First let me say that I am definitely biased: My first Rolex was an old reference 1675 GMT-Master from the late 1960s that I won on eBay before I knew anything about vintage watches in general or Rolex history in specific. But I was lucky because the watch turned out to be both A) genuine and B) a totally awesome choice for a noobe. Here’s what it looked like…

And here’s why it’s a great choice for the guy who just got his first really good payday or bonus: 

1. It’s one of the archetypal Rolex “Tool” watches: tough, water resistant (to a degree–have it pressure tested before you dive the Barrier Reef) and extremely practical–there’s a date and a second timezone complication.  You read your secondary timezone by rotating the bezel and matching its 24-hour calibration with the fixed 24-hour hand. By rotating it to the right, you are reading earlier timezones in the west; by rotating to the left, you’re reading later timezones in the east. If you’re a traveller and want to know what time it is at home, this is the watch for you. There’s a reason why the GMT-Master was (and still is in its current incarnation) the choice for pilots and ships’ captains.
2. It makes a statement on the wrist while still maintaing a relatively low profile. The GMT-Master is relatively large at 40mm across but thinner than a Submariner of the same era and sits quite flush against the wrist. So it can fit nicely beneath a dress shirt if needed but also looks just as good with jeans and a T-shirt. By today’s less formal fashion standards, you can pretty much wear a GMT-Master on any occasion and it’ll put you in a good light.
3. The watch is expensive but holding its value, meaning that if you need to cash out of it one day you can most likely recoup all or most of what you bought it for. After a major surge between around 2004-8, the vintage Rolex bubble burst to a degree and prices came back down a bit. But the common matte dial reference 1675 GMT-Master (as pictured) has been holding steady at around $4500 USD give or take for the last couple of years and that seems to be its level (it might even be sneaking up again a bit of late). Obviously, condition is king, so buy the best example you can with a nice fat case & lugs and near-flawless original dial (important!). But if you’re selective and patient and buy a nice example, there’s no reason to fear that you have thrown your money out the window on a vanity purchase. You’ve merely parked that $4500 some odd dollars on your wrist. And doesn’t it look a heckuva lot better there than earning bupkis in your savings account?

Specs: 40mm diameter, stainless steel, automatic self-winding movement (Perpetual), screwdown caseback & crown (Oyster), acrylic crystal, rotating dual timezone bezel calibrated to 24-hour time, fixed 24-hour GMT hand, water resistant, date with instantaneous date change at midnight, Chronometer.

Further reading in greater detail: Check out this old article of mine, Evolution of the GMT, over at Doubleredseadweller.com, an excellent resource for the Rolex Sports watch enthusiast.

Some more images for your enjoyment and edification, including under the hood:

And the best and safest place to buy your GMT-Master or any other vintage Rolex is over at Vintage Rolex Forum’s Vintage Market.