2016 will mark the 100th anniversary of America’s love affair with the wrist watch. In 1916, The New York Times officially declared that the – and we quote – “silly-ass fad” that Europeans had pioneered was starting to be welcomed stateside.

The modern wristwatch tradition began in the trenches. There had been some occasional examples of the technology before, but as military sophistication intensified in the early 20th century, keeping time became essential for soldiers to accurately relay information. And since fiddling for a pocket watch under fire wasn't exactly practical, the watch as we know it started . But the invention has gone far beyond those utilitarian roots – no matter the silly-ass fads of the day or decade, the watch has stood the test of time as an unmistakable mark of style.

And there are a few iconic pieces that have made an especially big mark. Some of the best-dressed, most effortlessly cool guys in the past century have worn beautiful examples of finely tuned watchmaking expertise, turning them into timeless signifiers of style.

Sammy Davis Jr.

Cartier Pasha

The Rat Pack crooner had a penchant for slick suits and bold jewelry, both of which he pulled off with an easy charm. For his wrist, he favored Cartier, the watchmaker that literally invented the first wristwatch in 1911, and whose masterpieces have adorned the wrists of countless icons since.

Sammy's was a flashy gold version, which he was gifted – complete with custom “I LUV YA” engraving – by none other than Frank Sinatra. The modern version has a slightly sleeker casing but preserves just enough flash to do Sammy proud. Message from Ol’ Blue Eyes not included.

Robert Redford

Rolex Submariner

A favorite of the one and only Sundance Kid, the Submariner is perhaps the perfect marriage of form and function. Originally designed as a divers’ watch (hence the name), the timepiece was originally created in 1953 as a piece of specialty sports equipment, and has since shot to popularity on the wrists of well-dressed guys with deep pockets. It's one of those iconic designs that you can recognize a mile away, and instantly invokes waves of envy.

Redford is an especially big fan, apparently, as he sported one in several of his legendary '70s movies like The Candidate, Three Days Of The Condor, and All The President's Men. The modern version is every bit as tough and elegant as it was back then – it still measures decompression stops for all your diving needs, and works just as well with a tux as it does 300 meters below the surface.

James Bond

Omega Seamaster

There's no style authority higher than Bond. And ok, we might be bending the rules slightly given that he's not a real person, but the character's taste in suits, cars, and watches has undoubtedly help set the standard of what modern day men aspire to.

The spy's choice of timekeeper has varied in the time between Connery and Craig, but Bond has exclusively worn the Omega Seamaster since Brosnan stepped into the iconic character's shoes. It's similar in both form and function to the (arguably more recognizable) Rolex Submariner, but this is the original – Omega has been making them since '48, five years before the Submariner made its debut.

Bond has been known to rock his watch on a nylon strap, though ironically, not the black-and-grey striped one that's earned the nickname "Bond NATO" among watch collectors. Connery's nylon strap had navy, olive, and burgundy stripes, and actually predated the modern-day NATO strap by eight years. In Spectre, though, Craig lends credence to the black-and-grey strap by wearing his Seamaster on an official Omega version of the NATO band.

An off-the-shelf version might not come with lasers or explosives like Bond's, but it will certainly increase your cool factor.

Steve McQueen

Tag Huer Monaco

The Monaco first appeared as a commemorative piece for the Monaco Grand Prix in 1969, capturing all the elegant glamor of its namesake. But it became a classic in 1971 when it graced the wrist of Steve “The King of Cool” McQueen, in the 1971 film Le Mans. And since there's not a guy alive who doesn't want to be like Steve McQueen, the model has become an enduring favorite among watch collectors.

The modern Monaco hasn’t changed much since McQueen. Today’s versions stay true to the same iconic square styling and red, white, and blue face, although the collection does include edgier all-black editions.

Elvis Presley

Hamilton Electric Ventura

This baby is nothing if not distinctive. The triangular face made its mark on the world in 1957, capturing the era's Atomic Age style of design into a "futuristic" timepiece.

The oddball design never really caught on to the broader watchmaking world, but it was a favorite of Elvis’. First seen on the wrist of The King himself in Blue Hawaii, the unique 50’s design was actually the world’s first ever electric watch. The brand still makes a model that looks strikingly similar to the original, as well as a few souped-up versions that are even more bold.

Humphrey Bogart

Longines Evidenza

The impeccably designed Evidenza was released in 1941 by watchmaking institution Longines. Shortly after, the timepiece made its big screen debut on the wrist of Humphrey Bogart in 1942’s Casablanca, right alongside the actor's enviable white dinner jacket, double-breasted trench coat, and easy elegance.

The modern version pairs an old school alligator band with a high-tech, anti-reflective, sapphire crystal face. Now that sounds like the beginning of a beautiful friendship.