St Johns Bay Rum Giveaway: Describe The Ultimate Preppy GTH Outfit

If you’ve wondered what 16 months of lockdown would do to the narcissistic personality types who work in fashion, the answer is here.

Vogue recently ran a slideshow of the menswear shows in Paris, and the anarchic outfits validate everything said by Edward Gibbon, Camille Paglia and everyone else who’s ever opined about the chaos that ensues when traditional norms are trampled underfoot by platform boots.

You can find the 150-image slideshow here. It’s difficult to select the most outrageous outfit, since each is more improbable than the last, but these should give you the gist:

Needless to say, the slideshow got me thinking. About a lot of things, actually, but let’s pick one.

Say a trad guy — you, for example — were sent by Ivy Style to cover the Paris menswear shows. You hear that the latest trend is “anything goes” and you want to keep in the spirit of things, but you also want to stay true to yourself, so you come up with the idea of wearing the ultimate go-to-hell outfit. What would it be?

Here’s what I came up with:

Lug-soled bit loafers with Black Watch tartan pajama bottoms cut off at the knee to show lederhosen
Critter belt, white OCBD unbuttoned with collar pin, patchwork madras tie
Vintage alpaca cardigan under a motorcycle jacket under a rowing blazer
Bucket hat, Wayfarers, wife’s purse

If you’re new to our giveaway contests, it’s quite simple. Submit your entry by leaving a comment; be sure to use a valid email so we can contact you if you win. Winner will be chosen by random number generator. The prize is a bottle of cologne of your choice, graciously donated by St Johns Bay Rum:

This should be a fun one, so we’ll keep the contest open all week and close it Friday at midnight. — CC

24 Comments on "St Johns Bay Rum Giveaway: Describe The Ultimate Preppy GTH Outfit"

  1. I think that I would just make the stunning and brave step of wearing non-iron OCBD shirts for the trip.

  2. whiskeydent | June 28, 2021 at 5:15 pm |

    I’ll go with my current get-up: brand new tan linen guayabera, green linen shorts, decaying brown deck shoes (I refuse to call them boat shoes), no socks and a frown for the event. It’s a Texas trad kinda thing.

  3. My ultimate preppy GTH outfit:

    1. A case of “sprezzaturourette’s:”
    OCBD with collar flaps unbuttoned, bow tie messily tied, Orvis duck-embroidered chinos with the bottoms rolled up to reveal double monk strap shoes in chocolate brown suede with one strap on each shoe unbuckled.

    T-t-t-take that, c-c-c-coronavirus!

  4. A pair of Weejuns and nothing else.

  5. Spartacus | June 28, 2021 at 7:23 pm |

    The perfect unholy GTH outfit, now this is something.
    How about:

    First requirement is a pipe.
    Madras short sleeve shirt button down, with navy blue knit tie.
    Pants would be Bermuda shorts with whatever motif suits your fancy, sailing boats/skulls/Santa Claus in some compromising position reminiscent of Chipp’s.
    Knee-length argyle socks with some frayed Weejuns.

  6. Sprezzaturourette’s?

    The description of that reminds me of what once happened in graduate school.

    At the end of one semester, I was out late one night drinking. After about an hour of sleep, I had to wake up for an 8 AM meeting about grading that all the teaching assistants had to attend.

    I was in such bad shape that I managed to put on a polo shirt backwards.

    People just thought that it was part of some new trend that I was following.

    I’d expect the same reception for sprezzaturourette’s.

  7. CC for the win. Here’s second place, from head to toe:

    Some kind of tartan nightcap
    John Lennon’s purple lens sunglasses
    Tie dyed OCBD with sleeves cut to 3/4 length
    Houndstooth sport coat with sleeves cut off
    Paisley tie
    Braided belt worn extra long and tied in a knot instead of using buckle
    Extra baggy tuxedo pants
    Orange wallabee boots
    Silk purple knee high socks
    Plastic shopping bag

  8. Old Bostonian | June 28, 2021 at 11:17 pm |

    “Preppy” is, by its very nature, go-to-hell, for those of us with a truly Trad disposition.

  9. Willie Stewart | June 28, 2021 at 11:19 pm |

    -Dax Wave and Groom and Jeris Tonic in my hair.
    -Yellow and white butcher stripe dress shirt, no undershirt.
    -Red knitted emblematic Cocker Spaniel tie with a plain silver tie bar.
    -Drake’s Unicorn Pocket Square, TV fold.
    -Navy 3-Button Sack Model Tropical Wool Blazer.
    -Color 8 Shell Cordovan dress belt with trim fit grey tropical wool trousers, 1.75” cuff.
    -Corgi green and white University Stripe 100% cotton socks.
    -Shell Cordovan LHS Loafers tanned in a Argyle and Sutherland pattern.
    -St Johns Bay Rum on absolutely everything.

  10. Old School Tie | June 29, 2021 at 9:05 am |

    Jacket, madras. Stains, vindaloo. Pants, Prince of Wales. Underneath, Prince Albert. Shirt collar, unlined. Residue, white lines. Hat, Panama. Necktie, Columbian. Socks, argyle. Underwear, highlander. Cologne, bay. Watch, wound up. Shoes, worn out. Pipe, filled. Soul, empty.

  11. elder prep | June 29, 2021 at 11:30 am |

    The collection of images shows what happens to a certain set of people when confined for too long. Hopefully, by the end of summer, they will all have recovered and be back to normal Ivy and/or Prep style. Keyword: Hopefully.

  12. I think I would draw a bunch of tattoos on my body with crayon. That is all. Oh I would wear a boater hat.

  13. Norman4Law | June 29, 2021 at 4:12 pm |

    Tan shoes with pink shoe laces,
    A polka dot vest and man, oh, man,
    Tan shoes with pink shoe laces,
    And a big Panama with a purple hat band.

  14. Benjamin J. Dunnigan | July 1, 2021 at 8:54 am |

    A ballroom gown made of Murray’s Nantucket Red fabric. Done.

  15. White crocs with a red sole, a tartan wool kilt with a “Fuck Wasps” motif, Nantucket red corset, purple grosgrain suspenders, green vineyard vines tie, navy blazer which is cut at the waist and has a faux university embroidery on the back, topped off with long, bacon-grease hair.

  16. AndrewK247 | July 2, 2021 at 2:07 am |

    1. Hair – Princeton cut – dyed in Princeton black/orange stripes
    2. Monocle
    3. Ribbon belt (red white & blue) used as a necklace/choker
    4. Significantly oversized canary yellow Lacoste polo (with a safety pin through the crocodile), OVER a purple Shaggy Dog sweater
    5. Short pleated skirt in Blackwatch tartan, OVER blue uni stripe seersucker leggings
    6. Bit loafers with no socks – leather is lime green, bit is pink
    7. Hermes Birkin handbag, maroon colored with cream colored lettering that spells “HAVRAD”

  17. AndrewK247 | July 2, 2021 at 2:14 am |

    @ECMJ – Love the tartan nightcap and the plastic shopping bag! Hahahaha!

  18. @AndrewK247 – Thanks! Your “OVER a purple shaggy dog sweater” detail is hilarious!

  19. Charlottesville | July 2, 2021 at 11:09 am |

    These are so perfect. I expect to see all of this in a fashion spread any day now. While each comment hits the target squarely, my vote for most Pitti Uomo Vibe goes to AndrewK247. My only contribution is to note that Ralph Lauren’s actual 2018 and 2019 offerings contained some tough competition, as shown in these Ivy Style posts:

    http://www.ivy-style.com/forty-two-fall-2018-polo-rl-rhinelander-mannequins.html

    http://www.ivy-style.com/polo-fall-2018-encore-45-more-mannequins.html

    http://www.ivy-style.com/neoprep-revival-polo-rl-spring-2019.html

  20. Roger Sack | July 2, 2021 at 2:57 pm |

    In a well-ordered society the individuals depicted above
    would be rounded up and assigned to a (style) re-education
    center.

  21. GTH items aim to imply the wearer belongs to a different/exclusive social set. One the viewer is unaware and unwelcome in. Therefore wouldn’t the ultimate prep outfit reflect the opposite of the maximalism of Paris fashion shows?

    My pick
    Sweatshirt from your child’s prep school, worn out reds, and cracked weejuns.

  22. Henry Contestwinner | July 6, 2021 at 2:57 pm |

    Hair: dreadlock mullet with Afro along the sides. Various colors in the dreadlocks; Bozo the Clown red for Afro.
    Face: tattoos, and lipstick like Robert Smith of The Cure. Shave off eyebrows.
    Shirt: none. Just a button-down collar ripped from the body of the shirt, with the buttons sewn to the holes. Black Oxford cloth.
    Jacket: for the sleeves, the legs from a pair of seersucker pants with critters (lobsters having anthropomorphic sex). The “sleeves” should extend well past the fingers. Attach sleeves to body with safety pins. For the body, a patch Harris tweed jacket. Instead of hip pockets, attach Ziplock bags filled with water; add goldfish, guppies, etc.
    Sweater: draped over shoulders, a PRL teddy bear sweater. Add metal earrings, nose rings, etc. to the bear. Bear must be wearing something with skull & crossbones. Sweater must be unraveling at waist.
    Boutonniere: an unwashed leek.
    Timepiece: anything rejected by Flavor Flav as being “too big” and “too gaudy.”
    Underwear: a Borat-style mankini in hot pink.
    Below the waist: a Utilikilt in hunter orange/safety yellow plaid, with several bleach stains. Handsewn. Short enough to be in danger of revealing what ought not be seen in public.
    Hose: mismatched plastic shopping bags—one from Target, the other from Walmart. One (only one) is held up by a hidden garter which displays lavender “flash” (i.e., colored tabs, as once seen with knee socks on Boy Scout uniforms).
    Shoes: Crocs x Weejuns x Vans. 3″ platform soles. 4 3/8″ drop between heel & ball of foot.

  23. And the winner is whiskeydent

  24. whiskeydent | July 8, 2021 at 3:20 pm |

    You’ve got to be kidding. I never win this kind of thing. Thank you!

    If you tried to email me, it could have bounced because my email was down a few days. It works now.

    People have always said I stink but now I have a chance to do something about it.

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