The best vintage watches on the market

From divers to dress watches, we asked the experts what you should be looking out for when considering an older model for your next timepiece

The past decade has seen a massive resurgence in the popularity of vintage watches. In just the last two years alone, the record for the most expensive watch sold at auction has been smashed twice — first with a steel Patek Philippe 1518 and then with the Rolex ‘Paul Newman’ Daytona. The pre-owned watch market is now reportedly worth an astonishing $5 billion annually, according to Swiss research company Kepler Cheureux. That’s the same as the GDP of the Bahamas.

Adding a few vintage watches to your collection can be a smart investment. But it’s one that can carry some emotional weight, too — a great deal of collectors are now buying models from their birth year, for example, or those of their loved ones.

"The Vintage Watch market has exploded over the last year with record prices achieved at auction..."

With a dizzying amount of options out there, we sat down with a couple of experts in the big categories of vintage horology, and asked them to take us through the options.

David Silverman runs the Vintage Watch Company — one of the top retailers in the Burlington Arcade and a Rolex specialist. Jon Bues, meanwhile, is a Senior Editor at Hodinkee and a well-known figure in the world of watch writing.

Whether you’re buying a vintage timepiece as an investment or for purely aesthetic reasons, here is our experts’ selection of the best watches that you can pick up either at auction, at a private sale or from a trusted watch dealer.

The Investment

Some will say that you should only ever buy a watch if you plan on wearing it, enjoying it and living with it. But investing in high-end wristwear has proven very lucrative in recent years.

The best vintage watches on the market
Credit: The Vintage Watch Company

If you are going to invest in a vintage watch, Bues suggests early Rolex sport models. “Rolex sports models have a well-earned reputation for doing well over time,” he says. “Of these, I would say that early Explorers probably represent the best current buying opportunities — they certainly sit well below the high prices seen for early Submariners and Daytonas.”

(Of course, it was a Rolex Daytona that broke auction records for the most expensive watch in history when Paul Newman’s old model — with the inscription “Drive Carefully, Me” on the back — sold for over $17 million in November 2017.)

The Diver

The thought of plunging underwater in an expensive Swiss watch might cause some of you to break out in cold sweats, but original dive watches from the 1950s are things of utilitarian beauty. In fact, many of them haven’t changed in design in over 60 years.

The best vintage watches on the market
Credit: The Vintage Watch Company

If you want the original diver’s model then Silverman says the so called ‘Big Crown’ Submariner is the only way to go. “The Rolex Submariner is the original diver’s watch,” he tells us. “It was created in 1953 with a depth rating of 100m and famously fashioned by Sean Connery in the first James Bond movie Dr. No in 1962. This piece, known to collectors as the ‘Big Crown’ owing to its larger than normal Winding Crown, reached a depth of 200m.”

The Dress

Dress watches can come in all shapes and sizes and are often the measure of a man’s class and status. But the ultimate way to show your prestige is a dress watch that predates you.

The best vintage watches on the market
Credit: Chrono24

If you want one that won’t break the bank but will amaze on the wrist, Bues recommends the IWC Caliber 89. “Consider mid-century gold dress watches from brands such as Audemars Piguet and IWC,” he says. “These remain great bastions of value. The quality that these brands are known for today is on display. The IWC Caliber 89 is a wonderfully proportioned dress watch with a workhorse movement. A very nice gold example will set you back about $3,000.”

The Sports

The Quartz Crisis was a turbulent time in watch history that threatened to end it all. When the first quartz (battery powered) movements were introduced and threatened to topple the entire industry in one hacking movement. The saga changed everything for Swiss watches — but it also created some of the best designed sports watches we’ve ever seen in the process.

The best vintage watches on the market
Credit: Chrono24

Bues recommends one of these classic 1970s designs. “In the midst of the Quartz Crisis of the 1970s, the modern ‘sports luxury’ watch was born,” he says. “This is when we saw the first Audemars Piguet Royal Oak [1972], the first Patek Philippe Nautilus [1976], and the Vacheron Constantin 222 [1977]. Great early examples of these fantastic vintage steel sports watches are the dream for many collectors.”

The Pilot’s

Watches have been taking to the skies ever since Alberto Santos-Dumont first took off in 1906 with a specially-made Cartier strapped to his wrist, and the amount of vintage pilot’s watches on the market is staggering.

The best vintage watches on the market
Credit: Chrono24

Taking this tradition to new heights, the Breguet Type XX is the one aeronautical watch that Bues would opt for. “There are more than a few classics here,” he tells us. “The Breguet Type XX is very appealing watch with a wonderful history.”

The time and date

Silverman points out how “Rolex were at the forefront of creating the aperture on the watch face to display the date. The first Datejust model appears in 1945 and is a huge success.”

The best vintage watches on the market
Credit: The Vintage Watch Company

Bues is equally passionate about the model’s investment potential. “The Rolex Datejust is a classic for a reason,” he says. “This is great entry-point into watch collecting. Nice examples are readily available and relatively inexpensive.”

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Further Reading