Forget The Insiders: The Only Rule Is To Wear What Matters To You
Over the weekend, The Wall Street Journal published an article, “Do Not Wear This Watch With a Suit! And Other Men’s Watch Rules to Know in 2025.” The article garnered significant attention, with many sending it in for our thoughts.
To be fair, many of the points in the article I agree with, including “Save the Apple Watch for the morning jog” and “Don’t overlook straps.” Others were harder to reconcile: “Avoid dive watches on Na to (straps).” But really, it’s the entire premise of the article that rubs me the wrong way. According to the author, the purpose of the article is to “help you avoid unintentionally committing a faux pas” and to elicit “quiet nods of approval from insiders.”
I will take the other side of the argument. There is no such thing as a watch faux pas; who cares what “insiders” think, and, most importantly, rules are meant to be broken.
Watch (Fashion) Media
Like any community, watch enthusiasts have coalesced around several big personalities (tastemakers) who set the norms and aspirational standards of success: a vintage Paul Newman Rolex Daytona poking out of a cashmere Loro Piana sweater while driving an air-cooled Porsche 911 to the country club with a chilled Negroni in the cup holder. For a normal guy, watch collecting can seem pretentious and unwelcoming.
When A King Breaks The Rules
King Frederik X of Denmark wore his Omega Seamaster Unit Watch when he acceded to the throne in 2024.
In January 2024, then-Danish Crown Prince Frederik X was proclaimed King of Denmark after his mother, Queen Margrethe II, abdicated the throne. His Majesty is no stranger to tool watches, as a member of the Frogmen Corps, he wore an issued Citizen Aqualand. When he became King, he chose his Omega Seamaster Unit Watch on a fabric strap, not a formal dress piece, but a tool watch tied to his service.
If there is one “watch rule” that is generally agreed on, it's that you don’t wear a dive watch on a fabric strap with formal wear, with many fashionistas saying you shouldn't wear a watch at all. The WSJ article puts it succinctly: “When suiting up, pick an understated ticker.”
Frederik X served with the Danish Frogman Corps, a maritime SOF unit, and wore an issued Citizen Aqualand.
Some from the watch community were quick to call out the “informal” watch/strap combo with comments like: “Dressing down shows disrespect for his office,” and “I'm surprised he did not wear baggy khaki shorts and a Hooters T-shirt to give the final touch to this casual moment.” (Credit: Hodinkee comments section)
Rolex Submariner 16800 on a W.O.E. Five Eye . . . In a tuxedo.
But again, taking the other side of the argument, this mindset implies that an individual is basing their watch decision on what someone else thinks. While I have never met His Majesty, I imagine he could wear any watch he wants on the most important day of his life, and he chose that one. This confidence to base your watch decision on what brings you personal satisfaction, and not to satisfy the opinions of others, is what makes it effortlessly cool.
W.O.E. The Fashionista
Despite having been profiled in Esquire (READ HERE), I am the last person in the world you should take fashion advice from. But I do believe your watch and clothing choices should be a personal expression of interest, not forced conformity to rules written by a suit in New York, London, or Los Angeles.
007 - The Rule Breaker
In Goldfinger (1964), Sean Connery famously wore a Rolex Submariner 6538 on what appears to be an undersized, striped nylon RAF-style strap. It wasn’t a perfectly fitted bracelet or fine leather band paired with a tuxedo; it was a humble fabric strap that looked almost improvised. The strap didn’t even fit properly, leaving spring bars exposed. Yet the image became one of the most iconic watch moments in cinema history.
That scene shows how irrelevant the rulebook can be. Bond embodies sophistication and elegance, yet one of his defining style moments came from breaking convention. Rather than diminishing the character, the crude strap amplified the aura of individuality and rule-breaking. If the world’s most famous fictional spy can pair a dive watch on a striped nylon strap with a tuxedo and make it iconic, then maybe we can all stop worrying about whether our watch will get a “quiet nod of approval” from the so-called insiders.
The Everyday Collector
And while kings and spies make for good headlines, the real spirit of collecting is found in the everyday guy. He’s the one who wears a scratched-up Seiko on a canvas strap to an important meeting because it’s the same watch he took overseas. Or the father who wears his beat-up Timex with a suit at his daughter’s wedding, because that watch has been with him through hard days and deserves a seat at the table. It’s not about curating aesthetics; it’s about wearing the watch that’s lived with you. That’s the part you can’t fake, and it’s why the so-called rules don’t apply.
“You shouldn't wear a leather strap with a dive watch” - a common “rule” from many watch elites.
Use Your Tools
At W.O.E., we say it often because it matters: Use Your Tools. Watches aren’t about rules, trends, or approval from tastemakers; they’re about living with an object that accompanies you through the highs and lows. A scratched crystal tells a better story than a polished Instagram shot. A fabric strap on a king or a spy says more about authenticity than any insider nod.
Whether you wear a G-Shock in the boardroom, a Submariner at a black-tie dinner, or your grandfather’s Omega while mowing the lawn, the point is that it’s yours. Break the rules, ignore the noise, and let the watch on your wrist tell your story.
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18 comments
Normally when I chose to wear something “daring” for myself, which may constitute “a break of rules”, the collectors I want to get in touch with, will appear exactly because of that. I/we want to know your story, where this watch/style comes from and what it means to YOU not to some polished magazines. use your tools. not those someone else tells you to. real recognize real.
What is style and how does it evolve? There is the norm and then someone breaks out, leads with something new and that then has a gaggle of followers to reset the status quo. In that sense, celebs, characters, military leaders, public figures or your dad- do something with their reasons to wear a watch or anything, and others follow. There are no rules as long as someone can justify that watch combo or choice. The only rule might be that you cannot do something absurd without any thought. If you have a reason- it could become a trendsetter.
Some of us are active in a way the makes dresswatches go bad fast, I rather use a nice divewatch that last all of the time and do not care about being fashionable.
Amen. Thanks for calling out pretentious BS.
“….It’s a little bit on the nose.” WTF does that even mean? If someone used that phrase in conversation I’d either laugh or walk away.
The most sage advice in this piece is: “This confidence to base your watch decision on what brings you personal satisfaction, and not to satisfy the opinions of others, is what makes it effortlessly cool.”
I was fortunate to be interviewed for the Esquire piece linked in the article. (I agreed to do so after notifying WoE.) The Esquire piece is a nice homage to the personality behind the website. My only quibble with it is a typo in the model name of my cherished Breitling. It should have said “Breitling Avenger Blackbird 48.”
Thanks for keeping us informed and on track!