The Icon, one of the most hotly contested of the Square Mile Watch Awards, is given to the brand that has successfully taken a horological classic and given it a fresh face.

It’s not easy: how do you reinterpret a watch that is already considered perfect? These are pieces that have stood the test of time, after all. You run the risk of losing fans if you depart too far from the norm, but change too little and you’ll be accused of being overly conservative.

Whether it’s a brand-new complication, a stunning redesign, or a commemorative model, the watches below have found that happy medium between giving the fans what they wants and staying true to the original design blueprint that gave the piece icon status to begin with.

Here’s this year’s contenders for The Icon award:

Audemars Piguet Royal Oak Perpetual Calendar Ultra Thin

Audemars Piguet Royal Oak Perpetual Calendar Ultra Thin

It’s difficult to sum up the brilliance behind Audemars Piguet’s latest creation without first returning to the original creator of the Royal Oak, Gerald Genta.

Such is his lasting influence on horology that almost 50 years after the 1972 release of AP’s iconic sports watch, the design remains one of the most popular timepieces on the planet. But how do you keep a stone-cold classic fresh? It starts with a heavy dose of innovation.

In the case of the Royal Oak Perpetual Calendar Ultra-Thin, it required five years of development from AP’s research division, saw a concept model released in 2018, and finally became available to the buying public in 2019.

Let us be the first to tell you, it was worth the wait.

Record-breaking watchmaking

So what are we looking at? The thinnest perpetual calendar ever made, wrapped up inside that handsome Royal Oak package.

It’s an astonishing 6.3mm in thickness (thinness?), thanks several space-saving innovations in the movement.

Most QPs boast a modular construction, which essential means that watchmakers add a separate module on top of an existing movement - counterintuitive when you’re attempting to slim down in size.

The AP Ultra-Thin does away with this by integrating the QP module into the movement itself and redistributing the parts horizontally, rather than stacking on top as in traditional perpetual calendars.

What’s not to love? Same old Royal Oak, now with record-breaking watchmaking.

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Grand Seiko SBGY003 20th Anniversary of Spring Drive

Grand Seiko SBGY003 20th Anniversary of Spring Drive

The Spring Drive movement has been ahead of its time for 20 years. Combining the might of a traditional mainspring, the accuracy of a quartz oscillator and the gliding second hand (controlled by an electromagnetic brake) that sweeps around the dial every 60 glorious seconds, Grand Seiko’s technology remains the closest horology has come to the perfect confluence of a hybrid watch.

Two decades of Spring Drive is a big deal for Grand Seiko, so it’s no wonder it feels like celebrating. There a four new commemorative watches rolling out this year – including platinum and yellow gold models – but we can’t resist the humble stainless steel version.

In comparison to the precious metal pieces, the steel offers GS’s fine attention to detail and access to its unique watchmaking without the need to blow the budget wide open. Indeed, you’ll struggle to find another brand offering a manually wound movement with a 72-hour power reserve and +1/-1 seconds per day accuracy for a shade under £10k.

The looks are pure Grand Seiko: a luscious silver dial featuring a radial sunburst guilloché pattern, simple baton markers, swooping lugs. It’s an exercise in less is more.

Here’s to another 20 years of the Spring Drive.

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Jacquet Droz Grande Seconde Chronograph

Jacquet Droz Grande Seconde Chronograph

Famed automaton maker Pierre Jaquet Droz first set up shop in 1738 - more than 100 years before the likes of Patek Philippe and Omega arrived on the scene - but were it not for the collective might of first Investcorp (1989) and later the Swatch Group (2000) bringing this brand from the brink of extinction, we might not be talking about the brand today.

The watch tasked with thrusting Jaquet Droz back into the spotlight? The Grande Seconde. First seen at Baselworld in 2002, this collection rose to critical acclaim for its careful blend of ornate detailing from Droz’s elaborate past with a cleaner, more contemporary aesthetic.

Originating from a 1784 pocket watch created by Monsieur Droz himself, the unique figure-of-eight design (intersecting an hour sub-dial with an oversized seconds register) is one of the most recognisable on the market today - and yet, some 17 years after its initial launch, the brand is still finding ways to catch our eye.

It’s somewhat surprising that it has taken so long for the Grande Seconde to house a chronograph complication, especially when the sparse dial configuration lends itself perfectly to the function, but Jaquet Droz has finally righted this wrong in its latest release - and perhaps created one of its most successful designs to date in the process.

A highly satisfying composition

The offset figure of eight sees chronograph and date complications added to the larger of the two registers. The former is a 30-minute counter (the seconds are shown on the one large hand that runs around the circumference of the watch), while the date display uses a retrograde red-tipped date hand.

Taking care of matters inside is the calibre 26M5R: a column wheel-controlled vertical-clutch movement that features modern touches like a silicone balance spring and lever for better accuracy and reliability.

The result is a highly satisfying composition that really allows the various components room to breathe - a departure from many ‘more is more’ designs we see all too often these days.

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Omega Speedmaster Apollo 11 Anniversary Limited Edition

Omega Speedmaster Apollo 11 Anniversary Limited Edition

It started with one small step for man and crystallised into one giant leap for watch marketing… The Speedmaster may have existed in some shape or form since 1957, but it will forever be immortalised by the events of 20 July 1969 when it accompanied Apollo 11’s commander Neil Armstrong and lunar module pilot Buzz Aldrin onto the surface of the moon.

It’s no surprise that Omega should celebrate the 50th anniversary of this momentous achievement with a special Moonwatch, but this is no ordinary limited-edition piece, this is one of the most collectible watches launched in the last decade.

Let’s make our way from the inside out: the impressive new Calibre 3861 is at the beating heart of this watch. Rumoured to have been in development for the last four years, this is a METAS-certified (Federal Institute of Metrology – aka, the most accurate place in Switzerland) Master Chronometer movement that features a co-axial escapement.

In layman’s terms, that means it offers greater accuracy over time and longer service intervals than your average lever escapement – and has passed Omega’s exacting reliability and chronometry tests to prove it.

This piece will be a sought-after collector’s item in the decades to come

On the design front, we’re looking at one of the most unique dials Omega has placed on the Speedmaster. It starts with a base grey dial and black sub-registers, but then it gets a little more interesting. The powerful image of Buzz Aldrin stepping down onto the moon has been laser engraved on the nine o’clock register - and forms the focal point of the piece.

This, along with the bezel edge and indices, has been created in a new 18k alloy Omega is calling ‘Moonshine Gold’ - a slightly paler yellow gold developed by the brand to preserve its colour over long-term wear. Suffice to say, this is no normal Speedie.

There’s another thoughtful tribute to the moon landing on the caseback where, laser-engraved onto an evocative moon-like surface, is an image of an astronaut’s bootprint. Armstrong’s legendary “That’s one small step…” frames the scene for added gravitas.

Unusually, perhaps the biggest treat is the presentation box, which includes an assortment of paraphernalia: mission patches, two engraved plates with landing site coordinates and landing time, and best of all a delightful lunar module display stand.

Thoughtful touches that will no-doubt ensure this piece will be a sought-after collector’s item in the decades to come.

There are few watches that match the historical impact of the Speedmaster, so it’s to Omega’s credit that it has met and perhaps even surpassed expectation with its Apollo 11 anniversary model.

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Rolex Yacht-Master 42

Rolex Yacht-Master 42

The Yacht-Master is the second youngest watch in Rolex’s famous collection and is perhaps the least well-known of its rosta of superstars. But its story is an interesting one, not least because it begins with a 1960s prototype chronograph that never saw the light of day.

The watch in question bore a resemblance to early Daytona models (created in 1964), but featured a larger 39.5mm case and regatta stylings on the dial. Why it never made it into boutiques only Rolex knows, but the story goes that just two examples now exist in the hands of collectors; nothing but a fascinating sidenote in the brand’s illustrious history.

Fast forward to 1992 and the Yacht-Master name makes its way onto a full-scale production model for the first time. During an attempt to update the look of its famous Submariner collection, the watchmaker’s designers stumbled upon the sleeker profile of what would become the Yacht-Master we know today.

While the utilitarian Submariner has an angular shape, the Yacht-Master features curved lines and softened lugs. It has an etched bezel insert, larger hands and is only water resistant to 100m metres (rather than the Sub’s 300m).

This piece oozes sporty appeal with dressy elegance thrown in for good measure

Rolex’s world-ready tool watches have defined generation after generation of style icons, but the Yacht-Master sets itself apart as something you might call a lifestyle watch: a timepiece better suited to lazing on yachts in Monte Carlo than scuba diving in the deep blue. It has its own aura and its own legion of fans as a result.

At Baselworld 2019, Rolex brought a new rendition of this model into the world, without necessarily reinventing the wheel. The new Yacht-Master 42 grows to a largest-ever 42mm case size and is dressed in an elegant monochrome colour scheme thanks to its 18ct white gold case, matte black Cerachrom bezel insert and black dial. Wrapped around the wrist with the brands rubberised Oysterflex bracelet, this piece oozes sporty appeal with dressy elegance thrown in for good measure.

Under those handsome looks is the state-of-the-art caliber 3235. Rolex's premier time-and-date movement uses a Chronergy high-efficiency escapement (an energy-saving answer to the traditional Swiss lever escapement) in order to regulate the watch to a highly impressive +2/-2 seconds per day – in short, crazy levels of accuracy for a daily beater.

From unproduced 1960s prototype to a happy accident at the turn of the century, the Yacht-Master doesn’t have the traditional Rolex storyline but its latest version goes to show that the Swiss giant still has tricks up its sleeve.

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