Question: I am currently a freshman in college and I'm looking to buy my first vintage watch. Omega and Rolex interest me, but at my budget of $2000-$2500 there are so many watches to choose from that I can't differentiate what's worth the money and what's not. What are some good options for what I'm willing to spend? Thank you.
Answer: Turner, great question. Before I go over some excellent wristwatches that best fit your ideal price range, I'd like to briefly share something with you.
Go back three and a half years and this is probably what I would've said to you if you asked me about Rolex's Submariner and Omega's Speedmaster: The Submariner is a time-only Rolex, originally intended to be worn by divers, and is widely-known for its appearance in eleven James Bond films. The Speedmaster is a classic Omega chronograph that earned a cult status after passing a series of NASA's intense qualification tests, sent on the first manned mission to the moon, and returning to earth intact. Pretty straightforward, right? But when it came down to recognizing the historical changes and continuities of each watch, I was clueless. To further, and more clearly, explain my point using that Sub VS Speedy comparison, I couldn't recognize the differences between a 1680 Sub and a 16800 transitional Sub or a 105.002 Speedmaster and 105.003 Speedmaster. But in time, I learned. So don't worry about not knowing all the little details at first. All you have to know for now is, like you said, "what's worth the money and what's not."
Now, let's get down to the good stuff.
The Rolex Datejust
The most iconic, no-frills wristwatch ever produced by Rolex is the Datejust. Aside from knowing some Datejust owners who are quite important collectors, I happen to be the proud owner of an awesome slate-blue dial 1603. I would eagerly advise you to make a Datejust your first vintage watch, not only because it is great looking, but because one in good condition, from a relatively early year, will hold its value well. Definitely check out Datejusts with linen or pie-pan dials, unusual bezels, and riveted oyster or oval-link jubilee bracelets.
The Omega Seamaster
Omega's Seamaster represents a superior caliber of Swiss watchmaking at an entry-level price. You can get your hands on a basic Seamaster for anything from $200 to $2,000. At your price point, I'd recommend a solid gold 50's, 60's, or 70's Seamaster on a beads of rice bracelet. If you can find a full set (box+papers) steel Seamaster for under $1,250, I'd say go for it!
By the way, the Seamaster was also my first vintage watch:)
The Omega Speedmaster
At the top of your price range would be the Speedmaster. I do have to admit, this rivals the Datejust's coolness, but acquiring one is a challenge. Your best bet (when spending 2k-2.5k) for a true Speedy (moon watch or pre-moon) is eBay, unless you prefer something like what is shown in the photo above.
Good luck and enjoy your search for that first vintage watch!