8 Best Vintage Rolex Watches To Enhance Your Style

Rolex is one of the most iconic premium watch brands in the world. With roots that take the company’s expertise all the way back to 1905 (when it was established as Wilsdorf and Davis), it has since become one of the most well-known brands in the world.

If you get a brand new Rolex watch today, then you’re likely going to need to spend a fortune, especially for the most gorgeous models they have available.

8 Best Vintage Rolex Watches To Enhance Your Style

However, with so much brand history, there are a lot of chances for you to pick up some vintage watches that can fit with any outfit you’re looking to create.

So then, if you’re considering picking up some vintage Rolex watches to enhance your style, you’ve come to the right article! In the sections below, we’re going to take you through a list of the best vintage pieces we could find, breaking down each one for you.

We’ve also made sure to include a short FAQ section that will help explain anything else you might need to know about Rolex watches.

The 8 Best Vintage Rolex Watches 

1. Rolex Royal For Emir Edition

This limited edition Rolex watch is a great option if you’re looking for something retro that will turn heads, even through its simplicity (for more information on vintage watches, check out our Vintage Omega guide). It comes with a leather material and stainless steel metal materials, as well as a gold-plated case. 

It’s a mechanical watch, so you’ll have to make sure it’s properly set to be accurate, but its simple analog display looks great.

It’s the kind of watch that doesn’t look like much at arm’s reach, but as soon as you peer a little closer you’ll have friends saying ‘is that a Rolex watch?

The only real downside of this watch is that it’s not water resistant, so you’ll have to be careful about when and where you use it. 

2. Custom Rolex Gold Stud Diamond

Next up we have the perfect Rolex if you’re looking for something decadent and gold-studded. Reminiscent of something from the 1930s, this watch is a great mixture between delicacy and flashiness.

It has an automatic, self-winding movement, and is made with Shappare glass and stainless steel. It’s a great, sturdy watch that we’d recommend if you’re looking for something that will go well with a flashy outfit with a vintage aesthetic. 

3. Rolex Submariner

The Rolex Submariner was first introduced in 1953 and has the unique design quirk of being water-resistant to up to 100m of submersion. It includes a 60-minute bezel that helped divers to keep track of how much time they’ve spent underwater.

These days, a Rolex Submariner is a cool accessory to any outfit. Submariners have a very distinct blue face with white dials that are sure to turn heads. Rolex Submariners generally have a silver and gold strap that is a great contrast to the more flashy blue color.

If you’re looking for a cool vintage watch, that is water-resistant and a good conversation point in social situations, then this is a great one to pick up! 

4. Rolex Daydate Chocolate Dial Watch 

If you’re looking for something that will work better for a fall/winter outfit, then this is a great choice for you! The Rolex Daydate is a great watch that gives a vintage, beige look for your wrist.

We’d recommend this one for cozy outfits like hats, scarves, gloves and winter coats. The Rolex Daydate is a vintage watch from the 1950s, with the first model being introduced in 1956.

You can get your hands on three different sizes of case diameter, including 36mm, 40mm and 41mm. 

5. Rolex Datejust Classic Watch

Are you looking for something distinctly Rolex? If you want something that is a classic, and what comes to mind for many when they think of vintage Rolex watches, then the Datejust is going to be a great choice for you.

The Datejust was first created in 1945 and became renowned as the first ever self-winding waterproof wristwatch that displayed the date in a separate window on the dial.

This made it a hot watch to own at the time, and they have only increased in value ever since. We’d recommend checking out this watch if you want something that looks classy and goes with a wide range of different outfits. 

6. Rolex Cellini 18k Gold Mechanical Watch

The original version of the Rolex Cellini came out in the year 2000, and it’s a great way to get a reminder of the 2000s into your outfit. This simple, delicate watch is made from 18k gold and comes with a gorgeous champagne dial with gold batons.

It has a very simple timepiece that makes telling the time easy. It is worth noting that this watch requires daily checking, but it’s a gorgeous choice for daily wear! 

7. Rolex Lady-Datejust

Looking for something truly elegant? If this is the case, check out the Rolex Lady-Datejust, which is one of the most impressive watches that Rolex has to offer. It was first unveiled in 1957, and has been one of the most popular models ever since.

Because of this, there are lots of different versions you can have, each made with different materials and gemstones. However, each version of this watch is clearly expensive and lavish, so it’s best worn with formal evening outfits. 

8. Rolex Air-King

Just as the Rolex Submariner was a love letter to nautical style and efficiency, so too is the air-king, but for aviation! The Rolex Air-King is a great choice if you’re looking for something precise, metallic and gorgeous.

These watches are a great choice to wear on a summer day with a vintage sportswear outfit, or for a more formal uniform. The Air King comes in a 40mm case in Oystersteel and a solid-link Oyster bracelet with a black dial.

This is a great choice for something slick and stylish. 

Final Thoughts

So that was our list of the 8 best vintage Rolex watches we could find that will enhance your style.

Rolex watches can be pricey and difficult to get ahold of, but each one of them can act as the centerpiece of your outfit that will turn heads and transform simplistic fits into something much more interesting.

Just note that with all of the vintage pieces we mentioned above, there are many different versions of them, as in the past many were custom-made or had custom parts.

We hope that this article has told you everything you needed to know about the best vintage Rolex Watches. If you still have some questions, make sure to check below for our extensive FAQ that will teach you some additional information about vintage Rolex watches.

We wish you the best of luck on your vintage fashion journey and hope that you find some incredible accessories to complement your outfits! 

Frequently Asked Questions

How Can I Tell The Age Of My Rolex Watch?

Rolex does a good job of making sure that the year of design is etched somewhere on the watch. Generally, you can find this through the serial number, which can be located at the back of the timepiece, or on the side of the strap. 

Do All Rolex Watches Have Diamonds?

Not all Rolex watches have diamonds in them. Diamonds are some of the most expensive gemstones that you can come across, so Rolex watches will typically only feature them in their custom versions.

It’s possible to get any Rolex watch encrusted with diamonds, provided you have the funds available. 

Do Vintage Rolex Watches Continue To Be Valuable?

You’ve probably heard the expression that a good watch is like an investment. Watches are well known for holding their value across long periods of time.

In fact, some of the most pristine versions of the watches we listed above might end up costing much more than they originally did. The age of a watch can be seen as a selling point, especially if it has a lot of unique design in it or additional expensive features/components. 

How Much Should I Expect To Pay For A Vintage Rolex Watch?

Rolex is one of the most premium watch brands in the world. Depending on the watch you’re looking at, you can expect to pay a lot of money for them.

However, since we’re talking about  vintage watches, there’s a chance that you can get an older version—especially one that hasn’t been kept in good condition—for much less cost. It can be difficult to find a Rolex watch at a good price, so it’s important to shop around! 

How Can I Be Sure My Rolex Watch Is Authentic?

If you’ve bought a Rolex watch from a respectable retailer, you can probably rest easy that it’s authentic. However, if you’ve bought one second hand then you might need to double-check the serial number placement and quality of the watch. 

Willa Price
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