The Playbook For The Modern Man

The Best Rolex Watches To Buy In 2020

Do the Rolex sweep.

‘Aspiration’ is a word that is often used when we talk about watches. Something that shows others who we are, where we’re at, and the direction we’re heading in. What a Rolex says is something a little different, things like ‘I’ve made it’, ‘catch me if you can’ and ‘I bet you wouldn’t mind being me?!’

Although most people will associate Rolex with Switzerland like the majority of major watch manufacturers, the brand was actually founded in London, England, in 1905. Back then the company was called Wilsdorf and Davis. It wasn’t until after the First World War in 1915, when the company upped sticks and moved to the more neutral (and more tax-friendly!) surroundings of Geneva that the watchmaker took on the name it is so fondly known as today.

Since those humble beginnings, Rolex has led from the front in terms of design and innovation. In 1926 they produced the world’s first-ever waterproof watch, the Oyster, with its airtight casing that ensured optimum movement when in and around water, and even sat on the wrist of Mercedes Glieitz as she swam for 10 hours non stop across the English channel. This flirtation with swimming propelled Rolex into other sports and even aviation – and was seen by many during the era as the innovative time teller for innovative times.

In more recent years Rolex has been about perfecting their creations, incorporating small, yet effective, details into their designs to maximise functionality, practicality and overall aesthetic – whilst testing the limits of an everyday watch.

Because of their luxury and high-end nature, and the fact they’re assembled by hand, means Rolex watches are often found in limited supply. On top of this, the only way of ensuring you get an authentic piece is to buy from an official Rolex retailer. If there’s a particular model you’re after, we recommend scouting out your retailer of choice, build up a relationship and get your order in as soon as possible.

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RELATED: Rolex Watch Prices You Can Expect To Pay In 2020

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Here we have gone through ten of our favourite – and reasonably affordable – pieces to help you find your perfect men’s Rolex.

Explorer II

Reference number: 216570
Case material: Oystersteel
Price: AU$11,700

Best Rolex Watches Men - Explorer II

The Explorer II was designed, as you might expect from the name, to accompany polar exploration teams in some of the coldest, most extreme conditions on the planet. It is made from Oystersteel which was specially developed by the brand using 904L steel, an alloy more closely associated with the aerospace and chemical industries where corrosive resistance is imperative. It has a traditional Rolex face with 18ct gold hour markers. The piece also features a 3187 self-winding mechanical movement, enveloped in a 42mm case with sapphire crystal lens. The bracelet and clasp, even though made from steel, is actually adjustable by up to 5mm to help you adapt to different usages, situations or surroundings.

Datejust 41

Reference number: 126300
Case material: Oystersteel
Price: AU$11,100

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Best Rolex Watches Men - Datejust 41

A piece that was first created for water sports but is equally as capable of being a daily wearer. First launched in 1945 as the very first self-winding watch to display the date in a window at the 3 o’clock marker, the Datejust 41 has gone on to become a staple in Rolex’s repertoire.  It features a five-piece Jubilee bracelet with a design that dates back its ancestors, so what you’re getting here is a little slice of Rolex history. The 3235 movement is protected by an Oystersteel case, whilst scratch-resistant sapphire protects a distinctive Rolex black dial with date and cyclops lens. It’s water-resistant for up to 100 metres, but this thing looks great whether you’re in the water, on your boat or even in the office – a real classy allrounder.

Sky-Dweller

Reference number: 236935
Case material: Everose Gold
Price: On request

Best Rolex Watches Men - Sky Dweller

This is easily one of the most complicated watches – in terms of function and how it’s made – that Rolex has ever produced. It’s designed for the international businessman that needs to know both the time in his current location along with the time back at home in the office. This version was first developed in 2005, when Rolex started to take control of and revolutionise their materials and formulas, resulting in Everose Gold, with its rose-tinted hue. This highly sought after watch is a Rolex classic, with the brand still very secretive about exactly how the colour is produced.

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Oyster Perpetual 39

Reference number: 114300
Case material: Oystersteel
Price: AU$8,000

Best Rolex Watches Men - Oyster Perpetual 39

This is perpetual motion direct from the hands of watchmaking masters. Nearly all of the components in this Oyster Perpetual 39 have been designed, manufactured and assembled in house using materials developed exclusively by Rolex. A deep blue dial covers a 3132 self-winding movement encased by a sleek 32mm Oystersteel case. It features a beautiful Oyster bracelet that was first developed by the brand back in 1930, with its three-piece links that have been copied by many but never perfected in the same way. Hour marks are characterised by 18ct gold to add that touch of elegance to a watch that is fantastic value for money.

Milgauss

Reference number: 116400GV
Case material: Oystersteel
Price: AU$11,700

Best Rolex Watches Men - Milgauss

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If you’re looking for a watch with a more sporty design that looks as good on the golf course as it does behind the wheel of a sports car, then this Milgauss design will tick all the boxes whilst adding a touch of class to boot. A 40mm Oystersteel case protects a 3131 self-winding movement, both exclusively designed in-house in Geneva. Luminescent hour markers on the 3, 6 and 9 are read with hands made from green sapphire crystal. There is also a ferromagnetic shield within the case that deflects magnetic interference that can play with function, meaning time is never compromised. An effortless marriage of style, practicality and comfort.

Submariner

Reference number: 114060
Case material: Oystersteel
Price: AU$11,100

Best Rolex Watches Men - Submariner

This classy, robust model has everything you imagine when you think of a Rolex. From its distinctive dial to its solid unidirectional bezel, it’s a watch that is wonderfully timeless in its design. It features a self-winding perpetual mechanism covered by an Oystersteel case with a sapphire crystal lens. The bracelet is fitted with an Oysterlock clasp which prevents accidental opening, perfect for those days out on the water riding the swell. A glide lock allows you to adjust the width for diving, and its sheer comfort means that it almost goes unnoticed under a suit. This magnificent design is made for men who enjoy the open waters.

Explorer

Reference number: 214270
Case material: Oystersteel
Price: AU$9,150

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Best Rolex Watches Men - Explorer

The original Explorer is thinner than its sister version with a 39mm Oystersteel case. It offers resistance in the most extreme conditions for total reliability whenever you’re on the go. Its smooth bezel holds a sapphire crystal layer across a distinctive yet simple Rolex dial. A 3132 movement – designed and built in house – features a Parachrom hairspring and Paraflex shock exporters that maintain high functionality across challenging terrains. But this watch doesn’t need altitude and snow to be fully appreciated, as it looks great whether you’re at work or winding down during a weekend away.

2019 Yacht-Master

Reference number: 226659
Case material: Oystersteel/ White Gold
Price: AU$40,750

Best Rolex Watches Men - New Yacht-Master

One of the newest standout models in the Rolex range is this New Yacht-Master, an exemplary watch designed for sailing professionals. The piece was inspired by British yachtmen and aviator Sir Francis Chichester, the first man to solo his sailing boat around the globe in under a year. It features an entirely new generation of movement, the calibre 3235, protected by a beautifully designed white and gold oyster case. The watch features a flexible bracelet for testing ocean waters and a 60-minute Cerarachrom bezel made from polished ceramics. A chroma light display also makes the hands and markers highly visible against a jet black dial for excellent readings in low light.

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GMT-Master II ‘Pepsi’

Reference number: 126710BLRO
Case material: Oystersteel
Price: AU$13,600

Best Rolex Watches Men - GMT-Master II

The GMT-Master II was first launched in 1954 to be used by Pan American Airway pilots during their international flights. The watch has since gone on to become a Rolex classic, characterised by its two-tone red and blue, 24-hour rotatable bezel. It’s designed with a classic Rolex Jubilee bracelet that holds a 42mm Oystersteel case against the wrist. It also features an adjustable Oysterlock clasp with 5mm comfort extension. There may be a lot of classic Rolex designs on the market today, but few are as iconic and as recognisable as the GMT-Master II.

Cosmograph Daytona

Reference number: 116500LN
Case material: Oystersteel
Price: AU$18,500

Best Rolex Watches Men - Cosmograph Daytona

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This mechanical Cosmograph is inspired by the Florida race circuit Daytona, which was seen as one of the biggest tests for aspiring racers in the 20th century. The watch was made for complete accuracy so that drivers or pit chiefs could quickly and easily take down both current and elapsed track times. The chronograph is controlled by an activated pusher that clicks when started or stopped. A 40mm diameter ensures it doesn’t feel too large on the wrist, whilst a sleek Oystersteel case protects its revolutionary 4130 movement. If you’re going to go out on track anytime soon then the only watch you will want behind the wheel is this wonderful Cosmograph Daytona.

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  • James

    The problem is that many of the above-mentioned watches – particularly ones such as the GMT II, Daytona and Submariner – are simply not available in retail stores.
    Therefore, people have three choices:
    – Buy several other Rolex watches that you do not actually want so that the store will put you on a waiting list so that, at some stage, you may have a small chance of actually being able to buy the watch you want;
    – Buy a “grey market” watch, most likely at a considerable mark-up;
    – Buy a used Rolex, and still quite possibly pay more than retail anyway; or
    – Refuse to play the game and either get another watch or just use your phone to tell the time.

  • Greg Maxim

    Yes the are you clearly just don’t know where to shop. Rolex stores carry there entire lineup idk where this retard is getting his information.

  • Jack West

    Hi Max, Mercedes Glieitz wore the Rolex Oyster on a chain around her neck while swimming the English Channel in 1926. Wearing it on her wrist would have impeded her ability to sein.

  • James

    Greg – Thanks for the diplomatic and courteous response! 😉

    Based on my own experience and numerous people I know spread across several different countries, I disagree with you.

    There are both Rolex boutiques, and authorised Rolex dealers, that will either tell you that they simply do not have stock of the more popular stainless steel sport models, or they will tell you that they will not sell you one and that, if you wish to buy one, you must have a history with the store. In other words, you must either buy a number of watches at one time (typically including less popular watches) or you must buy a few watches over time to build up a relationship.

    This may not apply to all Rolex boutiques and Rolex ADs, but it applies to quite a large number. It’s for a few reasons – actual lack of supply of popular watches; ability to leverage popularity of certain models to sell less popular models; and desire to build up a history with a customer so as to make it less likely that they will walk out of the store and almost immediately “flip” the watch on the internet for thousands of dollars more than they paid for it.

  • Cam

    See Greg, James and I could agree with you but then we would ALL be wrong….

  • paul

    haha has this retard been in a Rolex AD lately? Every single one of them looks like they’ve just been robbed

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