Buying Time

Tag Heuer
Monaco

First released in 1969 for the Monaco Grand Prix, it's credited for being the first automatic as well as the first square cased chronograph. Steve McQueen memorialized the watch in the 1971 film, Le Mans, and it's been legendary ever since.

$3,825 at Amazon

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  Alternative: Jazzmaster chronograph, $1,495 by Hamilton

IWC Portuguese Chronograph

One of IWC's signature pieces, its roots trace to the late 1930s, when two Portuguese businessmen were searching for an accurate wristwatch. It's had many variations since, but this elegant chronograph is among the most recognized.

$6,345 by JomaShop

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  Alternative: Automatic chronograph, $1,265 by Archimede

Omega
Speedmaster

Dubbed "The Moonwatch," this manual winding gem is one of the only timepieces qualified by NASA for space travel and has an impressive history. It was the first watch on the American spacewalk in the Gemini 4 mission and then was worn on the first walk on the moon for Apollo 11.

$4,800 at Amazon

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  Alternative: Swiss Army chrono classic, $862 by Victorinox

Rolex
Submariner

One of the most recognizable timepieces from the world's most popular watch company. The Sub was designed in the 1950s for diving and the design has remained virtually unchanged since then. Sean Connery wore one in 1962's Dr. No, and it went on to appear in eleven Bond movies.

$6,795 at JomaShop

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  Alternative: Automatic diver watch, $366 by Military Watch Co.

Patek Philippe
Calatrava

Patek Philippe is regarded as one of the finest and most prestigious watchmakers, and the Calatrava is the flagship model. Understated and minimal, the classically styled white gold watch fits "stealth wealth" to a tee.

$24,300 at JomaShop

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  Alternative: Automatic date watch, $595 by Tissot

Breitling
Navitimer

One of the most recognized aviation watches, its origin dates back to the 1940s when a slide rule with a logarithmic, double rotating slide rule scale was added to an already existing Breitling chronograph design.

$5,175 at Authentic Watches

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  Alternative: Rose gold chronograph, $310 by Orient

Jaeger-LeCoultre Reverso

Conceived in 1931 for British officers in India wishing to protect their precious timepieces during rough polo matches, the Reverso was designed so that at the flick of a finger, the delicate rectangular watch face would slide out of the watch case and back in with the metal side up, thus protecting the delicate crystal face from flying polo balls. Now, the watches often feature dual faces.

$8,528 at Prestige Time

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  Alternative: Evolution reversible, $450 by Rotary

Panerai
Luminor

With a history dating back to the 1860s, Officine Panerai supplied watches and equipment to the Royal Italian Navy. In the 1930s, they developed dive watches with a luminous material that was easy to read under water and in low light conditions. Panerai was exclusively used by the Italian military until the 1990s, when the watches were first offered to the public, ushering in the trend of larger timepieces.

$6,299 at Amazon

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  Alternative: Regattare 2011, $545 by Magrette

Audemars Piguet
Royal Oak

Named after a British Naval ship, the nautically designed Royal Oak was crafted in stainless steel and the octagonal case had the reinforcement screws exposed in order to mimic a diving helmet. This bold design was placed on to an impossibly slim case at the time—a mere seven millimeters—thanks to its ultra-thin movement, which still remains the thinnest today.

$13,520 at Prestige Time

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  Alternative: Wave chronograph, $1,405 by Ebel

Cartier
Tank

In 1917, Louis Cartier (grandson of the jeweler's founder) created an elegant watch inspired by the Renault tanks that were used on the Western Front in World War I. The thin, rectangular timepiece with a small sapphire cabochon embedded in its crown has become one of the most highly-coveted and copied watches of all time.

$8,200 at Tourneau

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  Alternative: Hampton automatic, $1,495 by Baume & Mercier

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