I have been buying and collecting watches for 20 years, and refurbishing and selling high end watches for over 10 years.  The two most important points of advice I could give someone regarding watches are: Almost always, you get what you pay for...and, if you buy a quality, pre-owned watch, and maintain it in good condition, your watch will act as an investment.
I am 35 years old and I have had an interest in watches since I was a child.  Almost anyone that knows me is aware that I am a watch "snob".  And every one of those people also have asked me "How can you justify paying that much money for a silly watch?"  Every now and then, a buddy will say "I just don't understand you, my $20 Timex works just fine". 
Listed below are the three points that I will argue in the Rolex vs. Timex debate.  Individually, none of them are enough to support my argument....but collectively they provide some rational support for the Rolex, or other high end watch.
This is a very simple one.  You get to use it.  You get to wear it.  People get to see it.  Although many people will deny it, one of the most compelling reasons to wear a nice watch is the prestige.  If you are at a wedding or a reunion, you just want people to see it.  If you are a businessman, a nice watch symbolizes your success.  This is the most obvious reason why one might want to own and wear a high end watch, but it's not the most important reason.
Like I said...you get what you pay for.  A high end watch will last for years and years, and can be passed down as a family heirloom from generation to generation.  Quality watches are more durable and can better withstand wear and tear.  They will run for years and years, and with a little TLC and maintenance, they can be kept in like new condition.
On the other hand, low end watches wear quite easily.  In many cases, wear or damage is irreparable.  Most inexpensive watches will end up in a landfill after only a couple years.  Many people even call them "disposable" watches for this very reason.
As a general example, a rough guess would be that 99% of Rolex watches are probably still in use after 25 years....while perhaps 99% of Timex watches are in the garbage within the first 10 years.
Let me provide a great example.  My biggest problem is that I have a bad habit of constantly smashing my watch into metal door frames in my work office. If I wore a Timex, each time I did this, a huge scratch would inevitably be added to the watch.  However, my Rolex GMT Master does not get a scratch.  Instead, IT MAKES A SCRATCH on the door frame.  Every Rolex or Omega watch I have known someone to wear for any extended period of time has maintained its original “like new” visual appearance for years. 
The end result is that a high end watch could literally outlive you and your children, and you might keep the same watch for decades rather than buying a new $25 or $300 watch every couple of years. 
A high end watch’s investment appeal is probably the most compelling reason to own a quality, pre-owned watch.  Prestige and quality won’t convince your spouse to agree with this argument.  But a pre-owned watch’s ability to appreciate might be convincing.
Let me start by giving a personal example.
At 26, I bought my first Rolex even though I could not afford many other luxuries of life.  I sold that watch a year later (at a 40% profit) because I wanted to upgrade.  A few years later, I purchased a Rolex GMT Master with box and papers for $2000, and I have been wearing that watch almost every day for the last 6 years.  Today, 6 years later, that watch is worth about $3600.  On the other hand, that $20 Timex that my buddy bought 6 years ago is now worth, well, nothing.  He threw it in the trash two years ago.  And the $300 Seiko my other friend bought is now worth about $40.
Many people don’t realize this, but appreciation of the value of many watch brands is a proven fact.  Retail prices for Rolex, Omega, Breitling, and others, increase every year.  The relative style of most of these high end watches remains consistent.  As a result, as the pricing of new models increases, the demand for pre-owned watches also increases.  Higher demand = higher prices.  The math is easy.  In the last 5 years I have witnessed the typical eBay sell prices of many pre-owned Rolex and Omega models essentially double. 
Bottom line – if you do your research and buy the right pre-owned model at a reasonable price, the value of your watch will inevitably increase.
Finally, I would like everyone to note that the above comments relating to value appreciation are really pertaining only to pre-owned watches.   Purchasing a new watch from a retailer certainly has its appeal in terms of warranty, condition, support, etc.  But a new watch is like a new car, or maybe even worse.  As soon as you leave the dealer, your new watch depreciates 25%.  With a new watch, you may possibly see some increased value after 10 or 20 years.  But a pre-owned watch may show appreciation in just 6-12 months in some cases.  Friend and relatives always come to me for advice about purchasing a watch, and I will always tell them to NOT buy a new watch.  Instead, I would strongly recommend buying a slightly used one on eBay from a reputable seller.



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