The 3-Watch Collection Every Executive Should Own (And Why)
What 50 serious collectors told me when I asked: “If you could only keep three watches, which would they be?”
I've had this conversation dozens of times. An executive walks into a meeting wearing five different watches over five days. None of them work together. None of them serve a clear purpose. It's watch collecting as accumulation—not strategy.
Then I ask the question that changes everything: "If you could only keep three watches, which would survive?"
The answers are remarkably consistent. Across 50+ conversations with serious collectors—private equity partners, attorneys, surgeons, founders—80% arrive at the same framework:
One watch you wear six days a week.
One watch that makes a statement when you need it.
One watch for the occasions that matter.
Daily driver. Statement piece. Occasion watch.
That's it. Three watches. Three distinct purposes. Zero overlap.
And here's what surprised me: The collectors with 15+ watches and the collectors with exactly three watches gave me the same answer. The difference? The three-watch collectors stopped buying once they had the framework covered. The 15-watch collectors kept going—but still wore the same three watches 90% of the time.
This isn't about budget constraints. This is about understanding that a well-built three-watch collection solves 100% of real-world scenarios while a poorly-planned ten-watch collection solves maybe 60%.
Let me show you how to build the collection that actually works.
Watch #1: The daily driver (the watch you stop thinking about)
Purpose: This is your default. The watch you wear to the office, on weekends, traveling, working out if you're brave. It needs to be comfortable enough to forget you're wearing it and versatile enough to work with 90% of your wardrobe.
The criteria:
Durability: You're not babying this watch. It needs to handle daily wear without stress.
Versatility: Works with a suit and works with jeans. Formal enough for client meetings, casual enough for Saturday errands.
Comfort: If you're adjusting the bracelet or noticing the weight, it's the wrong watch.
Water resistance: At least 100m. You shouldn't have to remove it to wash your hands.
Legibility: You should be able to read the time instantly in any lighting.
What serious collectors actually wear:
The most common answer I hear? Rolex Submariner. Not because it's the "best" watch. Because it's the watch that disappears. Steel case. Black dial. Oyster bracelet. Works with everything. Survives everything. Current market: $13,500-$14,500 pre-owned.
But here's the thing about the Submariner: it's become a statement by default. Everyone knows what it is. Everyone knows what it costs. For some executives, that's perfect. For others, it's too much watch.
Alternative daily drivers that work just as well:
Omega Speedmaster Professional ($6,200-$7,100 pre-owned): The Moonwatch. Steel case, black dial, incredible heritage. Less "look at me" than the Submariner. Chronograph actually useful. Works on leather or bracelet. This is the watch that NASA chose for a reason—it's bulletproof.
Cartier Santos Large ($6,500-$7,500 pre-owned): The first pilot's watch (1904). Square case. Integrated bracelet. Somehow works as both a sport watch and dress watch. More refined than the Submariner, less common, but just as versatile. QuickSwitch strap system means you can go from steel bracelet to leather in ten seconds.
Rolex Explorer 124270 ($9,000-$10,000 pre-owned): The anti-Submariner. 36mm. No date. No complications. Just time. Flies under the radar but insiders know. This is the watch for executives who don't need to announce anything.
The decision:
Your daily driver should be the watch you reach for without thinking. If you're deciding between two watches every morning, you don't have a daily driver—you have two watches competing for the same role.
Watch #2: The statement piece (the watch you wear when it matters)
Purpose: This is the watch for the moments that count. The pitch. The negotiation. The celebration. The event where you want your watch to do some of the talking for you. Not loudly—but intentionally.
The criteria:
Presence: This watch should be noticed by people who notice watches—and nobody else.
Material: Precious metal preferred. Steel can work, but gold/platinum signals differently.
Recognizability: People in your industry should know what this is.
Rarity: Not everyone in the room should be wearing one.
What serious collectors actually wear:
The most common answer? Rolex Day-Date. The "President." Yellow gold, champagne dial, President bracelet. This is the watch for people who've made it and don't need to explain. Current market: $35,000-$42,000 pre-owned depending on age and dial.
Warren Buffett wears one. It's the watch you wear to close the deal, not to pitch it.
But the Day-Date isn't the only answer—and for many executives, it's not the right answer.
Alternative statement pieces that work:
Audemars Piguet Royal Oak ($25,000-$35,000 pre-owned for steel, $45,000+ for gold): Gerald Genta's masterpiece. The luxury sports watch that changed everything. Octagonal bezel. Integrated bracelet. Instantly recognizable. This is the watch for executives in finance and tech who want to signal "I know what matters."
Patek Philippe Calatrava ($18,000-$25,000 pre-owned): The anti-Royal Oak. Small. Thin. Elegant. No complications beyond time and date. This is the dress watch that serious collectors respect. Understated in the best way. The watch for attorneys and private equity partners who prefer quiet signals.
Omega Seamaster Aqua Terra ($4,500-$5,500 pre-owned): The accessible statement piece. Not as expensive as the others, but beautifully finished. Vertical teak dial. Master Chronometer certified. This is the watch that says "I care about quality, not status." Works for younger executives or industries where a $40K Day-Date would be tone-deaf.
The decision:
Your statement piece should feel like an occasion when you put it on. If you're wearing it three times a week, it's not a statement piece—it's become your daily driver. This watch should live in the box most days and come out when it counts.
Watch #3: The occasion watch (the watch for black tie and board meetings)
Purpose: This is the watch for formal events. Weddings. Galas. Board presentations. Retirement dinners. Anywhere a sport watch would feel wrong. This watch should be thin, elegant, and forgettable in the best possible way.
The criteria:
Thinness: Must fit under a dress shirt cuff without catching.
Simplicity: Time only, or time and date. No chronographs. No dive bezels.
Dial: White, cream, or champagne. Dark dials work but light dials are more traditional.
Case size: 36-40mm. Anything larger looks wrong with formal wear.
Leather strap: Bracelet works for business formal. Leather works for black tie.
What serious collectors actually wear:
Here's where the answers get interesting. Because the "occasion watch" isn't about brand recognition—it's about not being wrong.
The most common recommendations:
Cartier Tank ($3,500-$6,000 pre-owned depending on size/material): The rectangular dress watch that's been right since 1917. Thin. Elegant. Works with everything from a tuxedo to a gray suit. Available in steel, gold, or two-tone. This is the watch your grandfather should have left you.
Jaeger-LeCoultre Master Ultra Thin ($6,000-$8,000 pre-owned): As thin as luxury gets. 39mm case, under 9mm thick. Automatic movement. Sector dial option for vintage appeal. This is the watch for collectors who want something beyond the usual suspects.
Omega De Ville Prestige ($2,500-$3,500 pre-owned): The value play in dress watches. Small seconds. Steel case. Simple dial. Co-Axial movement. Not flashy. Not expensive. Just right for formal occasions where you need a watch but don't want it to be the conversation.
Rolex Datejust 36mm ($8,000-$11,000 pre-owned): The crossover watch. Works as a daily driver for some, works as a dress watch for others. Fluted bezel adds formality. Jubilee bracelet dresses it up. White or champagne dial keeps it elegant. This is the one watch that could arguably fill two roles—but only if you keep it conservative.
The decision:
Your occasion watch should be the one you wear the least—but appreciate the most. It's the watch that makes you adjust your cuffs differently. The watch that reminds you that some moments deserve formality.
How to actually build this collection (without making expensive mistakes)
Now that you understand the framework, here's how to execute:
Step 1: Start with the daily driver
Don't buy anything else until you've worn your daily driver for three months straight. If you're reaching for a different watch on day 15, you chose wrong. The daily driver test is simple: do you forget you're wearing it?
Step 2: Wait six months before buying the statement piece
Once your daily driver is locked, give yourself time. The statement piece is expensive and needs to be right. Wear your daily driver to the events where you'd wear the statement piece. Notice what other people wear. Notice what you wish you were wearing.
Then buy it.
Step 3: The occasion watch can wait a year
Unless you're attending formal events monthly, you don't need this watch immediately. And honestly? Your daily driver can cover formal events for a while. The occasion watch is the last piece—and the easiest to get wrong if you rush it.
The trade-in strategy:
Here's what smart collectors do: They trade up within categories, not across them.
You don't trade your daily driver for a statement piece. You trade your Submariner for an Explorer. You trade your Steel Daytona for a gold Day-Date. You stay within the role and upgrade the execution.
At Royalty Timepieces, we see this constantly. A client buys a Speedmaster as his daily driver. Wears it for two years. Decides he wants the Seamaster instead. We take the Speedmaster on trade. He applies that value to the Seamaster. His collection improves without expanding.
That's the difference between collecting and accumulating.
The three-watch collection that actually worked
Let me tell you about a client who got this exactly right.
He's a private equity partner. Makes eight figures. Could afford any watch. Came to me with seven watches and wore three of them.
I asked him the question: "If you could only keep three, which survive?"
He knew immediately:
Daily driver: Rolex Submariner (wears it six days a week)
Statement piece: Audemars Piguet Royal Oak in steel (wears it to pitches and closings)
Occasion watch: Cartier Tank in gold (wears it to weddings and galas)
The other four watches? He didn't remember the last time he'd worn two of them.
We consigned all four. He used the proceeds to upgrade his Submariner to a newer reference with better condition. Kept the framework. Improved the execution.
Two years later, he still has three watches. Still wears them in the same rotation. Still hasn't bought a fourth.
Because the framework works.
Bottom line
You don't need ten watches. You don't need five watches. You need three watches that serve three distinct purposes—and you need to actually wear them.
Daily driver: The watch you stop thinking about.
Statement piece: The watch you wear when it matters.
Occasion watch: The watch for moments that deserve formality.
Everything else is collecting for collecting's sake. Which is fine—if that's what you want. But if you want a collection that actually works? That covers every situation without decision fatigue?
Three watches. That's the number.
The question isn't how many watches you need. The question is: which three survive when you're forced to choose?
Build Your Collection Strategically. We'll Help You Get There.
At Royalty Timepieces, we work with executives and collectors to build watch collections that actually work—not just accumulate.
How we help:
Collection strategy consultation - We help you identify which roles you need filled and which watches fit your lifestyle
Trade-in program - Upgrade within categories without expanding your collection unnecessarily
Authenticated inventory - Every watch inspected by our in-house watchmaker, 100% authenticity guaranteed
Private sourcing - If we don't have the specific watch you need for your collection, we'll find it (typically 2-4 weeks)
Whether you're building from scratch or refining what you have:
Call us: 201-701-3421
Email: info@royaltytimepieces.com
Browse our collection: royaltytimepieces.com
The best collections aren't the biggest. They're the most intentional.
Let's build yours.
Royalty Timepieces | The Royal Standard in Horology
201-701-3421 | info@royaltytimepieces.com | royaltytimepieces.com
Royalty Timepieces is an independent watch dealer and is not sponsored by, associated with, or affiliated with Rolex S.A., Omega S.A., Cartier S.A., or any watch brand manufacturer. All trademarks are property of their respective owners.