Advice for Buying a Watch

Advice for Buying a Watch

The Watches of Espionage community can be broken down into two segments: professional watch nerds tired of the traditional watch media; and complete newbies, those initially attracted by Military and Intelligence content but with little interest in watches.  Over time, the latter group usually develops an interest in watches and regularly asks where to begin.  

This Dispatch is for you, newbies.  It’s a cheat sheet for breaking into the world of watches. Our goal is simple: to cultivate and preserve watch culture in the NatSec community.  We have no commercial relationships with any of the brands mentioned, and we’re brand-agnostic.

Seiko Watches of Espionage
(James Rupley)

Step 1: Do your research:  There are more resources than ever on watches, and if you are reading this then you’ve already demonstrated that you’re far enough down the rabbit hole and you want to know more. 

We at W.O.E. do not do traditional watch reviews- but other platforms do and do it well.  Hodinkee, Bark and Jack, Teddy Baldassarre, Fratello, aBlogtoWatch, etc.  There are plenty of great outlets with different perspectives putting out content on Youtube, online editorial platforms, and podcasts.

But it’s important to exercise caution when it comes to any enthusiast media, as much of the content on these sites are paid advertisements and/or heavily influenced by the watch brands.  Read our Covert Influence In Watch Media piece so that you approach it with a skeptical eye.

Moon Swatch

Step 2:  Talk with people. The simple lost art of conversation.  Ask your friends, coworkers and family members about their watches.  See a guy with an interesting watch on at a bar, coffee shop, or even at the urinal? Ask him what he is wearing.  Why did he buy that specific watch?  What does he like and dislike about it?  Ask to try it on. Most people into watches want nothing more than to talk about them.

Major cities likely have watch meetups. RedBar Group is the largest and most well-known of these group meet ups.  I have never been to a watch meet up but know a lot of people enjoy this community and it is a great way to get your hands on lots of watches in the wild.

Step 3:  Visit an AD.  An “Authorized Dealer” is a store that sells watches from major brands, and they have an official relationship with said brands.  We recommend visiting a dealer with a larger selection of brands so that you can physically try on different watches to see what works for you.  Tourneau, Watches of Switzerland, and Bucherer are some of the largest ones, but chances are even your local mall has a store that sells watches.

Sales associates can be notoriously pretentious and they’re not always “watch guys” but there is something to be learned from everyone.  At a minimum they should have the training to explain the range on the market.

Bucherer Geneva

Step 4:  Buy your first watch.  After spending a few weeks/months on steps 1-3, you should have a general idea of what interests you.  It’s time to buy your first watch.

Regardless of one's socioeconomic status and access to disposable income, we recommend starting with a watch under-$1,000, and even under $500 is better.  Just because you can afford a Rolex doesn't mean you should start there.  Check out our previous Dispatch on “Best watches under $1,000” for some thoughts from a broad range of practitioners with experience.

Arabic Seiko Watches of Espionage
(James Rupley)

Step 5:  Pause - wear your watch, repeat steps 1-3.  It’s tempting to immediately focus on the next watch, always wanting more.  But wear your watch, find out what you like/dislike about it. Sometimes you learn things about your taste only after wearing a watch for a while. Think about how it feels on your wrist, how it works with your lifestyle, etc. Most importantly, however, is to make sure that the watch works as an extension of your own life philosophy. Maybe the values of the brand don’t line up with your own–or maybe they do. This is the time to learn.

Watches of Espionage Travel Pouch Strap
(James Rupley)

Step 6: Accessorize.  A strap is a great way to change up the feel of your watch.  We have a host of straps in the W.O.E. shop, but don’t let us limit your options.  

In the strap game, you generally get what you pay for. Like most things in life.  Stay away from Amazon and pay a few extra dollars for something of quality.  Most of the major watch content outlets also sell straps and are a good one-stop-shop.  Buying a strap from a smaller business is a great way to show your support and rep that brand/community. 

Here are some of the different straps you should consider:

2 Piece Leather: These should be handmade in the USA or Europe, nothing mass produced. There are some great craftsmen out there making one off and small batch straps like our Jedburgh and Leather and Canvas DNC Strap.  A good leather strap can work on mostly any watch.

Affordable Nylon:  You can buy these anywhere and should be somewhere in the $20-40 price range.  Our Five Eye is on the higher end of this but in return you get quality. The better ones are well-made but cheap enough that you can use and abuse them and throw them out like a pair of good socks.  A simple nylon strap is a great way to support a group/person that you’re interested in.

Watches of Espionage Five Eye
(James Rupley)

High-End Fabric Strap:  In my opinion, Zulu Alpha is the best quality fabric strap on the market. The Quantum Watch Strap from TAD has great hardware and Tudor has some great fabric straps (see Hodinkee video). None of these are cheap but you get what you pay for.

Single piece leather is tricky, most are thick and I do not like to use bent spring bars on my watches. These do fit some of my pieces with a wider gap between the spring bar and I wear them. I am a big fan of both Soturi and Zanes.

Rubber: I have owned a few from Everest and overall have been happy with them. There are plenty of options on the market here and quality generally coincides with price.

Elastic MN Straps: I have a MN strap from NDC straps which I like and have heard great things about Erika’s Originals.  A great way to change up your watch.

A new strap can completely change the feel of your watch.  Most watches are 20 mm or 22 mm so if you buy a handful of straps you can rotate them between your watches.

Watches of Espionage Five Eye
(Photo Credit:

General Advice & Tips:

As you look to expand your collection, here are some general tips that we use as a north star.  Remember, none of these are hard and fast rules:

  1. Buy what makes you happy; no one else cares what you are wearing and 99.9% of people will not notice the watch you have on your wrist. (This one is cliché but it’s entirely true.)

  2. Buy the watch you can afford. You won't be happy if you spend more than you can afford.  “Buyer’s remorse” is real and can undermine the sense of satisfaction from wearing the watch.  DO NOT FINANCE YOUR WATCH.

  3. Don't buy for investment. Your watch may appreciate in value, but buy with the expectation you will wear it until you die (and a loved one will wear it after you die). Values are generally trending downward in the watch world anyway. That’s not what they’re made for, and treating a watch like a financial instrument takes away something from the passion.

  4. When in doubt, stick with a known brand: Seiko, Sinn, Rolex, Breitling, Omega, Tudor, JLC, IWC, Bremont, Patek, etc.  There are some great micro brands out there (like Tornek-Rayville, Sangin Instruments, Elliot Brown etc), but also a lot with smoke and mirrors, especially in the “tactical” space. Rome wasn’t built in a day. Any worthwhile watch company wasn’t either.  When you do decide to go into the micro-brand space, do your homework.

  5. Buy the seller and build a relationship with that person. If the deal looks too good to be true, it probably is.  A lot of people have had great experiences with Ebay and other online forums, but there is something about building a relationship with the actual person selling the watch that makes it special. Plus, it’s very easy to get burned on Ebay. It’s less easy to get burned by someone you know and trust.

  6. Take your time. Do your research. Even if you have the money to buy the watch you want right away, spend time learning about the different variations and history of the reference or brand. This will likely change your outlook and make you appreciate the watch you end up with even more.
IWC Mark XVII CIA Africa Division Challenge Coin
(James Rupley)

As a closing remark, don't feel like you need a "luxury watch," a ~$500 watch can be just as meaningful as a $5,000 watch. Remember, those Speedmasters that went to the moon and the 1675 GMT-Master examples that our pilot heroes wore were all value buys back in the day. They weren’t luxury products in that period.  As we have said many times, the man makes the watch, not the other way around.

Vintage Watches:

Lastly, if you are just starting out, we recommend staying away from vintage watches.  While there are some great deals out there and it is a lot of fun, it is not for the uninitiated.  There are plenty of fakes at every level and it is easy to get ripped off if you don’t know exactly what you’re doing.  Additionally, old watches come with old problems, this can be exciting once you have a handful of watches in your collection, but sending your sole watch off for service for 3 months doesn’t make for a good time. 

Happy hunting,


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Blackwater Breitling


Two thoughts, as a retired LEO I would never let a stranger try on my watch, they are very likely faster than me and if I did catch them my watch would likely get scratched in the struggle.
For micro brands try Resco Instruments. Great quality and customer service second to none.

Ben Chapman

I love every bit of this article. I build more watches than I buy, and sell plenty of homage builds for customers. People who know what they like and what they’re looking for are a joy to build for! I also love a tool watch, and a non-pretentious watch is always sexy. Only watch I think I would buy that’s expensive would be a Speedy just because I’m a space nerd!

Clark Stewart - Yellowhammer Watch Works

Sensible and ethical — what I’ve come to expect from Mr WoE.

Here’s my favorite piece from the above:

“Buy what makes you happy; no one else cares what you are wearing and 99.9% of people will not notice the watch you have on your wrist. (This one is cliché but it’s entirely true.)” (Source: W.o.E)

For watch enthusiasts and collectors, this astute observation is often a tough pill to swallow. Much like coin and firearm collectors, some in the watch community imagine others instantly recognize the watch brand they’re sporting on their wrists. (I might add here that the strap often garners more attention than the watch.) 😁

Thank you for sharing your knowledge/wisdom with us free of charge without subscription or paywall. I know I’ll forward this essay to family and friends.


Pat Sonti

Very well said! Most of my collection ranges in the $500-700 range, with several pieces belonging to relatives that have long since passed. These mean more to me than anything out of the Rolex catalog. Of the watches I have actually purchased myself, my most treasured is a simple titanium quartz field watch from Bertucci. Why? Because it’s accompanied me on adventures across the globe. That’s the beauty of watches, above all else they are tangible reminders of the passage of time, and the experiences we have as a result.

Tyler Rich

Excellent advice! Especially the point about affordability. Following the WoE advice of use your tools, buy a watch that you won’t mind getting banged around. Those scars will make the watch your own.
Well done, mate!

JR Seeger

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