Rolex prices have been soaring for the last 20+ years.  Rolex investments have had the opportunity to pay off nicely for the Rolex owner with some skill and negotiation.  

Not every Rolex investment will generate a positive gain.  

Although every Rolex has value, not every Rolex has the same value to collectors and investors.  The Rolex Daytona is highly sought after, but shines like a bright star over less sought after Rolex watches.  For example, the Milgauss or even the standard Oyster Date-Just will not fetch much attention by investors.  And therefore their prices have sagged to much lower levels.  

Rolexes Hold Their Value But Can Drop From the Original Price.

One of the greatest things about Rolex is the ability for them to hold their value.  Especially well cared for timepieces, can still appear new, and retain their value.  Unlike a car that depreciates quickly, a Rolex will not depreciate as fast.  And over time, a vintage Rolex can start rising in price.

• Seek the Help of Professionals - Watch Collectors know what is hot in the market.  They know what to look for in order for an investment to rise in price.  They know for instance, whether it is better to own a Submariner with or without the date, or whether a steel case is better than a gold one.  They know how rare a timepiece is by the amount of components that are produced each year of that model.  They also know what things collectors and the market in general are looking for.  Just as you would look to a quality broker to recommend a stock, looking at a professional for watch investment advice is critical.
• Take Care of Your Rolex - Make sure you clean and maintain your Rolex.  It is important to know that you are not only looking to make the timepiece last for you, but also for its future owner - whether that be to someone you sell it to, or gift it to.  
• Let Rolex Service The Timepiece - Vintage timepieces may not need to be serviced as frequently.  However, new timepieces can increase in value if you prove that it has been serviced recently and often by Rolex Certified Professionals.  

Avoid these Rolex Traps When Investing in Rolex

• It isn't all about the bling - Some Rolex timepieces are encrusted with an endless supply of diamonds and other gems.  However, collectors don't value the timepiece based on the number of dimonds.  In fact, all-steel Rolexes may rise in value faster than a timepiece worthy of a Rap Artist.
• Pay Attention to the Price - One of the best ways to make a positive investment is to get a quality price.  You can win just by buying when there is a discount.  Basically if you bought a Rolex Daytona when nobody was buying them in the 1960's and 1970's, you would have made a huge profit if you sold it today.  There are many discount vendors who buy wholesale from authorized Rolex Distributors when the price is right.  This means that the 40-50% markup might drop to 10-20%.  So, if you bought at the lower markup, you will have a much better chance at turning a profit.  
• Cheaper Isn't Always Better - Just because a Rolex is cheap, doesn't mean that this is the right one to buy.  It could be cheap because the demand is non-existent. 

A recent story was told by Paul Alteri of Bob's Watches.  It was of a Canadian woman who purchased a 2nd hand couch for $25 at a thrift store and found a Daytona 6241 Paul Newman, worth millions, in between the cushions.   

Ok.  So, it is pretty obvious that from a price perspective, finding an old Rolex Daytona would probably be first on everyone's list.  However, let's take away the profit potential from the equation here.  Let's say, you had an opportunity to happen upon a Rolex timepiece and that timepiece would have the highest resale value of any timepiece sold.  Here you get to make the decision based purely on aesthetic reasons.  Which one do you like better?  Which one would you rather find, whether it be to wear it yourself, or to gift it to someone you care about?

Here are my top three.  

The Rolex Yacht-Master is one of the timepieces I would most like to find because of it's absolute beauty and distinctive appeal.  I don't own a yacht.  I love boats.  Although this would not be the first timepiece on my "buy list", I would certainly love to own one.  

Wearing a Yacht-Master shows you have taste, culture and style.  You are seen as a man or woman of ultimate leisure - who appreciate the finer things in life.  

The Red, White and Blue are not only highly legible and readable, but it is also an American icon and color palette.  You honor more than yourself when you don this beautiful timepiece.

The Rolex Sky-Dweller is another timepiece that would not be first on my buy list.  However, it is stunning and practical.  The rotating dial adds huge visual appeal to it.  I think I admired it even more when I saw LeBron James showing off this timepiece - of course in Gold.  Frankly, I am perfectly fine with finding a steel version of this one in my couch with the dark blue with luminescent hour markers and date window.  

The Rolex Sky-Dweller is ideal for travelers.  The 2nd time zone in the center dial and big red triangle makes it easy to see both your current time zone and your home base zone at one glance.  I love the fact that it represents the 2nd zone in 24 hour markers.  It has a militaristic appeal allowing you to track in 24 hour marks rather than just relying on notations of AM or PM.  The sophistication and intricacy that went into the development of this caliber is incredible.  

As if this was not enough, there is a MONTH calendar around the actual dial.  So, not only do you get the day of the month aperture at 3 o'clock, but the hour markers can show you what month 1-12 you are in.  A red square appears above the hour marker for the month you are in.  Pictured above, you can see it is in the 11 o'clock position, indicating November. 

#1 Rolex Daytona with Black Rubber Strap and Gold Case, Champagne Dial.  

If you read through some of my blogs, you will see that this is a timepiece that I absolutely love.  It is a Rolex Daytona with gold and black coloring throughout.  It is spectacular in every way.  Not only does it have a timer and complexity with its pushers at 2 and 4 o'clock, but it is absolutely one of the most stunning timepieces you could own from the Rolex collection.  

Even though most collectors are looking for vintage Daytona's and this one would hardly compare in resale value, this is what speaks luxury, and exceptional style.  The black and gold is very masculine and not over the top with gold.  It is comfortable to wear, because of the rubber band. The champagne dial looks unbelievable against the black inner dials and black and white luminescent hour markers.  I love how you get hour markers all around the dial with the exception of the 12 o'clock position where the crown sits.  Most Rolexes drop the 3 o'clock hour marker because of the date aperture.  

The black bezel with gold markings finish off the timepiece.  It makes me want to get out on the highway and drop the foot pedal to the metal.  

It is a cut above the standard steel Daytonas.  The golden luxury makes this timepiece look good any time day or night.