The World's Most Expensive Watches

March 5, 2008— -- Evan Zimmermann loves watches. He's so passionate about horology, in fact, that four years ago he quit his day job as a lawyer and became the managing director of New York's Antiquorum, the largest watch auction house in the world. Now, immersed in the world of watches, Zimmermann, 40, can keep an eager eye on rare timepieces as they become available to add to his constantly evolving personal collection.

"I used to represent the auction house as a lawyer," says Zimmermann. "But when I realized that I preferred to be around people talking watches at the Antiquorum offices than practicing law, I knew it was time to make the switch."

Zimmermann collects vintage Rolex sports models from the 1950s and '60s, which were among the first watches created for use in specific recreational pursuits. Classic and simple in style, the Rolex was considered the first truly waterproof, air-tight sport watch back in 1927 after Mercedes Gleitzes wore it during a 15-hour swim across the English Channel and it kept ticking.

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"Most collectors have a niche," explains Zimmermann. "Whether it's a specific brand or era, you have to narrow down your collection to have a truly focused search. Having too broad a criteria makes it too easy to find watches, and the whole excitement of collecting is in the hunt."

Zimmermann bought his first Rolex at an auction eight years ago. He paid $1,500 for a 1954 Rolex Submariner, made collectible because the word "Submariner" was written on the dial in red. Rolex later wrote the name only in white, making the red ones a rare find. Were he to sell it today, he anticipates it would fetch $15,000.

Nowadays he spends considerably more. His most recent acquisition was a Double Red Sea Dweller model 1665, bought at a Miami watch show for $20,000. This is one of three or four watches he plans to buy this year.

The joy of the chase--he once flew to Japan to inspect a watch at the airport, then caught the next flight home--is only part of the thrill. Unlike collectors of, say, rare coins, Zimmermann actually uses his collection on a daily basis. And when he gets it right, his hobby is a smart investment.