I’ll always remember the one that got away. A decade ago my wife and I were in Mexico City staying in a cheap hotel. She was immensely pregnant and I had plenty of time to walk around the city while she napped. One afternoon I wandered for a good hour and came upon a little watch shop inside of what looked like a newspaper stand. It was full of amazing watches—from inexpensive Omegas to amazing old Rolexes. I was in heaven.

And then, suddenly, there it was: an original Omega Speedmaster, black and white, priced far below anything I expected. I fondled it. I ogled it. I was going to buy it.

But I didn’t want to pull the trigger just then. I looked around quickly, made a note of the address, and went back to the hotel.

The next day we both wandered through the streets of Mexico City trying to find the little watch shop in the newspaper stand. It was gone, a Brigadoon of timepieces. The Speedmaster I had loved, had dreamt about, had coveted, disappeared.

I swore I’d never let a watch escape me again. And here’s how to make sure such a fate never befalls you, either.

You can get up to 50 percent off any watch with a little digging. Watches are marked up nearly 100 percent in some cases and if you find the right dealer you can work them down from the MSRP.

Starters
A watch makes the man. Wearing a good watch can brighten your mood, improve your confidence and show you have joined a fraternity of men who appreciate engineering, artistry and ambition.

But what should you buy? Buy a watch that you love. If it costs a lot of money, then save up. If it’s cheap then buy it and resell it when you’re tired of it. Really like a Rolex you saw in a Dubai duty free? Run the numbers, check online for deals and buy it if you have the dosh. I’ve lost so many watches in so many amazing places simply because I vacillated for a day too long.

Also, ask for a discount. Watch resellers know they have expensive things and they’d like to move some inventory. Push for a deal and you’ll probably get it.

Sources
Authorized dealers are a good place to start, especially if you have expensive tastes. Finding a dedicated watch hunter is a real treat and once you get more deeply into watches they will be invaluable.

You can also hit a site like Crown & Caliber. These guys list thousands of pre-owned pieces in excellent condition. Just don’t buy on eBay and watch out for forums—people can be trustworthy there, but until you really get to know them it’s a crapshoot.

The Omega Speedmaster Original is the definitive chronograph. The first watch on the moon, the Speedmaster should be in every watch fan’s arsenal, at least for a little while.

Negotiating
You can get up to 50 percent off any watch with a little digging. Watches are marked up nearly 100 percent in some cases—fashion watches like Burberry and Fossil are ridiculously overpriced—and if you find the right dealer you can work them down from the MSRP. If that doesn’t work, buy used.

Don’t expect your watch to appreciate in value. This isn’t Antiques Roadshow. Rolex and Patek Phillipe can usually be sold for about as much as you paid for them but unless your watch is 100 years old or was worn by Marilyn Monroe on her deathbed, you’re not getting much of a return there.

Buyin’ Time
What follows is a rundown of watches for every budget and stage in life. If you’re older than 30 don’t bother with the low-end. If you’re just starting out and heading into your first job, any old watch will do. The one no-no? Don’t wear a cheap running watch with a suit. That look only works for presidents who need to pretend they don’t make millions of dollars, so they strap on a Timex Ironman in public while wearing a Rolex at home.

If you spend more than $8,000 on a three-handed watch—a watch with just an hour hand, minute hand and second hand—then you were had (see: Rolex).

Low End
Who’s it for? Baby’s first job interview.
Brands: Christopher Ward, MVMT, “fashion” watches.
Breakdown: You’re fresh out of school. You bought a suit. Time to accessorize! Your first watch should cost somewhere between $95 and $200 and it really doesn’t matter what you buy—just make sure it looks good. Like jewelry from H&M, a cheap watch is a cheap watch. There is literally no difference between cheaper watches, be it from online darling MVMT or Michael Kors. How do you identify a cheap watch? It has a quartz movement. Quartz is the equivalent of a cubic zirconia in a pinkie ring: it looks OK but you’re not fooling anyone.
What to buy: The Seiko Orange Monster. This low-cost dive watch is the definitive entry-level piece. It has a mechanical movement, great styling, and it comes in multiple styles. You can’t go wrong with this one. Looking for something more formal? Look at the Tissot Le Locle or a Swatch Sistem 51. They are great and look far more formal than you’d expect.

seiko-orange

Mid Level
Who’s it for? Career builders, guys who appreciate engineering.
Brands: Omega, Tissot, Breitling, Bell & Ross, Tudor.
Breakdown: At this level you could be paying as much as $8,000 for a watch. If that seems like a lot then you probably picked the wrong hobby. These are great watches made by hand and can really make your suit or jeans pop. A good watch defines a dude and brands like Omega and Breitling know it. There’s not much glamor here but anyone who knows a minimum about watches will know that you have something special. These are gateway drugs to more expensive pieces, so beware. One trick? Buy, wear and trade. Join forums and real watch blogs to meet other likeminded watch nuts and save a lot of money by flipping your pieces once a year or so. It’s fun and makes a lot of sense.
What to buy: The Omega Speedmaster Original. This is the definitive chronograph. The first watch on the moon, the Speedmaster should be in every watch fan’s arsenal, at least for a little while.

omega-speedmaster

Mid High End
Who’s it for? A business dude, guys who don’t spend money on cars (or really like cars and have some money left over).
Brands: FP Journe, Rolex, Panerai, Audemars Piguet, Panerai.
Breakdown: Once you enter the rarified air of mid-high end—and $10,000 to $100,000 is mid high end—things start getting interesting. Your mission in this space is to look for complications (features) on your watch that you can’t usually get. Think chronographs (stopwatches), multi-time zones, moon phase indicators, and sometimes even chimes. If you spend more than $8,000 on a three-handed watch—a watch with just an hour hand, minute hand and second hand—then you were had (see: Rolex). At this point you probably know what you want and you know where to get it. You’re an established collector and, while there’s no accounting for taste, you can’t go wrong making an executive decision on a nice piece.
What to buy: The Breguet Type XX. This is an “affordable” piece of watchmaking art. Designed for early transatlantic pilots the Type XX is beautiful, well made and comes from one of the most venerated houses in watchmaking. I like the brand so much I wrote a book about it.

breguet type xx

You Paid What? Tier
Who’s it for? God knows.
Brands: MB&F, Patek Philippe, watches with a lot of gold and diamonds.
Breakdown: Watches can get obscenely expensive for a couple reasons. First, they can be covered in pave diamonds and contain a sliver of unicorn horn for potency. Or they can be handmade from scratch by some sort of legendary figure or madman. Either way, expect to pay over $100,000. Why? Imagine you’re buying a car and you hit the dealership. You can get a mass-produced Toyota that drives well or they offer you a handmade Toyota—basically the same car— but someone handcrafted in his backyard. He mined the metal, smelted it, poured the glass for the windshield and hand-polished the engine with a toothpick for two years. Sure both Toyotas are basically the same—don’t tell the real watch fans I told you this—but the handmade one has a lot more cachet… if you’re into that sort of thing. Expensive watches are also expensive for the sake of being expensive. It’s a glamour thing. Bottom line? It’s a crazy industry.

Watches are important, they’re beautiful, and a good mechanical will hold you in good stead until you die. Choose wisely and you’ll be happy forever. Choose poorly and you’ll spend a day wandering Mexico City in search of the treasured timepiece that got away…

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