Ben Clymer's fascination with watches started at 16 when his grandfather gave him an Omega Speedmaster right off his wrist. He's since channeled that enthusiasm into the respected and fast-growing watch blog Hodinkee and is now the go-to curator for brands looking to add some vintage watches into their retail mix. We asked Clymer about entering the world of vintage watches ...

Ben's favorite vintage pieces in his collection: 1957 Omega Ranchero and a 70's Heuer Camaro

What's the first step when buying vintage?

Only buy a watch you really love. If you look at it and aren't totally infatuated, it's not worth your money. Buy something you're going to wear and love every second of. Too many guys buy watches because their friends or co-workers tell them they're cool, but if you don't love it yourself, what's the point?

What are some things we should be looking for?

You want to do your research. There are too many good fakes out there—entire factories in Asia that produce fakes—and if you buy one, your $15,000 investment can become a major loss if you try to sell it. Talk to someone you trust and don't be afraid to get a second opinion. If the dealer has nothing to hide, he'll happily let you show it around.

What are some warning signs of a fake?

If the crown isn't signed, that's a quick indication that something's been toyed with. Also, look at the color of the markers, if they're perfectly white or glow in the dark, and the watch is 50 years old, that doesn't compute. Use common sense—if a dial looks brand new, it probably is.

Any vintage recommendations?

If you're ready to make the leap, you can't go wrong with the Rolex Submariner Reference 5513, an Omega Speedmaster Caliber .321, which was the real moon watch, or a Heuer Carrera 2447s (shown left).