Five of the Best Entry-Level Rolex Watches

by   |  in Accessories

Whether it’s the sky-high prices or undeniable lore, the world of Rolex watches can certainly overwhelm first-time buyers. 

In this article, I showcase how accessible the brand can actually be if you stick with these five models. They’re among the best entry-level Rolex watches, all things considered. I promise you, buying your first isn’t as daunting as the cultural gatekeepers may have you believe –and it’s also really fun. 

Owning a basic Rolex watch gives you an effortless option to elevate even the most thrown together mornings.

best entry level rolex - black dial submariner with vintage electronics
Rolex Submariner photo by Ern Gan on Unsplash

No one Rolex is inherently better than another, and there’s a model for every type of guy. An entry-level Datejust is manufactured as discriminately as the Paul Newman Daytona that Phillip’s auctioned off for $17.8 million USD.

Choosing a Rolex is about what’s best for your needs, and the person you are (or want to be!). 

As such, I’ve chosen five iconic lines that are versatile and affordable, but differ in their historical significance, story and aesthetic. 

But first… 

Why Are Rolex Watches So Expensive?

The science and art that go into fashioning a Rolex watch make anything Q has ever given James Bond look like a Chinese finger trap. 

Rolex watches are expensive for two general reasons: Because of their over 500 patented in-house innovations and because Rolex avoids quality-compromising shortcuts and materials.

white dial rolex yacht master with blue bezel in snow
Rolex Yacht Master photo by Nicolas Cool

Some quick examples:

  • Rolex movements are unrivaled in precision and longevity. The movement is a big part of what makes a Rolex a Rolex. They manufacture their own automatic mechanical movements in-house, a laborious skill. Most watch manufacturers outsource their movements. 
  • Rolex has strict standards when it comes to raw materials. Today, Rolex uses a 904L stainless steel, their proprietary Oystersteel, which is rust-resistant and shinier than the more abundant 316L stainless steel that many luxury brands use.
  • Rolex watches are certified Chronometers. The Contrôle Officiel Suisse des Chronomètres, subject each Rolex watch to 15 days of testing for resilience and movement-accuracy in different conditions including temperature and air pressure.

So we know they’re durable, which leads us to the next question:

How Long Do Rolex Watches Last? 

Your Rolex can one day be your son’s Rolex, and his son’s after. They need to be serviced every 10 years, and Rolex watches are famously maintenance-friendly.


eBay just rolled out its own authentication service: Authenticity Guarantee. Now you can buy that incredible pre-owned, vintage Rolex and feel confident it’s the real deal.

Are Rolex Watches Overpriced? 

If being part of Rolex’s fabled world isn’t worth the price of entry for you, the best empirical measure is comparing them to similar luxury brands that likewise boast proprietary features.

A new entry-level Patek will set you back $10,000-20,000. All of the Rolexes on this list are under $10,000. Not too shabby!

What is the Cheapest Rolex? 

When it comes to brand new watches, the answer is often the Air-King. Even with entry-level Rolex lines however, “special” features will pile on the zeroes to your bill like adding guac to a burrito order.

So if you’re trying to go as low-priced as possible, then avoid any frills:

  • Avoid limited edition watches. A quality as minute as a special edition bezel color can easily quadruple the price of a Rolex, sometimes despite the condition it’s in.
  • Always opt for stainless steel. Remember, Rolex patented an excellent Oystersteel. Any watch can be made of gold and silver, but a Rolex watch made of their proprietary material is, in my opinion, more of a Rolex. They’re also sturdier and will hold their value better.
  • Avoid ornamented dials. Price aside, simple metal dials are simply more quintessential any way!
  • Consider looking on eBay first. You’re bound to find deals there, and with Authentication Guarantee, you don’t have to worry about duds or frankenwatches.

Rolex Sport Watches: The Best Entry-Level Rolexes

The best entry-level Rolex watches for men tend to be sport watches. Why though? 

Well, when watchmaker Hans Wilsdorf founded Rolex in London in 1905, he imported Swiss movements to provide high-quality utilitarian wristwatches in a world of dressy pocket watches. This pillar carries on today. 

black dial rolex explorer on black reflective table closeup
Rolex Explorer photo by Carlos Esteves

So, what makes up a good entry-level Rolex? 

Unless otherwise noted, all the entry-level Rolex watches below feature the following:

  • 904L stainless steel body AKA the proprietary Oystersteel.
  • Scratch-resistant crystal sapphire to protect the dial.
  • COSC certification.
  • Parachrom hair spring (for modern models). 
  • Paraflex shock absorber.

Now let’s see the watches!

Option 1: Rolex Oyster Perpetual

This watch changed the industry, yet it’s so understated. Unsurprisingly, the Oyster Perpetual is for the classicist. The minimalist.

rolex oyster perpetual steel watch with white dial
Rolex Oyster Perpetual photo via Jomashop

When you wear an Oyster Perpetual as your first Rolex, it won’t immediately pop out to people. It will be as if you’ve been wearing Rolexes all along. 

The Oyster Perpetual was the world’s first automatic winding wristwatch (that’s where the “perpetual” comes in). Today, the Oyster Perpetual features almost every innovation that makes Rolex legendary. 

Because it’s been around for so long, there are several reference numbers. However, I want to direct entry-level buyers to modern models of the line, the path of least resistance. You can get a great deal with vintage pieces, and vintage definitely has a cool factor about it, but it’s too easy to get ripped off. 

A new Oyster Perpetual is only around $5,000-6,000, and pre-owned modern Oyster Perpetual watches can be much less. The Oyster Perpetual 39 mm 114300 is a good starting point. 

Rolex Oyster Perpetual

"This watch is the direct descendant of the original Oyster launched in 1926, the first waterproof wristwatch in the world and the foundation on which Rolex has built its reputation." –Rolex

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Features and qualities of the Oyster Perpetual include:

  • Water resistant up to 100 meters; the Oyster Perpetual is a descendant of the 1926 Rolex Oyster, the world’s first waterproof watch.
  • A minimalist, easy-to-read dial.
  • The quintessential Rolex 3130 calibre, as accurate as Lionel Messi on the soccer field.
  • Design highlights include an un-fluted bezel and 18 ct gold hour markers. 

Rolex also offers Oyster Perpetual reference numbers with several design tweaks such as dial color, Arabic and Roman numerals and size.

Option 2: Rolex Air-King 

This next statement is going to be controversial, but the Air-King is less of a Batman, and more of a Robin. Hear me out: Some of us are more of a Robin, and proud of it.

best entry level rolex air-king with steel case bracelet and champagne dial
Rolex Air-King photo via Jomashop

Often, collectors recommend Air-Kings with pause because it’s considered an “overlooked” line, and has been called a “boy’s watch.” 

But I truly believe there’s a Rolex out there for every kind of guy, and some men really value impish and boyish qualities. The Air-King is a sophisticated way to express those values. 

It’s the cheapest of any new entry-level Rolex, starting at around $5,000. 

The Air-King was first introduced in 1945 as a tribute to the pioneers of flight. Again, I recommend focusing on modern models of Air-Kings. The current reference number is 116900.

Rolex Air-King

"The Rolex Air-King pays tribute to the pioneers of flight and the Oyster’s roles in the epic story of aviation." –Rolex

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Features and qualities of the 40mm Air-King include:

  • Water resistant for up to 100 meters.
  • A bold dial with Arabic numerals, marked by a distinctive signature triangle marker at the 12 o’clock position, a bold green second hand and Mercedes-style hour hand.
  • Calibre 3131 automatic mechanical movement
  • Design highlights include bold green accents, the title “Air-King” in the same vintage 1950s font as the original.

With the Rolex Air-King’s big Arabic numerals and bold green accents, it’s as if your favorite toy airplane from childhood Autobot-transformed into a sleek gentleman’s watch.

Option 3: Rolex Explorer I and Explorer II 

The Duke of Sussex wore two watches when he was in Afghanistan. One of them was a Rolex Explorer II. 

rolex explorer ii watch with white dial and steel case and bracelet
Rolex Explorer II photo via Jomashop

The Explorers are rugged sport watches known for durability on the field, but these days more in a pheasant-hunting-in-the-English-countryside kind of way due to its rich heritage. The Rolex Explorer famously accompanied Sir Edmund Hillary and Tenzing Norgay on their historic climb of Mount Everest in the 50s.

I’ll lay my cards on the table and mention that the Explorer II is my go-to everyday watch, so I’m a bit biased. 

The 42 mm version can be polarizing; purists claim the Explorer lacks versatility because it isn’t appropriate for fine dining. I disagree with this (it’s a Rolex, people).

At strictest, formal affairs technically call for watches with leather straps, but I don’t think anyone would bat an eye at any well-kept Rolex either, particularly one as handsome as an Explorer.

The Oystersteel elevates the Explorer design, so I again recommend going for the modern versions, which will cost $6,500 for an Explorer I and $8,350 for an Explorer II, new.

Rolex Explorer

"Some of the world’s most intrepid explorers, mountaineers and scientists took Explorer and Explorer II watches to places that tested their reliability in the toughest conditions." –Rolex

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Features and qualities of the Explorer II 216570 and Explorer I 214270 include:

  • Water resistant up to 100 meters.
  • The Explorer II features a date Cyclops on a white or black face, and Mercedes-style hour hand.
  • The Explorer I doesn’t feature a Cyclops and features a black face.
  • 3187 calibre for the Explorer II, 3132 for the Explorer I.
  • The Explorer II features a 24-hour bezel, while the Explorer I features Arabic numerals at the 3, 6, and 9 o’clock positions.
  • The Explorer I has a 39 mm case, while the Explorer II has a 42 mm case.

Option 4: Rolex Datejust

The Datejust is the only dress watch on the list and there’s certainly something ceremonial about it. If the Datejust were a party, it would be the White House Correspondents Dinner.

best entry level rolex - vintage two tone gold and steel rolex datejust with gold dial
Two-tone Rolex Datejust via Jomashop

The Datejust was originally created to commemorate Rolex’s 40th anniversary. Naturally, the date Cyclops that this upscale watch is associated with is patented by Rolex and is the feature that unifies the many iterations of this iconic line. 

The Datejust is a fancy watch. It isn’t, however, just for fancy occasions. In the grand tradition of Rolex, it lacks over-the-top accouterments, so the Datejust can easily be dressed down or up. 

Partly for price reasons and partly because the Datejust is a traditional, timeless watch, I advise entry-level buyers to seek vintage Datejust Rolexes from the 60s and 70s, such as the 1600 and the 1601. 

They were highly sought after and heavily produced, so there is abundant supply. They usually cost $3,000-$4,000 with variance. 

Rolex Datejust

"The Oyster Perpetual Datejust is the epitome of the classic Rolex watch." –Rolex

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Features and qualities of a vintage Datejust include: 

  • Variety with every reference number: An endless selection of designs, bezels, dials, sizes, material and bracelets.
  • The 1600 and 1601 vintage Datejusts have a 1570 calibre. Rolex stopped using this calibre in the 70s, but it’s perfectly reliable and is indeed a certified Chronometer.
  • Design highlights include the characteristic date window at 3 o’clock beneath the Cyclops lens and a fluted bezel. 

To be extra traditional in formal situations, you may wear the Datejust with a leather strap. I think it even looks good in a suede strap (pair with suede shoes, perhaps!). Very versatile!

Option 5: Rolex Submariner

The Rolex Submariner is like Sinatra: Commercially popular, instantly recognizable, but of genuine quality and genuinely timeless.

rolex submariner with black dial and steel case and bracelet
Rolex Submariner via Jomashop

If you choose a Submariner, you certainly won’t be the only one in the room with one on, but don’t let this deter you if you think the Submariner is right for you. After all, Sean Connery and Steve McQueen aren’t bad company.

The Submariner was created in 1953 as a tool for divers, the first waterproof watch at 100 meters. This sport watch has been a staple of high-caliber watch auction catalogs since then.

I recommend both vintage and modern models of this archetypal line. Certain vintage Submariners are definitely beyond the entry-level price range, but the 5513 is often under $10,000, though it isn’t COSC-certified. The modern Submariner Date features a date Cyclops, but the regular Submariner, 11460, does not. 

And not that I encourage entry-level Rolex buyers to think about this, but the Submariner is one of the safer bets when it comes to investment. 

Rolex Submariner

"In watchmaking, the Submariner represented a historic turning point; it set the standard for divers’ watches."

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Features and qualities of the Submariner include: 

  • Water resistant for up to 100 meters.
  • A dial with contrasting colors from the hands, a Mercedes-style hour hand, and luminescent markers.
  • The vintage 5513 has a calibre 1520, the modern Submariner 11460 has a calibre 3130, and the Submariner date is 3135.
  • Design highlights include effective lume brightness even underwater.
  • Divers can time their dives using the rotatable 60-minute bezel with scratchproof Cerachrom ceramic insert.

So, which entry-level Rolex is right for you? 

The only person who can answer that question, naturally, is you. All you need to do is think about who you are, what’s important to you and what role this entry-level Rolex will play in your life. Most importantly though, have fun.

I hope my advice was helpful in your journey to your inaugural Rolex acquisition!

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