I Tried to Make the Apple Watch Ivy; It Isn’t

By Jim Moore

Ivy Style contributor James Moore is the English Department Chair and Director of Squash Programs at Blair Academy in Blairstown, New Jersey. Jim is a graduate of Cornell University where he was a member of the squash team, the glee club, and the Delta Chi fraternity.

Adapting Technology to Ivy Style: An Exercise in Futility

I like watches, but I am not a Watch Guy. My friend, whom we’ll call Beekman, is a Watch Guy, and struggles to choose a favorite from his thirty or so timepieces that range from a quotidian quartz-driven Seiko to a Swiss triumph of mechanics and precious metals by Audemars-Piguet. Wherever we get together, I ask Beekman about the watch he’s wearing, or the latest addition to his collection. Beekman was a corporate lawyer in his working days, and it’s much more engaging to observe him giddily demonstrate what Watch Guys call a “complication” in his Patek Philippe than it was to try to keep up while he explained the structure of a special purpose acquisition vehicle.

Patek Philippe Officier, EMore98, CC BY-SA 4.0, via Wikimedia Commons

I have a collection of watches, too, but I have acquired them in a much less ambitious, strategic, and expensive manner; indeed, I have simply accumulated them over the years, rather than collected, and somehow now have, on my dresser, four. My watches range in age from about five to thirty-five years, in price from seventy to 350 dollars, and in formality from a Swiss Army chronograph to a silver-colored Hamilton tank with a deep navy leather band that I wear with sober hard-finished wool suits. It is a good Ivy-appropriate quartet, traditional in appearance and modest in price, and while Beekman and I would both enjoy having him supervise my purchase, through his sources, of a six thousand dollar Omega Speedmaster, I’m happy with what I’ve got and equally happy to hold onto the six grand.

Hamilton American Classic Boulton Mechanical

Now here’s the thing: I have a fifth watch, which I am compelled by my interest in health and fitness to wear at some point every day. It is, of course, an Apple Watch, the most basic recommended by Wirecutter, that allows me to track my exertions on my bicycle and the track, in the gym, and on the squash court; it also, as it will do sometime in the next ten minutes, advises me to stand up and walk around. (I won’t elaborate on why I feel this need to measure and be reminded of such things but suffice it to say that maintaining one’s physical well-being in one’s seventh decade requires a different sort of attention than it did in the first six.) The Apple Watch is great at helping me stay focused on these important activities, but what it’s not at all good at is accessorizing Ivy clothing, and so I leave it on its charger when I’m not actually using it for something. And then I don’t get credit for all the steps I take during the day, which drives me nuts.

https://www.nytimes.com/wirecutter/reviews/best-smartwatch-iphone/ (Ruthie Darling/NYT Wirecutter)

I can tell that Beekman, the Watch Guy, regards the Apple Watch with cordial disdain, and he’s kind enough to observe that “whatever watch makes you happy is the best watch.” “Brian,” an absurdly fit colleague of mine, considers the Apple Watch simply another screen that threatens to consume his time and attention, which would be better spent lifting or playing tennis. (Somewhere between me and Beekman on the analog watch spectrum, Brian has amassed a small collection of Shinola pieces, the prices of which are close enough to what I consider reasonable that I have considered getting one myself.) On the other hand, our colleague “Endicott,” who is Ivy-educated but eschews OCBDs for the trimly tailored spread-collar shirts he has made whenever he goes to Hong Kong, wears an Apple Watch with an attractive aftermarket band, and it looks fine with the style of clothing he wears.

https://longvadon.com/blogs/blog/how-to-wear-apple-watch-with-suit (Toni Koraza, June 07, 2021)

I have tried the obvious solutions. Many companies that make watch straps– and there are more than you’d think there’d be– offer the striped NATO or grosgrain bands we Ivy aficionados find appealing but configured to attach to an Apple Watch. Adding such a band softens the look, but at the end of the day, it’s still something on your wrist that emits light, rather than reflects it. Likewise, I have scrolled through the range of watch faces Apple has designed and found some attractively sporty, with lots of sub-dials, and others elegantly spare, with Roman numerals. Paired with the NATO band, the former might work nicely with a polo and shorts and bound to the wrist with a nice leather strap, the latter might show up reasonably well under tailoring. But at the end, neither truly rhymes with a sack coat and a beefy Oxford cloth.

Barton Watch Bands Apple Watch Two Piece NATO®style Watch Band

I have also tried the less obvious and, in retrospect, preposterous experiment: wearing an analog watch at my wrist and the Apple Watch next to it, at the narrow part of my forearm. This arrangement required I keep my shirtsleeves buttoned at the cuff, rather than rolled up, to hide the Apple Watch. While this approach sort of worked because I was wearing tailoring, and the real watch peeped out appropriately from under my cuff, it also made me self-conscious all morning, which, you will recognize, is hardly conducive to feeling Ivy. Accordingly, I removed the Apple Watch before noon, stuffed it in my pocket, and immediately felt a rush of well-being. Discretion being the better part of valor, I did not even try the associated tactic of wearing an analog watch on one wrist and the Apple Watch on the other.

https://www.hodinkee.com/articles/double-wristing-a-guide-for-the-perplexed

The truth about the silicon-based marvel that is the Apple Watch is that, like the laptop on which I write this, like the new iPhone to which I upgraded early this summer, it too shall pass. Unlike the analog field watch I bought back in 1991, when Eddie Bauer was still an outfitter of repute, it will ultimately fail to help me make my way through the day, even if I take good care of it. Unlike that Swiss Army watch, about twenty years old, it will not pass to one of my children when I have gone on to my reward. Unlike my other watches, which have, like all good Ivy things, joined a larger narrative as they age, it is only a tool, albeit a fine one. In the end, it will simply conk out one day, my exercise rings vanishing forever with its last blink, an event signifying only that it’s time for an upgrade.

Jim Moore’s watch collection.

 

14 Comments on "I Tried to Make the Apple Watch Ivy; It Isn’t"

  1. David Knatcal | September 19, 2026 at 2:06 pm |

    You have a Timex Weekender which is my go to watch. I have an assortment of NATO straps I switch in and out with it. It’s a great, simple, inexpensive watch. And I was happy with just having that until I discovered my Russian made Vostok Amphibia. I too am not a “watch guy” but for some reason this watch fascinated me and I find it wearing a little bit more than the Timex Weekender now.

  2. I used to be a watch guy, but I’m traveling a lot these days (retired), and nothing beats the convenience and usefulness of a smart watch. I’ve actually thought about bringing along an automatic, but bringing extra things when you travel generally isn’t a great idea.

  3. Jim
    Thank you for your great article on watches . I have the same problem as you do . I am not a watch snob and I do not think an Apple Watch is Ivy. Frist it hasn’t been around long enough to be vintage and it is rude. When you are having dinner and it tells you to stand ,no manners.I have 4 watches besides the Apple ,Rolex oyster gold and silver bracelet 1985,Timex expedition with a Press navy blue and white ribbon strap, Girard Perjure 1971 with black alligator strap and gold rim ,lastly a Swiss Victorinox field watch with rubber strap. To me those are IVY. my problem is never know which one to wear.

  4. That’s a nice little collection. What is maintenance like?

    • Minimal. I get the batteries changed when needed. Once I had to send the Swiss Army into a third party repair center because the second hand fell off; it wasn’t expensive, but it was a pain.

  5. An enjoyable read with which I concur. Nice watch collection too.

    Kind Sunday Regards,

    H-U

  6. Prodigal Prep | September 20, 2026 at 11:14 am |

    An Ivy-Style watch discussion. Most appropriate!

    The two Nato straps you show in your collection are essentials. I’m wearing the the same green/yellow/blue/red strap now as I write. This was from Rowing Blazers. It doesn’t seem to be available now on their website. The other strap is still available from BluShark and other suppliers.

    My go-to watch is a Timex Weekender. I also have a Casio on a Nato strap. I had to take the lugs off to get the strap on, so the straps aren’t interchangeable, but it’s “more Ivy” than the metal watchband it came with. So, we could widen the discussion about Apple watches to include whether cheap but utilitarian Casio watches are Ivy, provided that they’re on a Nato strap, of course.

  7. Watches and horology have a history of sparking some lively discussion here!

    Fitness tracking benefits aside, I’ll never understand how people from our particular community – who are willing to spend significant money on clothing with heritage, classic aesthetics, durability, brand provenance, etc. – cheap out when it comes to watches. There are so few things in life that are made to last forever and that your children and grandchildren will enjoy after you’re gone. I don’t think a man needs a collection, but every man should have one classically-styled mechanical watch. I personally have a steel Rolex Datejust (smooth bezel, oyster bracelet configuration) and a rose gold Cartier Tank. Don’t get me wrong – many days, depending on what I’m wearing, you’ll catch me wearing a Timex Ironman.

    Very tempted by the recent re-issue of the Breitling Navitimer worn by Ivy stalwart Miles Davis.

    Looking forward to further comments.

    • You make a rational point, and, to be sure, the Omega Speedmaster is something I could probably figure out how to justify, despite the expense. (I also think more often than I should about trading in my very capable and stylish Fujifilm X-E3 for a Leica, but can’t get my head around the eye-watering price.)

    • Rolex white dial Turn-O-Graph and 25 year-old Timex “Deployment” watch here. 24 hour, 2 time-zones. Looking for an identical Timex replacement.

  8. Charlottesville | September 21, 2026 at 1:20 pm |

    Thank you, Mr. Moore. Like you and some of the other commenters, I am not really a watch guy, but I like wearing them and have acquired a few, somewhat haphazardly over the years. My father wore a Hamilton watch when I was growing up, and I have continued on that path. I now have 4 Hamiltons, along with an old military-style steel Wittnauer, all on leather bands, and a Timex on a grosgrain band. My favorites are at least 60 years old and still look great and keep perfect time.

  9. As for watch styles in general, I’m sure glad that the pornographic, big-dial craze seems to have receeded a bit.

  10. Lisa Birnbach cemented the Timex watch as a cornerstone of Ivy/prep style. Instead of an expensive luxury status symbol, the handbook championed an old, unpretentious men’s Timex paired with a colorful striped grosgrain ribbon band.

    • Matthew Longcore | September 22, 2026 at 9:33 pm |

      Craig, excellent point. I agree completely. The simple inexpensive watch with a grograin ribbon band is the epitome of Ivy/prep style. I remember vididly the first time I observed this. I was in my early 20s and being treated for a lower back injury by an orthopedic surgeon. He was a tall, lanky, distinguished looking gentleman with a Social Register pedigree – a graduate of St. Paul’s School, Harvard, and Columbia Medical School. He always wore bow ties with his OCBDs, and his watch (probably a Timex) with the grograin ribbon band was exactly as you have described. Years later, my father gave me this Yale watch as a graduation gift. It retains the same understated character of the Timex and it is the only watch I own.

      https://www.mlahart.com/collections/yale-best-sellers/products/yale-mens-collegiate-watch-w-raf-nylon-strap

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