What’s The Preppiest Thing You Own?

In the spirit of the recent feature at Ralph Lauren Magazine, what’s the preppiest thing you own?

For me, it’s probably a custom blazer from J. Press. That and Ivy-Style.com.

You? — CC

Image from Scot Meacham Wood

80 Comments on "What’s The Preppiest Thing You Own?"

  1. Michael Horton | March 1, 2019 at 2:03 pm |

    LL Bean Duck Shoes. Oh, and ten pairs of khakis (in various states of wear).

  2. Richard E. Press | March 1, 2019 at 2:06 pm |

    Back to the well. My prep school yearbooks from Loomis.

  3. Two pairs of Ralph Lauren GTH pants. One with geese flying in formation and one with bees. Going into RL’s one day the salesman actually wanted to buy a pair off me ! And ‘lest I forget, my third Mercer and Sons shirt, just arrived this week.

  4. My patch Madras shirt from Polo with flap pocket in the style of J. Press.

    I saw the shirt featured on Ivy Style, so many thanks to you Christian.

  5. Robert Staehling | March 1, 2019 at 2:24 pm |

    I reckon the preppiest things I own are my Bean Boots and my Brooks ties

  6. whiskeydent | March 1, 2019 at 2:27 pm |

    Bean boots, deck shoes and too many repp ties.

  7. A B.A. in classics from a SLAC.

  8. Dutch Uncle | March 1, 2019 at 3:06 pm |

    Fortunately, I don’t own anything “preppy”, but the Traddest things I own are my nearly identical navy knit ties, khaki chinos, and blue OCBDs.

  9. Charlottesville | March 1, 2019 at 3:08 pm |

    Ratty Barbour jacket from 1990 and a couple of pre-M&S Brooks Brother OCBDs.

  10. I owned a pair of Bass penny loafers made in USA.

  11. Sorry, I mean I own a pair of Bass penny loafers made in USA

  12. Sartresky | March 1, 2019 at 3:27 pm |

    Matching Yale ’49 and Cornell ’81 beer steins, one from my father and the other my own.

  13. MacMcConnell | March 1, 2019 at 3:33 pm |

    My wardrobe, except in reality it owns me.

  14. My Letterman sweater from Avon Old Farms.

  15. Hardbopper | March 1, 2019 at 3:35 pm |

    Like Dutch Uncle, more trad (conservative) than prep. And like you, CC, a custom flannel blazer. Also BB ties and long-wings.

  16. Would that I still had my ‘83 Volvo DL; that would be my answer.

    As it is, my big answer is a house along the water on an island – it always feels like Nantucket West. My little answer is my Gant madras jacket.

  17. Minimalist Trad | March 1, 2019 at 3:39 pm |

    My Anglo-American Optical tortoise eyeglass frames in P3 shape. Style no. AA406.

  18. Undarted 3-button sack blazer and a few more sack sportcoats by J Press plus some vintage Brooks Brothers with unfused and unlined collar and cuffs and transparent plastic buttons.

  19. Jack at RB owns an original 1979 “Are You A Preppie?” poster…

  20. Ditto, Mr. Press. Ne Cede Malis!

  21. I have two — for some reason — first editions (the 1980 paperback) of the OPH, both dogeared and well-worn, naturally.

  22. AtlantaPete | March 1, 2019 at 4:27 pm |

    Early ’90s Brooks made to measure suits from the days Nick Fiorello ran the tailoring operations in my town – the bastards fired him shortly before his retirement after 40 years of service.

  23. Trevor Jones | March 1, 2019 at 4:30 pm |

    A non-iron, black OCBD with a 2.5” collar. Right up there with my cotton-stretch skinny chinos and square-toed loafers.
    Wait a minute, wrong thread….

  24. Trevor Jones | March 1, 2019 at 4:32 pm |

    ….I’m sorry, but I couldn’t help myself. Seeing as I’ve stirred up some lively debate as of late, I thought I’d keep things fun.
    Have a good weekend, all.

  25. For A/W it has to be my Bean Boots, and for S/S my ridiculously comfortable patchwork madras pants from BB.

  26. My golden retriever !

  27. NaturalShoulder | March 1, 2019 at 5:15 pm |

    A Ralph Lauren 20th anniversary polo purchased new in 1987 which doesn’t really fit but I still hang onto for sentimental reasons.

  28. Roger Sack | March 1, 2019 at 5:29 pm |

    Silk ecru pleated evening shirt from Chipp, circa 1964.
    Doesn’t fit anymore. Also have a green glenn plaid RTW suit
    from J Press that is two button w/ side vents and natural shoulders
    circa 1970. A departure from their sack suit paradigm. If I recall
    correctly, around that time I saw Richard Press at their NY shop
    wearing a similar cut with turn back cuffs a la Savile Row.

  29. Trace Bearden | March 1, 2019 at 5:32 pm |

    Vintage Nantucket Reds trousers from Murray’s, found in a charity shop for $5 (perfect fit). Vintage wood lacrosse sticks from the 1940s..

  30. Angloamerican76 | March 1, 2019 at 5:55 pm |

    My great-grandfather’s 1913 Vanderbilt letterman’s sweater.

  31. MacMcConnell | March 1, 2019 at 5:59 pm |

    Rethinking the most preppy thing I own would be a RL Polo stadium blanket from the mid 1970s. It’s got to be considered preppy because it’s fun and obnoxious. It is six foot plus square, thick cotton & wool, red and navy. One side has a huge red Polo logo (player & pony) with a navy ground, the other side the colors are reversed.

    In keeping with the Scot Meacham Wood image above, I’ve got two ladies RL Polo scarves from the 1970s framed and hanging in my office.

  32. john carlos | March 1, 2019 at 7:03 pm |

    3 pair of “New Old Stock” plain front madras trousers from Oconnell’s purchased about 15 years ago. The real deal with vegetable dye.

  33. Terry O’Reilly | March 1, 2019 at 7:35 pm |

    My cottage on Nantucket.

  34. From 1980, ‘The Official Preppy Handbook’

  35. My white polo shirt with blue pony by RL.

  36. Thomas Long | March 1, 2019 at 8:28 pm |

    My 3/2 roll bleeding madras sport coat from Frank Leonard, a heyday era collegiate clothier from Baltimore, MD.

  37. elder prep | March 1, 2019 at 9:02 pm |

    As FJW and RBM noted above, my 1980 first edition of the OPH. Also, my 1970 canary yellow Triumph TR-6, my mechanical mistress.

    P.S. Does anyone know if Lisa B. published the OPM in hardbound?

  38. john carlos | March 1, 2019 at 9:48 pm |

    Elder Prep, I’m a 69 years young prep. Are you more elder than me?

  39. Joel Vaughan | March 1, 2019 at 11:56 pm |

    Pair of older J Crew faded Nantucket reds, with on-seam pockets, and embroidered whales, bought at thrift

  40. A closet full of vintage Brooks and J. Press but I guess the best is a I954 XK 140 FHC

  41. elder prep, I’m guessing that your question is regarding the OPH? Yes, there was a hc gift edition, it came in a red box sleeve. They show up on eBay on occasion, nice copies sell for about a hundred. I remember seeing a huge stack of them on a clearance table at a big box bookstore back in ‘82; they were about ten dollars. I bought one, but it’s gone missing over the years.

  42. @elder prep

    Just Google Official Preppy Handbook hardbound (or hard cover):


  43. Prescott Fortescue | March 2, 2019 at 3:16 am |

    For those who’ve never had the pleasure of reading the book, here it is in its entirety:


  44. René Lebenthal | March 2, 2019 at 3:30 am |

    My wardrobe, especially a bunch of JKeydge Ivy jackets
    but most of all Maybe my Alfa Romeo Spider 2.0 which I own now for almost 30 years

  45. Addison DeWitt | March 2, 2019 at 7:27 am |

    A pair of BB cordovan tassels and a BB Baracuta-style pig-suede jacket, both circa 1983. I still frequently wear the shoes, the jacket only occasionally. I also have a Tiffany sterling silver, engined-turned, hand engraved money clip that I have been using since 1980.

  46. Harvard bow tie.

  47. Khaki pants and white OCBDs.

  48. elder prep | March 2, 2019 at 10:55 am |

    Thanks all for the reference to the HB edition of the OPH. My SB copy is nearing the end of its useful reference life and I plan to have it inturned with me for additional reference and enjoyment in the afterlife, wherever that may be. To answer another poster, I turned 70 in July, the ides of July, to be exact.

  49. Hinckley Picnic Boat.

  50. My dad’s pop-over from the 50’s. He, and then I, almost worn it out but I retired it in the late 1980’s and now only use it as the pattern for my tailor to copy.

  51. Beverly Carlton | March 2, 2019 at 11:29 am |

    Columbia lightweight crew varsity jacket, earned during endless early morning rows on the filthy Harlem River. Or a Masters green 3/2 sack Golden Fleece blazer.

  52. Bravo Beverly!

  53. Lest there be any confusion, though I’m sure the HC is nice, the SC of 1980 IS the true first edition of the OPH (and decidedly more preppy, anyway, than a ‘presentation edition’ in a sleeve; although, of course, the HC will fit the bill in terms of durability into the future).

    @Mylman, anything Hinckley is outstanding, alas all I can claim is an old navy polo with the Hinckley ‘H’ in white on the breast, and a navy ball cap with the same, both of which I love.

  54. Poison Ivy Leaguer | March 2, 2019 at 1:32 pm |

    For this crowd I believe the least preppy thing might be a more interesting question. I’ll start it off. My black Wrangler jeans from Wal-Mart and my “off road” Crocs (tie.)

  55. Old School Tie | March 2, 2019 at 1:50 pm |

    JLC Reverso.

  56. A Black Watch tartan waistcoat from Brooks Brothers.

  57. Brooks oxford, alden loafers, and my initial belt.

  58. Bill Stephenson | March 2, 2019 at 2:18 pm |

    Everything I own. Been at it since you could do no wrong at BB. Then fled to Press, and gave up when Richard was forced out. Now, Mercer, O’connells, and Oxford for suits and jackets made as they should be. Time has forced a few changes. Golden retriever died, and had to replace Volvo box wagon with a Subaru. Moved from a prep community (Princeton) to Oklahoma city, where going sock less is like leaving your fly unzipped.

  59. Two copies of the OPH.

    That, and a vintage Co-op blue Harvard tie from the 1960s. Legitimize wearing it, and a navy blazer with the Harvard crest, by having completed several free Harvard edx classes.

    As Sonny Drysdale would say, “A handsome Harvard man.”

  60. @Poison Ivr Leaguer

    I was thinking along the same line as you. The only thing I have that is not preppy/trad is my Zero Halliburton aluminum briefcase and my Under Armor Tactical running togs. I’ve read somewhere that distance running is not considered preppy/trad. Got ten miles in today. Good for the soul.



  61. Probably the teddy bear my grandmother made me – a birthday gift sometime in the mid 80’s. She took the patch madras RL button-down I wore during my freshman year (until too small) and made the bear body from it with the polo pony in the appropriate location. A treasure and favorite keepsake. Other items: LL Bean field watch and a pair of RayBan aviators ordered from Bean catalog in ’82. This was pre-logo on the lens.

  62. Roger Sack | March 2, 2019 at 7:28 pm |

    Moved from a prep community (Princeton) to Oklahoma city, where going sock less is like leaving your fly unzipped.

    Is that because sooners confuse appendages?

  63. Jesse Livermore | March 2, 2019 at 8:20 pm |

    A cute blonde named “Muffy”.

  64. Theo Loewe | March 2, 2019 at 11:46 pm |

    A manual Royal typewriter, received as a high school graduation present in 1960, and used for papers, an MA thesis, and a PhD dissertation—all at Princeton. The typewriter was used while wearing one of many blue OCBDs bought from the on-campus University Store. And yes they had collars that ranged between 3” and 3 1/4”.

  65. Dennis Welcher | March 3, 2019 at 10:13 am |

    My 36 year old blue Gloverall duffle coat … it should last forever now that I live in Florida

  66. A circa 1930’s beret produced by Brooks Brothers for the boys at my prep school with the school’s emblem sewn on. It was a gift from my father in law. It’s way too small and I would never wear it, but a nice keepsake.

  67. Another super preppy item that I love is my green/pink madras pocket square from BB.

  68. Four grosgrain ribbon watchbands from Brooks Brothers that I wear with a $35.00 Timex watch.

  69. Baracuta jacket and my english pipe collection ,still smoked on weekends !

  70. All the gear my husband keeps from his father P34 and mother.We have books, clothing, smoking pipes, silver, rugs, tables etc.Throw in the fishing rods, Buffalo check old LL Bean jackets and silk scarfs. All this is charming but a nightmare to pack and move yet again. I stuff the Volvo wagon and haul the canoe on top. Lots of paper memorabilia in cartons. I almost forgot, the family skeletons are priceless and the prep no one EVER mentions.

  71. My house in Grosse Pointe Michigan.

  72. Evan Everhart | March 4, 2019 at 10:05 am |

    I have 3 very old Brooks Brother made school ties from The Hill School, plus my Father’s and Grandfather’s ancient madder ties from White’s of New Haven and elsewhere in that vicinity. I think those take the cake over my old RL socks.

  73. Evan Everhart | March 4, 2019 at 10:19 am |

    @ Poison Ivy Leaguer: Yr a crack up, Sir! I’m game: least preppy items in my possession: a collection of vintage Western boots, a very elaborately carved vintage Western style belt with a silver buckle, a Stetson Open Road in natural, and an old Pendleton blanket jacket for the Winters that I used to spend with my Aunt on her ranch, and my visits to family in Texas and (some of the family in) S. Dakota.

  74. MATTHEW M VOLLMERS | March 4, 2019 at 2:24 pm |

    My Earl Whitney’s Hudson Bay Point Blankets. Way too many to count, Two for the Master Bedroom One for each Bedroom, a couple for the Family Room, two for the Basement Rec Room, Several colors, but at least 6 of the iconic White with Four Color Stripes.

  75. Jeffrey S. Haber | March 4, 2019 at 2:26 pm |

    My Fall and Winter J. Press Brochure from 1964 along with the Fall and Winter Brochure of 1981(a great year- as I worked part-time that year at J.Press alongside my father, the late Jerry Haber- who was a wonderful salesman). And one more thing, I happen to have “The Official Preppy Handbook”, Edited by Lisa Birnbach. This 1980 paperback edition of that famous handbook sold for $4.95 back then.

  76. Jeffrey, my first edition SB version of the OPH book has its $3.95 price in the upper right corner cover. Compare that with what Amazon is asking for a copy nowadays.

  77. Jeffrey S. Haber | March 13, 2019 at 8:32 pm |

    Thank you for your report elder prep. The OPH Book(that I own) is unquestionably a gem and I intend to hold onto it indefinitely.

  78. Some Brooks Brothers socks, a Ralph Lauren shirt and some sweaters. Latin dictionary and Bible. Anglican Missal. My New Yorkers and volume of John Cheever’s short stories. And of course, my pedigree, which goes back to colonial Massachusetts, Maryland and Pennsylvania.

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