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Buying Time

Even amidst the smartphones and tablets, there's been something of a wristwatch renaissance lately. We're not talking about the digital LED sport watches or fitness bands you see on athletes, but the ticking timepieces that now grace the wrists of discerning men of all ages. The most sought after styles are still made by companies whose history is long, designs are timeless and products have revolutionized the horological world. These heirloom grade pieces are the flagships of their respective makers—recognized by aficionados and laymen alike. The watches, worn by celebrities, icons and revolutionaries, existed before us and will certainly endure once we're gone. What's more, if you're blessed enough to own such a watch, it's an investment you'll be able to pass onto your kids. Of course, just because you can't afford to procure such a beauty right now, doesn't mean you should settle for anything less than quality. Herewith, ten iconic timepieces along with some more attainable alternatives from respectable makers that still boast impressive features like chronographs and mechanical movements.


Tag Heuer

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

    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

    Alternative: Automatic chronograph, $1,265 by Archimede


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

    Alternative: Swiss Army chrono classic, $862 by Victorinox


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


Patek Philippe

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

    Alternative: Automatic date watch, $595 by Tissot


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

    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

    Alternative: Evolution reversible, $450 by Rotary


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

    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

    Alternative: Wave chronograph, $1,405 by Ebel


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


Another way to score an iconic watch for less? Buy vintage. We asked Hodinkee's Ben Clymer about what to look for when shopping for a pre-owned timepiece.