Ivy Notes S1 E24

I saw sweaters for sale on Greenwich Avenue yesterday.  It is back to school time.  Which is weird because that used to be the third week of August.  Yet, here we are.

First, check out J. Press’s Pennant Label.   They USE the word “Ivy.”


Click on the image to check out the collection. Full on Ivy.


I have been toying with the idea of starting a discussion about Ivy Things I Can’t Pull Off.  For me, as bad as I want to, and I want to badly, I cannot do bucket hats.  And I have the best one.


The Sunken Ship is a store in Nantucket, but you don’t have to spend $1,000 a night to shop there. It is a souvenir shop, a legit fishing and beach store, and you can grab a Nantucket Bucket Hat for $19. By comparison, the Brooks Nantucket Bucket Hat is $125. Click on the image, check out the hat, but also check out the whole site.


They just don’t look right on me.  And they also get my vote for most bastardized (well, maybe the ballcap, but this is a mighty close second) Ivy element.  I don’t think you can consider the tie purely an Ivy element, so I am not including this.  VICE did a piece on the BEST bucket hats, and here is what they pick:


You read right. Best.


I started down the bucket hat rabbit hole because The Amazing Tom sent me a Times article about bucket hats.  It starts with a letter from a guy named “Jeffrey”.  “Jeffrey” is from London, but he has mighty American references.  “Jeffrey” has lupus and needs a hat.  “Jeffrey” writes the author, Ms. Vanessa Friedman:

But Ms. Friedman does a good job of running down the whole bucket hat deal.  Here is a link to the article:


This is Christian Louboutin at the French Open in June. Mr. Louboutin is a designer, not Ivy, but looks like a very pleasant person. Click here to read the story. I got ripped a little while ago for not including links to other stories that I didn’t write, MOST of them are behind paywalls so it gets REALLY annoying but let’s try it.


It’s Yale day here.  Here’s a more in line bucket hat if you like Yale, don’t like Nantucket, and are not at the French Open:


If you click, you go.


What Ivy Element do you think you can’t pull off?






32 Comments on "Ivy Notes S1 E24"

  1. whiskeydent | July 21, 2022 at 8:38 am |

    When it comes to bucket hats, my opinion can be expressed in just one word: Gilligan.

    • John Burton | July 21, 2022 at 9:08 am |

      Which, oddly enough, and I covered that here, is a very Ivy show. Ish.

      • whiskeydent | July 21, 2022 at 1:58 pm |

        To me, a bucket hat looks like it’s missing something. What is its practical use besides making you look dorky? Does it have any connection to an American or a British tradition? Where’d they come from? Can we put them back?

        I guess I hate the damn things more than I realized.

        • Gilligan wore a US Navy “Dixie cup” hat with the brim down. I’m not much of a hat historian (hatstotian?), but it seems like that could be the bucket hat origin.

  2. I would have to say anything that describes itself as “thin” or “slim” fitting.

  3. the passenger | July 21, 2022 at 9:41 am |

    1) The bucket is the only style of hat that doesn’t look good on me, so I understand where you’re coming from on this

    2) Jeffrey’s assertion that “…Fedortas, trilbys and Panamas seem to proclaim the wearer as either an extravagant nonconformist or an anti-feminist reactionary” reveals a lot about his own insecurities. I have half a dozen Panama hats, and none of them make me look like either of those. Maybe he just hasn’t found the right one yet? (I can, however, understand his reservations about the other styles.)

    • I own two Panama hats which I love wearing casually on sunny days and for travel. I bristle at the notion that wearing such a hat would mark me some kind of “men’s rights” goober. It’s the only kind of hat that I think looks plausible on my head. Book cover judging is inevitable, but nobody really knows your inner life or your views unless you share them. I do get Jeffrey’s reference, but we can’t cede our good sartorial choices to groups of the loudest jerks who happen to have adopted them.

  4. Nutmeg Andy | July 21, 2022 at 9:45 am |

    I have a dark tan colored nylon bucket hat that is very useful for active pursuits. It floats, so I wear it while in the ocean to protect my balding head. I wouldn’t wear it to work or with a sportcoat, but it doesn’t look out of place with a tennis shirt and shorts and that sort of thing. I don’t do the GTH type stuff, something about it rubs me the wrong way.

    • Agreed on GTH — that’s one Ivy genre (or is it more preppy than Ivy?) that I simply cannot pull off under any circumstances. Bully for those who can, but I keep my clothes critter-free.

  5. Hardbopper | July 21, 2022 at 9:48 am |

    1. Too many to list for me, which is why I’m more trad than Ivy.

    2. If given a choice between looking like a dork or being “proclaimed” an extravagant nonconformist or an anti-feminist reactionary, I freely choose, yea, I much prefer the latter.

    3. As for hats protecting one from the sun, nothing beats a straw cowboy hat. A Panama has its place…pretty stylish, as does the Fedora in fall or winter.

  6. Talk about worlds colliding… did not expect to see the OPIV logo on your front page this morning

  7. The only way I can wear a bucket hat without looking like Gilligan, as whiskeydent suggests above, is to flip up the back of the brim (if possible), and then it takes on a fedora-ish shape. Although I would definitely wear that Operation Ivy one featured in the first pic: I’ve always had a soft spot for old school, raw, punk.

    I don’t actually own any bucket hats, but I do have it’s cousin: white cotton, very broad-brimmed, sort of floppy, like you sometimes see cricket players wear, or sometimes NFL coaches at summer training camp.

    • Hardbopper | July 21, 2022 at 7:41 pm |

      I think what you are describing is called a floppy hat, a field hat, or a booney hat. Standard issue in desert cammo pattern. Easy to roll up and pack away, most unlike a straw cowboy hat. I see them in the bucket shape as well as with a rounded top, reminiscent of a pith helmet.

  8. The Stetson Fairway is a nice option for those who, like myself, like the idea of a bucket hat but can never quite seem to pull it off. It’s a pork pie / bucket hybrid, and looks great with many ivy-inspired outfits.


  9. Bob Denver indeed (aka college beatnik Maynard G. Krebs in The Many Loves of Dobie Gillis 1959-1963). And saddle shoes. They looked nice online but just didn’t work once on my feet. Several wearings 10+ years ago. Reminded me of saddle shoes worn by my little sister in the very early 1970s when parents still “dressed” their children for school. Donated my pair fairly short order to the local hospital affiliated thrift shop in the end. Like a good neighbor, they might still be there, since that was in the wilds of Central Illinois where no self-respecting farmer or insurance guy clad in a company logo fleece, and planted in an open office plan at Corporate South, would be caught dead in ’em. Or so I believe.

    Kind Regards,


    • “Reminded me of saddle shoes worn by my little sister in the very early 1970s when parents still “dressed” their children for school.”

      This sums up my personal dislike for saddle shoes perfectly. They almost always look either childish or costumey to me.

  10. I didn’t go to Yale. But I know plenty of Yale alums and it’s clear they all have one thing in common: they rarely if ever wear anything with Y A L E on it. Especially cardigans.

    Actually I’m surprised Onward has maintained the J. Press- Y A L E connection consistently throughout recent years. Interesting marketing/advertising choice. To be clear, I’m pro-elitism when it comes to nearly all forms and versions of intellectual snobbery (this is actually a form of populism but I digress) but the current anti-elites/elitism zeitgeist is damned strong (even among the children of the 1%) and grows stronger by the minute. I can’t imagine that, generally and long-term, this affiliation/connection serves this style well. I’m told (by people who are smarter than I am–no great achievement, this) that GenZ’s and GenAlpha’s (here they come) kinda-sorta detest anything and everything their Rolex-wearing, Beemer-driving, PoloRL’d grandparents favored.

    “The brand as class-signifying totem is dead” is probably a tad bit hyperbolic– but not for long, methinks. We’re just not emerging (waking up) from the haze of the most vigorous era of brand-based advertising. We’re just now learning that none of us care that “Chet owns a Jag, a Patek, and a Burberry.” Turns out we never did.

    It’ll serve J. Press well to drop all the Ivy League university affiliations — and try for elegance and cool. Onward won’t care about my opinion but 50s-era, Ivy-covered Americana has its limits.

  11. * edit:
    ‘We’re just ‘NOW’ emerging (waking up)…”

  12. addendum: I’d like to see J. Press move further-and-further toward a sort-of “Cool, old-fashioned yet quirky Fogey” vibe (think Wes Anderson) and away from this “Oh-uh, did we mention we’re near Y A L E ?!?!” thing, including the Hilfigerish (Giant “Y” instead of “H”) vibes that, well, turn the stomach. If “Preppy” is dead among the cool folk I know (it is), then something else has been emerging– an earthy, outdoorsy, rustic, even tweedy look that’s simultaneously homespun and urbane. The execs at Barbour were way ahead of the curve decades ago, and the higher-up’s at Filson and Campbell’s of Beauty have caught on.

  13. *Beauly, rather

  14. Nothing wrong with them per se, but bucket hats are not Ivy. At least as far as canonical items go. Same with baseball caps, I suppose, but the bucket hat is even further afield in my opinion. Not that they don’t have their charm, in theory, but 90% of the time I am reminded of the old joke from Vice about how they are just “rap fedoras.”

  15. When it comes to hats, the narrower the brim, the less likely it is that I can pull it off. Fortunately, Portland’s mostly-trad retailer, John Helmer, has an abundant selection of hats with which to make comparisons. I’ve definitely learned what works for me and what doesn’t during my too-infrequent visits to the shop.

    I suppose one thing I always feel conspicuous wearing and don’t really believe I can pull off is my old pair of Sperry Topsiders. I’ve had them for at least 15 years or so. For the extremely rare occasion that I’m on a sailboat, I suppose I’ll be glad to have them, but I’m otherwise not the sort who looks or feels right wearing those things.

    Another thing is that I have a partiality to dark colors and do wear black loafers and black Lacoste polo shirts rather often, which I understand is a major Ivy no-no, but it’s the erstwhile New Yorker in me who can’t see myself wearing bright colors on any but the hottest of summer days.

  16. whiskeydent | July 21, 2022 at 4:49 pm |

    Re: what Ivy thing I can’t pull off: bow ties. One never looks right on me, perhaps because of my thick neck, big head, awful knot work, and an embarrassed expression on my face. You can put lipstick on a pig all you want, but it will still be a pig.

  17. Best use of a bucket hat in a film: Jim Hutton in “Where The Boys Are”. And he played a dork but at least got Paula Prentiss.

  18. NaturalShoulder | July 21, 2022 at 5:57 pm |

    I have never been much of a hat wearer other than baseball hats when attending games or now out in sun for extended periods of time now that hair is thinning in one spot. I did pick up a Irish tweed flat cap and plan to wear in the winter (wish it will come sooner in Texas given 100+ temps we are having).

  19. Hardbopper | July 21, 2022 at 7:52 pm |

    Funny, I heard the title theme from that movie at lunch today. Connie Francis. 12/8, a lot like the title theme from A Summer Place. Sandra Dee.

    • Hardbopper | July 21, 2022 at 7:55 pm |


    • I love both the Connie Francis song and the theme from A Summer Place. There is a kind of midcentury saccharine melancholy to both pieces that I find very affecting.

  20. I’ve owned a few over the years, from early teens to late…let’s not go there.
    I know they never looked “Kooool”, but that is kinda their appeal. They do the job. I’ve lived in D.C., N.C., Florida and Southern California, all places where at some point you definitely need a headcover. There is no way that they can be mistaken for “in” or even particularly attractive, just really good workers.

  21. Much to my chagrin, with the exception of an occasional cap, I cannot pull off hats in general. I can’t put my finger on why (maybe facial shape) but none really seem to look ‘right’ on me.

  22. MacMcConnell | August 30, 2022 at 10:50 am |

    I believe mil issue boonie caps are just flat top bucket hats. At least that’s what my marine nephew wore in Afghanistan and Iraq tours.
    I believe you are referring to something like these,

    I own one or two. Actually, in the 1960s and 1970s it was easy to find these in tan poplin sold in “Ivy” shops. We didn’t call them bucket hats, they were rain caps. The hat usually had a grosgrain hat band.

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