Preppy Men’s Watches for 2019

Having a quality collection of preppy men’s watches is an investment in your future success. It can make a statement about your quality as a man and open doors that you never knew existed. Not to mention, its also very cool and a great improvement to your style if you know what to buy. 

Not sure where to start? No worries, I am here to help and this article will guide you to the perfect watch collection to match your preppy style.

As a preppy myself, I know how limited our choices are when it comes to cool watches to wear with your Polo sweater or Vineyard Vines tee.  The watch needs to make a clear statement.  “I’m fun”.

On the other hand, when in the office, your preppy watch needs to make a very different statement.  You need to be perceived as reliable and conservative.  The cool preppy men’s watches you have for the beach will never be acceptable in the office.  This is why every prep-ster needs at least 3 watches.  We need to have one for the office, one for casual everyday wear, and one for fun.

Remember 3 is the minimal, more the better.  I have 10 and I often feel I need more.  Good news, I can show you some tricks to get a lot more wear from your current watch collection and save you a boat load of money (so you can put that extra cash for sailing with Buffy in the sound!).

Preppy Men’s Watch Buying Advice

There is a lot of junk out there and preppies only buy quality.  We know that quality will last a lot longer and therefor be way cheaper in the long run.  Quality doesn’t have to mean expensive, but often times it is.

I am always looking on Amazon for a new watch and I find a lot that look really nice.  When I research the watch I always look at these 4 critical areas that define watch quality.

  1. Where was the watch made?
  2. What movement is in the watch?
  3. What is the crystal made from?
  4. Is it a quality name brand I can trust?

These 4 things will tell me if the watch is a quality timepiece or a piece of junk to be avoided.  I am sorry to report, the large majority of watches I found on Amazon failed all 4 of my tests.

Where was the Watch Made?

I will only buy a watch if it is made either in Swisserland or Japan.  The watches I see mostly today are Chinese junk and need to be avoided at all costs.

The brand will often tell us where the watch was made.  I love mostly Swiss made watches but you can never go wrong with a well known Japanese watch like Seiko or Citizen.  They are well known for their quartz movements and reliability.

Japanese Watches

Watches like Orient, Seiko, Citizen, and Casio are all made in Japan and are high quality watches.  These tend to be lower cost watches compared to their Swiss counterparts but will last a very long time if taken care of.  I have a $25 Casio in my collection that looks like a $300 watch and I wear it with my preppy office outfits all the time.  Very classic styling and goes to show you that great preppy men’s watches don’t need to cost a fortune.

I have one Seiko watch that belonged to my grandfather still in my collection.  I rarely wear it because I think it looks too small on my wrist but I love knowing its been in my family for so many years.  I look forward to handing it down to my kids when the time is right.

I personally think the best quartz watches are made in Japan and you should have at least 1 in your collection. Preferably by Seiko since they invented the first quartz watch in 1969.

Swiss Watches

There is little doubt that Swiss made watches are the best in the world.  Swiss watches are made with surgical grade steel for their gears and pins.  They are often assembled by hand and are easily serviceable by a good watch maker.  Lastly, they are often made with a high end sapphire crystal which is the best type of crystal you can get in a watch.  In short, they are built to last.

Swiss watch making is an art and very serious business in Swisserland.  They take great pride in making quality watches and you can easily tell the difference when you handle them.  They are hand assembled and inspected, and highly respected in the watch wearing community.

There are too many great Swiss made brands to list here but here are just a few I own (in bold)  and can highly recommend.  Good brands to look for are Tag Heuer, Omega, Wagner, Victorinox, Invicta, Tissot, and Hamilton.

Preppy men’s watches are often made in Swisserland and include luxury brands like Rolex, TAG Heuer, Carrera, Omega, Tudor, Breitling, Zenith, IWC, Hublot, Bell & Ross, Victorinox, Raymond Weil, and Tudor.  You rarely find these for under $1,000 but if you do (and the watch fits your style), buy it.  Just make sure its real!

Watch Movement

The movement for a watch is like the engine in a car.  This is way more important then all the other parts combined.  Never cheap out and buy a cheap movement.  If you don’t know where the movement was made, pass on the watch  If it’s a quality movement, they will tell you!

There are 3 main types.  You have the standard Quartz movement, Manual, and the Automatic movement.  The automatic movement comes is self winding.

Manual watches usually require winding every day.  Automatic self winding watches are typically watches that wind themselves and do not take a battery.  Automatic watches can also be wound manually so you can make sure your watch is always powered and keeping good time  I also recommend a winder case for your high-end automatic watches to make sure they are ready to go when you put one on.

Watch Crystals

The crystal is the glass covering the watch face and can be made from 3 different materials; Plastic, Glass, and Sapphire.  Watch makers are constantly finding new ways to improve upon crystals and you will find a lot of hybrids of these 3 main materials.


Plastic is the cheapest and is very prone to scratching.  This is a clear sign of a cheaply made watch and should be avoided. A light tap in the glass will confirm the difference between plastic and glass/Sapphire.


The next grade up are glass crystals.  There are many different hybrid glass crystals like mineral glass, Sapphlex, Gorilla glass, and Hardlex to name a few.  Watch makers are working to improve the quality of glass crystals to make them more scratch resistant and are succeeding.  I own several mineral glass watches and am very happy with how the crystals hold up with my active lifestyle.


The top of the line are sapphire crystals.  There are 2 main types, natural and synthetic, and both are highly recommended.  Synthetic is just man made sapphire and is the most common sapphire crystal.  Sapphire crystals are the best and belongs in all preppy men’s watches.

Ways to Avoid CHEAP Watches

I am a big fan of several man’s style YouTube channels. The Modest Man is one of them and in this video, Brock talks about how to find and avoid cheap watches and follows a very similar approach to mine. Give it a view and see if you agree.

The Modest Man – What to look for when buying a watch

Quality Name Brand Preppy Watches

Watches have always been more about style then telling time.  Men have so few accessories that selecting the right watch is critical.

To select the right preppy men’s watch, you need to consider its brand.  We talked about the quality brands above and talked about great Japanese and Swiss companies that make the best watches.  If you stick to these brands, you will never go wrong.

Brands can be divided into different categories. 

They can be Consumer, Enthusiast, and different levels of Luxury brands.  Prices are all over the board but expect to pay several hundreds to several thousands for a quality watch from this list.  Any Swiss or Japanese watch on this list is recommended and they will be clearly marked on the watch face or back.  Only watches made in Switzerland will be marked “Swiss Made”.  Be careful of other wordings (like “Swiss Quality”) which is not a Swiss made watch.

Here is a list of recommended quality watch brands that broadly range in prices from around $20 to 50K+.  Follow the guide above and look for the 4 key traits of a quality preppy men’s watch and you will not go wrong. There are links to each companies website and to their wiki page for more information about the brand and their watches.

Recommended Watch Brands



Quasi Luxury

Timex – Wikipedia
HMT – Wikipedia
Fossil – Wikipedia
Swatch – Wikipedia
Stuhrling – Wikipedia
Tianjin SeaGull – Wikipedia
Seiko – Wikipedia
Invicta – Wikipedia
Swiss Legend 
Guess – Wikipedia
Nixon –  Wikipedia
Rotary –  Wikipedia
Citizen –  Wikipedia
Orient – Wikipedia
Casio –  Wikipedia
Skagen –  Wikipedia
Vostok –  Wikipedia
Bulova – Wikipedia
Diesel – Wikipedia
Mondaine – Wikipedia
Benrus –  Wikipedia

Michael Kors – Wikipedia
Marathon – Wikipedia
Certina – Wikipedia
Suunto – Wikipedia
Luminox – Wikipedia
Tissot – Wikipedia
Stowa – Wikipedia
Hamilton  – Wikipedia
Christopher Ward  – Wikipedia
Gucci – Wikipedia
Movado – Wikipedia
Mido – Wikipedia
Rado  – Wikipedia
Longines  – Wikipedia
Raymond Weil – Wikipedia
Oris – Wikipedia
Tutima – Wikipedia
Sinn — Wikipedia
Fortis – Wikipedia
Junghans –  – Wikipedia

Entry-level Luxury


High-end & Ultra Luxury

Baume & Mercier – Wikipedia
Hermes – Wikipedia
Nomos Glashütte – Wikipedia
TAG Heuer  – Wikipedia
Ebel – Wikipedia
Doxa – Wikipedia
Tudor – Wikipedia
Bell & Ross – Wikipedia
Ball – Wikipedia
Montblanc – Wikipedia
IWC  – Wikipedia
Omega – Wikipedia
Grand Seiko
Bvlgari – Wikipedia
Breitling – Wikipedia
Chronoswiss – Wikipedia
Bremont – Wikipedia
Zenith – Wikipedia
Hublot  – Wikipedia
Cartier – Wikipedia
Panerai – Wikipedia
Rolex – Wikipedia
Jaeger-LeCoultre  – Wikipedia
Chopard – Wikipedia
Ulysse Nardin – Wikipedia
Breguet – Wikipedia
Girard-Perregaux – Wikipedia
Blancpain  – Wikipedia
Glashütte Original  – Wikipedia
Breguet – Wikipedia
A. Lange & Söhne –Wikipedia
Piaget – Wikipedia
Audemars Piguet –Wikipedia
Patek Philippe –  Wikipedia
Vacheron Constantin – Wikipedia
Richard Mille – Wikipedia
MB&F – Wikipedia

Style Rules and Other Things to Look for in a Preppy Men’s Watch

Since preppy men are often near water, our watches need to be waterproof.  We never wear digital watches and these should be avoided unless you are a runner and need the stopwatch.  There is little preppy style in digital watches except for the smart watches which I think are interesting.

We also avoid watch trends and tend to stick to classic styling.  I will go for a classic diver style or a luxury dress watch with a brown or black leather band. We also like to get a little wild with color and have watches with a colorful canvas strap.  Remember to always match your watch band to your accessories. 

The basic rule is to match your leathers and metals from your head to your foot.  Leather watch bands match your belt and shoes.  I even go as far to make sure my leather watch band also matches my leather jacket.  Go big or go home!

Every man needs at least one Luxury automatic watch.  Make sure the brand is the best quality you can afford.  I never recommend buying anything you cannot afford.  You will be able to upgrade in time and you should never need to borrow money to buy a watch.  If you cannot afford a $1,000+ watch today, then but a $100 automatic and plan to upgrade down the road.

Preppy Men’s Watch Collection

Every man needs several watches to cover their different lifestyles.  We have our professional life, casual life, and our weekend party life.  Most of the time, one watch will not cover all these different elements of style so we will need at least 3 watches in our collection.  Most modern gentlemen have way more.  Personally, around 10 is probably best suited for a preppy man’s watch collection today.

The watches preppy men wear are expected to last a lifetime so we can afford to spend a little more for quality.  Quality does not mean trendy and most of the watches being marketed today are poorly made in China and will not last more then a few years.  Buy reputable brands and demand quality.

I found this great video by “The Kavalier” on how easy it was for him to design a watch and start his own watch company.  The important takeaway here is the cost to build and ship the watch to him is under $5 (in quantity).  I often see these watches sell for well over $50 to $100.  I can promise you there is no quality in a $5 watch. Buy the best.

Why “Watch Guys” Hate Fashion Watches

Let’s cover the basics and the 3 types of watches you should have in your collection.

Preppy Men's Watch
Hamilton ‘Jazzmaster’

The Classic Professional Watch

Every stylish man knows when he get’s dressed every morning, the unbreakable rule will always be, all your leathers need to match!

When dressing for the office, you are likely wearing leather shoes and a belt.  It should go without saying those should match perfectly.  You must also extend this to your watch band.

When in the office, if you are wearing black shoes, then your belt and watch need to also be black leather.  Same with any other color like brown and tan.

Preppy Men's Watch
Tissot Tradition

The good news here is you don’t need a different watch for every pair of shoes you own.  All you need are several sets of quick release high quality leather bands (more on this later).  You also need some high end watches to go with these bands.

The vintage Rolex is the king of Preppy men’s watches. 

Its classic but simple, gold face and dial look fantastic in brown or black leather bands.  The good news is your don’t need to buy a $20,000 Rolex to get this look.

Seiko Eco Drive

Citizen Eco Drive

This classic style is extremely popular and available by many manufacture.  This design is available from Casio, Timex, Seiko, all the way up to a Hamilton or an Omega Sea Master (My dream watch).

This is the first watch you should buy for the start of your collection. With a entry price of around $50-100 for a good quality Seiko Eco Drive, it will not break the bank either.

The Casual Watch

Preppy Men's Watch
Tag Heuer ‘Formula 1’

This is the watch you wear on casual Friday’s and on weekends.  I would go for a quality stainless steel diver watch. I recommend a Seiko or Orient and are fantastic. These start at around $100 but you can always get a deal for maybe 1/2 that if you look hard..  If you can afford a more expensive watch, then upgrade to a Swiss made Tag Heuer or Breitling.

Preppy Men's Watch
Seiko 5 Black Dial Stainless Steel Automatic

Remember these are lifetime investments so calculate that into your costs for what you can afford.  If you can save $200 a year for just 5 years, you can afford 1 of these beautiful Swiss gems.  I tend to buy my high end watches used from a local jewelry store that I trust and save a fortune in the process.

For example, I bought my Tag for around $800 and my Locman for around $600.  Both these watches retail for over $4,000 when new. Take your time and find something you love at a great price. You will never be sorry for buying a quality watch at a great price.

Preppy Men's Watch
Citizen Eco-Drive

The Fun Preppy Men’s Watch

This is the type of watch most people relate to a preppy wardrobe.  These watches are the ones with canvas bands, bright colors, and trendy styles. 

Given its nature of being a fun watch, it will tend to get beat up while you are out and about.  I recommend a very durable watch with interchangeable bands to give you lots of options when coordinating with your other accessories and shoes.

Preppy Men's Watch
Timex Unisex Weekender

I have two Timex watches that I use in this category.  The watch is not durable but often has the right look I am going for. These cost around $25 for each.  I am ready to replace these with a higher quality Wegner, Citizen, or Seiko at the first crystal scratch, but until then, I will enjoy them every chance I get.

For the record, I have already bought the Wenger replacement and still wear the Timex Weekenders often. I guess its somewhat true, they take a licking and keep ticking (so far for me, 12 months and not a single problem or scratch).

Replacement Bands

Preppy Men's Watch
Wenger Analog Swiss Quartz Green Watch

This is where those quick release or Nato style bands will come in handy.  It will be a snap to change the look of just about any watch for just a few dollars a strap and dramatically increase its function in your wardrobe.

Smart Watches

This is not one of the 3 required watches but I wanted to throw it in to cover the new possibilities this watch can have in preppy men’s watch style. 

I wear both an analog watch and a fitbit and I am not crazy about the look and inconvenience of always wearing both.  A smart watch could serve both functions and provide a load of extra function to my life.

If you are a Prepster (like me), your life is surrounded with technology.  In my case, I tend to really want to hold on to the old lifestyle look.  I love leather books, simple cars, and dark wood in my home study.

Smart watches take away the simple lifestyle I really like. But sometimes we must evolve and change.  This is why I am wondering if its time for me to adopt a smart watch into my watch collection.

I will never give up my traditional watch collection and smart watches will only work in my lifestyle if it can seamlessly fit into my lifestyle. Only time will tell.

Watch Accessories

There are few things that truly revolutionize an industry.  In my opinion, the quick release watch band are one of these things that will bring new life into your collection and I cannot recommend them enough.

Being able to quickly swap out your watch band and reuse your watch case to completely change the look is a feature you cannot live without.  This will allow you to reduce your collection to a single watch if you really want and just swap bands to meet the 3 core needs of a modern gentlemen today (Professional, Casual, and Fun).

Quick Release Watch Bands

Barton Quick Release – Top Grain Leather Watch Band

Burton is leading the charge in quick release bands and charges a reasonable price (around $20 per band) for a very high quality watch strap.  You can save some money and go with Chinese ones for less but I recommend spending just a little more and getting quality.

Your band collection should contain several leather straps to match your belts and shoes (Black, Brown, and Tan).  You should also have some canvas and nylon Nato straps to introduce lots of color into your collection.  These extra straps will cost you well under $100 and multiply your watch wearing options.  Completely worth it!

Watch Case

BARTON Watch Bands – Choice of Color

The other things I recommend is a watch box.  I recommend every gentlemen have at least one automatic watch and a winder will keep the watch wound and ready to wear.  It is also much better for an automatic watch to keep the gears moving.

Automatic Watch Winder Box

I bought my 10 watch winder case on eBay for around $60 and the motors lasted about a year.  Very disappointed in the Chinese crap but I wasn’t able to find anything I knew was quality for an affordable price. 

I will likely buy a replacement soon because there are really no other options.  I am waiting for a winder to be available with a USB charging option inside so I can charge my smart watch and wind my automatics.  Maybe I will build one and sell it on Amazon for a good price.


Preppy men are all about classic styling.  Preppy men are also all about having fun.  You watch collection must fit both needs and easily can.

I understand that watch wearing is becoming a lost art in preppy men’s style.  With the time easily displayed on everyone phones these days, it’s no longer needed to remind you about things on your schedule.  Watches are no longer needed as a way to tell time, they are critically needed as a way to hold on to our traditions and values.

We need to remember to slow down and take time for the things that are important to us. 

More then 1/2 of my watches in my collections were gifts from my wife that we bought together for special occasions.  I value them for what they mean to us.  They are reminders of our life together and remind me to always look for ways to spend more quality time together.

I always think a nice watch is a fantastic gift for any gentlemen and I have given several to family members.  I can only hope they also value them in the same way I do and hope it reminds them of all the good times we had together.

If you need a gift idea for someone special in your life.  How about watch shopping in the vintage watch shop in your town.  The experience will be time well spent.