What Would One Wear: Six Watches for Kendall Roy of Succession

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In the recent few weeks, there has been quite a strong interest on the watches that the cast of HBO’s wildly-popular series Succession is wearing on the show.

This gave us an idea. While our articles have often been focusing on selecting some of the best watches for our readers (based on specific themes and complications), we thought that it might perhaps be interesting to select watches for a particular fictional persona, based on what he or she likes (and dislikes).

Since there is quite a strong following on Succession, and that the watches featured in the drama had caught the attention of watch geeks, we thought we might want to start this series with a character from the programme. And boy, we do have the perfect candidate for this.

Kendall Roy of Succession

Connor Roy (Left) and Kendall Roy (Right). Image courtesy of David M. Russell and Robb Report.

Kendall Roy, played by Jeremy Strong, is the second-oldest child of Logan Roy. The Roy family manages Waystar Co, a media conglomerate, which can be said to be inspired by Rupert Murdoch and his media business empire.

In the first season, Kendall was poised to take over his father’s business. However, as the show progresses, we saw Kendall falling out of favour with his father. The deterioration had shaped Kendall into another character altogether, as Kendall lost his position in the family business and no longer operates as a key executive there. This also meant a change in lifestyle and behaviour subsequently (whilst still maintaining his wealth).

Since the fallout, Kendall has swapped the business suits out for more casual outfits – which includes designer shades, bomber jackets, and denim jeans. Hip is perhaps the word for his sense of fashion in the later seasons. For the more eagle-eyed viewers, Kendall’s wrist game has been quite compelling as well – he was seen wearing Richard Mille, Vacheron Constantin, and Patek Philippe watches on several occasions. This makes him the perfect candidate for us in this new series, where we will select a few watches that we think will suit the fictional persona.

So, without any further ado, here are the six watches that we think will be a good fit for Kendall Roy.

Bvlgari Octo Finissimo Automatic

We begin our selection with one of the crowd favourites: Bvlgari’s Octo Finissimo Automatic.

The Bvlgari is an apt choice for Kendall, who is often seen in bomber jackets and designer shades from Jacques Marie Mage. Kendall appears to be fashionable, although arguably, with a little bit of eccentricity. The Octo Finissimo, in our opinion, is the perfect watch that will help to ensure that he remains stylish, with its sleek and sharp geometric design.

Another interesting thing to note is that despite its popularity, the Octo Finissimo is still not considered to be a “mainstream” timepiece. This is also something that we believe Kendall will like, as we like to think that he tends to gravitate towards items (including watches) which are less common. Our pick is the base Octo Finissimo Automatic, in titanium, which retails at S$22,200.

Blancpain Fifty Fathoms

Next up, we have another excellent but uncommon timepiece. Cue the Blancpain Fifty Fathoms.

The Fifty Fathoms is arguably the granddaddy of modern divers’ watch. The unidirectional bezel, a hallmark of most divers’ watches today, is pioneered by this manufacturer. We opine that the Fifty Fathoms, with its chunky bezel and utilitarian design, offers a strong wrist presence – which we reckon works rather well with Kendall’s style and choice of dressing, which leans towards the casual side.

There are numerous variants of the Fifty Fathoms, and one of our favourites is the 500-piece limited edition “Tribute to Fifty Fathom MIL-SPEC” (pictured above). Although we believe this particular edition is no longer available, we do reckon that the base model, with a 45mm case, does the job brilliantly as well. Prices for the Fifty Fathom Automatique begin at S$23,200.

Hublot Big Bang Sang Bleu

Hublot may not necessarily be the first choice for many collectors, but that does not mean that they do not produce some interesting pieces. The Big Bang Sang Bleu is an example of that.

Produced in collaboration with Sang Bleu, a high-profile tattoo studio based in London, the watch aims to bridge the commonality between the two entities. The end result is an amazing timepiece that revolves around the themes of Leonardo da Vinci’s Vitruvian Man and the play of geometric shapes. Another recurring theme for the timepiece is proportions, which ensures that the watch looks amazing at different angles.

There is something cool about the original Big Bang Sang Bleu without being too ostentatious, and this should easily appeal to Kendall and his taste. Unfortunately, the original variant is limited to a production of 200 pieces, and all of them should have been accounted for by now (although it should be available in the secondary market). The watch was priced at US$18,800 (approximately S$25,385) when it debuted in 2017.

Ulysse Nardin Freak X

The Ulysse Nardin Freak is a game changer in the horological scene. First launched in 2001, the Freak was an experimental piece that brought us many different technological breakthroughs within the industry. It is not just about the geeky bits – it has an amazing architecture to match as well.

Extending the Freak line-up is the Freak X – a modern interpretation of the collection that was launched in 2019. The 43mm timepiece features a flying carousel and a super-lightweight balance wheel in silicium, reinforced with nickel flyweights and stabilising micro-blades. Overall, the Freak X still maintains the avant-garde look, but it is certainly a tad more palatable as compared to the polarising Freak.

There is something cool about the Freak collection, although most of the variants might prove to be too much for Kendall. The Freak X is well-balanced; it still offers something extraordinary and intriguing, without being too extreme. It also pairs well with Kendall’s fashion, in our opinion. The Freak X is priced at US$26,400 (approximately S$35,645).

Vacheron Constantin Historiques American 1921 White Gold

The Vacheron Constantin Historiques American 1921 is a well-loved model by collectors. Many appreciate the beautiful design, with that little bit of quirkiness with its 45-degree rotated dial.

The design is not done by accident, nor was it created in the name of being different. Dubbed the driver’s watch, the idea was to allow the user to tell time easily while his or her hand is on the steering wheel. Despite the slightly unusual looks, the Historiques American 1921 still retains its classy and sophisticated appearance.

Kendall is no stranger to Vacheron Constantin, as he was seen wearing the Harmony Monopusher Chronograph and Traditionnelle World Time previously – as identified by our friends at Time & Tide. The Historiques American 1921 should be a nice addition to his collection, especially with that little bit of quirkiness. Prices begin at S$43,600 for the 36.5mm variant.

Patek Philippe Calatrava Pilot Travel Time


We round up the selection with the brilliant Patek Philippe Calatrava Pilot Travel Time.

Since the Calatrava Pilot was launched in 2015, the timepiece has slowly grown on us over time. Not only does the watch look refreshing, it is also highly functional as well – all thanks to its nifty dual timezone complication. Of course, as with all Patek Philippe watches, the Calatrava Pilot also features all the goodies in terms of its impeccable finishing inside out.

The Calatrava Pilot is the perfect watch for an individual like Kendall. Its dual timezone function is extremely useful, and we can also safely say that the Calatrava Pilot is highly versatile – it can be paired easily with most attires. The 42mm Reference 5524G is priced at S$76,400, and this is surely a great wristwatch that should easily make it into his watch collection.

Concluding Thoughts

We hope that you have enjoyed reading this week’s article. We certainly had lots of fun writing this article and helping fictional personas to build their watch collection. This is even more so, given that Kendall appears to be quite a watch collector with a rather respectable collection.

The watches that we have selected today are watches that we think will suit Kendall’s casual look. They are also stylish and a tad different from the usual, which is what Kendall is gunning for these days. Of course, as with his dressing, he tend to go for the “stealth wealth” look in the recent seaons. This means that it should not be too gaudy or ostentatious (hence, no yellow or rose gold watches), yet it should look presentable and respectable. These six watches should do that job perfectly.

Finally, do let us know your thoughts on our selection, as well as your feedback on this new series. If there are any fictional TV characters or personas that you would like us to feature, please let us know as well. We will be more than happy to try and make it happen.


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