.

  5. Manorexia is the new madras.

  6. See, now this is why millennials are the ubiquitous brunt recipients of so much sartorial obloquy. Their panache and insouciance is admirable if it were not so ersatz. On a side note, (and completely out of the other side of my mouth) I have been wanting to try JPCrickets; anyone have an opinion on sizing?

  7. Is “sizing” kind of like “shirting” and “suiting”?

  8. Al is the only one who is dressed GTH but not douchey. There’s a fine line between the two and it seems everyone else crossed it.

  9. Marc Chevalier | September 25, 2016 at 2:02 pm |

    If Pitti Peacocks were Ivy….

  10. Marc Chevalier | September 25, 2016 at 2:05 pm |

    @WFBjr, @Christian: “Sizing is any one of numerous substances that is applied to, or incorporated into, other materials — especially papers and textiles — to act as a protective filler or glaze. Sizing is used in papermaking and textile manufacturing to change the absorption and wear characteristics of those materials.”

  11. There is no such thing as “Neo-Prep”. Exept for Al Castiel III (He´s neat as always.), we see ill fitting clothes. For example, most of the shirt sleeves are too short (or the jacket sleeves too long). The Jackets are too short, the lapels too narrow, the shirts and trousers are too tight. Don´t get me startet about the jacket pattern. A nightmare. Prep gone horribly wrong.

  12. @AGCC “Prep gone horribly wrong” is the very definition of Neo-Prep.

  13. Also, I wholeheartedly agree with the specter of the late William F. Buckley Jr., thank you for taking time out of being dead to give us your insight.

  14. Great piece, Al! Hope yo had a nice time there.

  15. Again, Al’s style is not my own, but he’s the only guy in the bunch who doesn’t look cartoonish – he looks good. And that train sounds like the ride from hell, frankly.

  16. The difference isn’t just fit and item combos, I think. Al has spent a lot of time with Charlie Davidson and just finished interning under Mark Rykken at Paul Stuart. I think he’s interested in being well dressed according to the traditions going back to the golden age of the ’30s and as chronicled in the writings of Frazier, Flusser and Boyer.

    The other guys have a fashion/ironic sensibility, not timeless standards of what it means to be well dressed. The difference in sensibilities is what accounts for the difference in fit and taste and therefore the entire outfit.

  17. Gentlemen: whatever you do, if you click CC’s “irony meter” link above, don’t limit yourself to just the first video; let the whole series play; it’s amazing stuff.

  18. Wait, there’s more?

  19. Oh yes – how Ferd originally came to NYC to work in “finance”, but – of course – was quickly bored with it and went into fashion.

  20. Chewco L.P. (Cayman) | September 25, 2016 at 6:47 pm |

    Irony Part II:

    But anyway, Thom Browne… at Target? That jacket costs $150? Get outta town! Brand Dilution 101 by Prof. Browne.

  21. Actually those fashion designer collections for Target or H&M are hugely successful. Remember Lilly for Target? Sold out in 5 minutes.

  22. If we’re seeing the same video, Paul, FEC doesn’t say he did finance in NY, though it’s visually misleading because there’s a shot of the Empire State Building, not Texas.

  23. “Let’s go make a living doing finance and business. After five years of that, I was bored out of my mind.”

    Now, he could be making a fool of us all – as far as I know, he was Lloyd’s right-hand man.

    Still …

  24. @FEC
    Where does one get the Jiminy Glick eyeglasses?

  25. Chewco L.P. (Cayman) | September 25, 2016 at 8:19 pm |

    Christian, You’re right about Lily.

    Ok it is clear that people like to poke fun at FEC, but I have to be honest in saying that I am quite impressed with what he’s doing with his business. Because it is extremely difficult and so far he seems to be holding up, I am forced to take him seriously.

    However, those are some stupid f*cking glasses and its hard to take a man seriously who wears presumably non-prescription glasses with lenses the size of those designed for octogenarians in the 1960s (a period of time when technology in optometry was still altricial).

    He has no excuse. None.

  26. Let’s not be pedantic over the use of “sizing.” Are they true to size?….

  27. Hah, gotcha, pedant!

    Speaking of language usage, “reactionary” for “reactive” in sports broadcasting is spreaing like a plague….

  28. Unrelated to this article, just read that Arnold Palmer passed away. What do you have to say of his style on the green, Christian? I’ve seen many old pictures of him in cardigans and polo shirts, typical 50’s golf wear but nice.

  29. Anglophile Trad | September 26, 2016 at 1:33 am |

    The Harriman Cup commemorates the life and work of the late Averell Harriman, former governor of New York and ambassador to Great Britain and the Soviet Union. The way that these clowns dressed is an insult to his memory and his sense of style:

  30. The Ferrigamo and Hermes belts are completely vulgar. Parvenu at best.

  31. Giovanni Casarossa | September 26, 2016 at 1:53 am |

    Admittedly, Mr. Castiel’s outfit does not belong to the same category as the clownish-outfits in the other photos, but wouldn’t saddle shoes be more appropriate without a necktie?

  32. Enjoyed this feature. I think Al should do more of these.

  33. Al is in a league of his own.

  34. And it’s waist not waste Marty.

  35. Charlottesville | September 26, 2016 at 10:53 am |

    Funny/sad. Remarkable what passes for “prep” these days. As others have pointed out, Al is the only one who does not look like a jackass. By the way, a fascinator is a small decorative hat worn by women for effect, rather than for warmth or sun protection, and as for anyone caring who took the cup, I do. UVA also won its weekend football game for a change, so September has not been a total write-off in the world or local sports.

  36. Swanning around in Cyberspace one can find more pictures from the Harriman Cup.

    Perhaps the ultimate style question for events like this is whether or not one should wear shell cordovan shoes to an event where horses are present.

  37. Mark, the one with the koala blazer- I know him from Notre Dame, he was amongst the most hated people on campus during his tenure. Most outfits were on the side more of costume than style. Bad person, bad style…

  38. The Loafer Lawyer | September 26, 2016 at 12:31 pm |

    A hearty Wahoowa. Harriman Cup and a football victory. I dare say the football victory was possibly more rare. The Fall Foxfield Races were run this past Sunday as well. The sartorial tastes at this bi-annual Steeplechase in Charlottesville are typically a bit more traditional, though the Spring Races often feature just a little too much youthful exuberance in the tailgating. Missed the fall race, which I prefer, this time around.

  39. This post is the gift that keeps on giving: I just watched the linked interview and, as hoped, Al comes across as very funny and as self-deprecating as one can be when describing one’s tailor; when he takes the mic was especially amusing.

    Also: in this day and age, am I allowed to say that the interviewer in the Lilly dress ticks off all the boxes in my Jewish girl fantasy? Oy.

  40. That’s problematic, as was Al’s denying her voice and microinvalidating her by taking the mic with his male privilege.

  41. Actually, Christian, he was mansplaining. Disgusting display of chauvinism.

  42. Al looks great, true to his own taste and having fun. The others just look sad, and worse, dated. Like they showed up for a preppy costume party 5 years too late. 2009 called guys, it sends its apologies and wants the skinny jeans back.

  43. If the plan was to make the paint splatters on the khaki cutoffs look natural, you have failed. I don’t believe Picasso ever got that much paint on his pants.


  44. “The others just look sad, and worse, dated. Like they showed up for a preppy costume party 5 years too late. 2009 called guys, it sends its apologies and wants the skinny jeans back.”-DCG

    the millennial fogey speaks truth.

  45. My math is more poetic than exact if you couldn’t tell…

  46. Charlottesville | September 26, 2016 at 1:51 pm |

    @Loafer Lawyer – I missed Foxfield as well. Too crowded, and a bit too amateur-hour-at-the-bar these days for me. Or maybe I’m just getting too old for it. Last time I went, I recall navy blazers, Nantucket reds, bowties and penny loafers (at least that’s what I wore), but I haven’t been lately. Hopefully the current scene is not as costumey as the pictures above. And congratulations and welcome back to Mr. and Mrs. Fogey.

  47. The Loafer Lawyer | September 26, 2016 at 4:24 pm |

    @Charlottesville – The Spring Foxfield is the bacchanalia that I am too old to enjoy. Fall, in that it is on a Sunday, is mildly more subdued. You are right in the sartorial choices, though cowboy boots and a smattering of GTH sport coats were also de rigueur, along with sundresses for the ladies. The Montpelier Hunt Races (Nov. 5), in neighboring Orange County, are a bit more sedate (or at least less overrun by 18-22 year-olds), but less prep-attired.

  48. I’m sensing some common experiences here: in an earlier life, I enjoyed the Point-to-Point races at Winterthur, which is the old duPont family estate in Delaware, they tended to be masses of 20-somethings in wild colored clothes getting obliterated, until they fixed the problem by simply doubling the admission price (as I recall, tailgate spots were raised to $400/per). Years later older and [hopefully] wiser, my local shindig (south of Annapolis) was called “Roedown”, and was still country steeple-chasing, but a bit more mature, a bit less gingham and self-conscious “prep”, and more actual horse-people.

  49. One more sartorial inquiry, echoing another commenter: what is with tight, white, above-the-ankle jeans on men? The only way to look more effeminate would be to wear an actual skirt.

  50. Charlottesville | September 26, 2016 at 5:13 pm |

    Paul — I’m with you on the ludicrous painted-on jeans on the boys above. Please leave those to the young ladies. Has anybody been to the Virginia Gold Cup in The Plains lately. That was quite an event when I was living in Washington, but I have not been in many years. At least in the old days, people behaved themselves (within reason) and dressed fairly well. Blazers and sundresses were the norm, and the tailgating was at a pretty high level.

  51. Roger C. Russell II | September 26, 2016 at 10:08 pm |

    They are all rather flamboyant. Al is in the spirit of things, but remains sensibly put together. However the neo-prep look a few of these guys have is just too contrived. It comes off more as a bad costume rather than a stylish statement.

  52. Still waiting for someone to be politically incorrect enough to use the terms “Gay Ivy” or “Gigolo Ivy”.

  53. Actually I was rather hoping we’d avoid corny terms that are not only insulting to well-dressed gay men and entrepreneurial male escorts, but also painfully un-witty. Just reading the word “gigolo” makes me shudder with its cheesiness. BE MORE WITTY.

  54. Chewco L.P. (Offshore) | September 27, 2016 at 9:35 am |


    I was at Gold Cup this year. Comparable to Fox Fields, just a more adult crowd. Naturally, because of this they tended to have more $, be a bit more mature, and therefore, in my opinion, better dressed (from what I can remember). There’s a place there called “Member’s Hill,” and like most private clubs, you just have to pay a fee to get in 😉 It provides a good vantage point for the actual race (if you’re into that sort of thing) and of the wonderful ladies decked out in full regalia.

    I might be switching from Fox Fields to Gold Cup henceforth.

    It was quite muddy this year. Should have worn boots and def. not pearly white trousers 🙁

  55. Marc Chevalier | September 27, 2016 at 10:31 am |

    @DCG: I dub them “Poison Ivy”.

  56. Charlottesville | September 27, 2016 at 10:33 am |

    Chewco – Gold Cup sounds as pleasantly grown-up as I recall it. I really should make an effort next spring. The closest I have been to a race in the past few years is having cocktails with my wife while watching the neighbor’s horses graze. Soothing, of course, but not quite as festive.

  57. I have to dissent on one. I agree most of the men pictured look clownish. But “Mark…sporting a vintage Lilly Pulitzer blazer” looked good. Except for the shoes.

  58. Ed: black “invisible” socks visibly poking out of his slippers, and a visor?

    Waste of nice vintage Lilly P. Sad!

  59. @Fogey: you left out the gold chain around his neck – sexy!

    PS – congrats on the nuptials.

  60. I did not even see the gold chain. Yikes. And I did see the visor and shook my head when I saw it, but forget about it already when I posted. Still, I liked the jacket and short color combo.

  61. @khaki chino

    Rather like proclaiming grass to be green or chinos to be…well, khaki, no?


  62. It looks as though the person sitting to the right of the fellow with the black footie socks and sun visor is anxious for everybody to know that his coat is from Aquascutum.

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