First Luxury Watch – How to Buy


First luxury watch - Rolex OP39

New to this are we? Heads up! Your first luxury watch purchase is not going to be your last. O.K., sure, it could be. You could die from shame after buying a Richard Mille. #aintgonnahappen. So let’s proceed to helpful hint one: don’t let the perfect be the enemy of the watch you buy. In other words . . .

Resist the urge to compare watches

I know that sounds counterintuitive. But once you get locked into the idea that one watch is “better” than another, once you start pursuing “the best watch” you can find/afford, you’ll never stop.

First luxury watch Sinn

There’s always going to be something “better” – a watch that’s newer, more exclusive, more collectible, more complicated, more magic feather than the watch you own.

Allow yourself to have lust in your heart for the alluring stranger. But make sure you spend time wanting the watches you already have, not just the ones you want.

Think of your first luxury watch as your first child. A timepiece that will always occupy a special place in your heart. You’ll love the following luxury watches the same, but differently.

Relieved from the burden of seeking perfection, your main job for acquiring luxury watch numero uno becomes simple: avoid buyer’s remorse.  That’s easily done if you . . .

Follow your heart not your head

I’m not saying blow out the budget. Did I mention you should have a budget? Have a budget. Stick to the budget. Then find a watch within the budget that speaks to you.

A watch that says hello, is it me you’re looking for? Am I the watch that you will always love to wear because you will always love me? Quick question: what do you love?


We live in a world where we’re free to love whatever luxury watch we want; mechanical or quartz, bling or button down. If you love a watch that claims to be a supercar on your wrist, drive on! If minimalism floats your boat, cast off! The world is your Oystersteel.

I’ve honed-in on different visual watch styles. That’s because I’m a shallow human being. What flicks your Bic?

First luxury watch - IWC Pilot

There’s style: case size, shape and material; dial font, color, layout and indices; strap material, color and closing system. Branding: national origin, heritage and perceived status. Technology: type of movement, functionality, accuracy, reliability, durability and luminescence. And other stuff.

I did say this was easy. It is.

Grand Seiko

Collect images of a dozen watches you like. Yes, a dozen. Make a list of three things all the timepieces have in common. What do you like about all of them, in order or importance?

That’s what you love in a watch. That’s what you need to have in your first watch. Once you know what your “thing” is, go search for three watches without your budget that meet your criteria. Then it’s time to . . .

Sleep on it

In Paradise by the Dashboard Lights, the singer tells his female friend (asking for lifelong devotion) to let him sleep on the proposal. He doesn’t and lives to regret it. Praying for the end of time, in fact. You know the drill: buy in haste, repent at leisure.

First luxury watch: OMEGA Aqua Terra

Besides, it’s literally true: your brain recalculates while you sleep. That freaking awesome watch that got stuck in your mind like 1 877 Kars 4 Kids (sorry, had to be done)? Gone in the morn.

If your pondering pissed away a chance to buy the watch you’d settled on, chillax. We’ve already established the fact that there will always be another horological bus coming down the road. If there wasn’t I’d have nothing to write about.

Howard pocket watch

And I’m right about this. When you’re finished with this process, go ahead and pull the trigger. Everything’s going to be alright.

If you see your first luxury watch in its proper perspective, if you know your heart’s horological desire, if you give yourself time to contemplate a potential temporal companion, you’ll end up buying a watch that will enjoy pride of place in your nascent collection.

As you gain experience, you will see flaws in your first purchase. But because you chose wisely, you’ll continue to appreciate what drew you to that luxury watch in the first place. Cherish is the word.


  1. ““once you start pursuing “the best watch” you can find/afford, you’ll never stop.”

    I’m looking forward to the Buyers Guide episode that demonstrates strategies to best minimize household blowback. Because let’s face it, sheltering (or at least mitigating) the true costs from a significant other is an important part of any growing hobby.

    I say that as someone who’s already neck-deep into analog photography and a certain German car brand with its engine in the rear. While we have a pretty good “Don’t ask, don’t tell” policy going on at the moment, I’m not sure diving into watch collecting is going to help my cause.

    • Any good hobby requires careful off-book transactions and a slush fund. My wife has no real idea of the cost of racing, and neither do I. I used to have a great slush fund from traveling within 100-200 miles for work by driving a 70mpg 2005 Honda Insight hybrid and collecting $0.59/mi in reimbursement. I could force my employer to issue as a separate check as well and it fell fully within the letter and spirit of expense guidelines. Had a bit more trouble concealing the cost of a professionally built roll cage, but she got herself a fancy spin bike for home (not from a publicly traded company) so we figured its best to just pretend we didn’t notice the other’s profligacy.

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