Perfect 3 Watch Collection

I’ve been in the luxury watch world on a business end since the early 2000s. In those early years I was exposed to just about every watch you could imagine, and would wear a different watch every few days. During that period in my life, I formed pretty strong opinions about which watches I did and did not like on a personal level.

Before I really got into the watch industry as a profession, I was a fanatic, just absorbing as much information as I could from watch magazines and early forums and sites. Unlike many, the first real watch I bought myself was an Omega.

Omega was affordable and to somebody in their early 20s a great masculine look. At the time I believed Rolex was a great watch, but not really affordable and not something that suited someone of my age. The first Omega I purchased was a Seamaster 300 GMT with a white dial. Like most, the first watch you gravitate towards is a diver. The Seamaster 300 is one of the five most well known divers, so easy choice.



Naturally not much time passed and I was already looking for the next watch. Now remember I was still young, living at home and not really making crazy money being an entry level software developer. I really did like my Seamaster and knew I’d have to give it up to get another watch. Around this time, Omega had just released their Seamaster Planet Ocean series, and they had to release one with an orange bezel. Having gone to the University of Texas, orange was my ingrained favorite color. So after selling my Seamaster GMT, I quickly ordered an Omega Seamaster Planet Ocean with an orange bezel.



Re-occurring theme here… after what was probably six months to a year, I started getting the itch to get rid of the Planet Ocean for something else. Around this time I was really deep into everything watches, and I was looking for something from a more old world respected watch manufacturer. I had a friend who was also really into watches, who had a little more financial might than I had, and his brand of choice was IWC. His watch of choice was the IWC GST Aquatimer 2000 (funny keep reading…), which was a bit out of my price range. When I started looking around, I stumbled upon the IWC GST Chronograph in Titanium. I once again sold my Omega and bought the IWC.



The GST Chronograph was a lot more affordable than the GST Aquatimer 2000, but had the same look and was made out of titanium, which gave the watch a distinctive look while being extremely light. It’s weird that nearly 20 years later, I would revisit the GST line (hint hint). I never really had any issues with the GST Chronograph, but this was also the time I was starting my career in the watch industry. With having access to literally any watch in the world to wear, the GST started sitting around. In short order I listed the GST for sale.

This now marked an extremely long period of time, roughly from 2005 until 2021 where I did not have a watch to my name. During this time I wore everything including from complicated Roger Dubuis, gold Ferrari Panerais, every Offshore under the sun, the first Richard Milles and literally everything in between.

A few watches stuck out during this time and made a lasting impression on me. First and foremost was the Audemars Piguet Royal Oak Offshore Juan Pablo Montoya. I had extensive time mostly with the titanium version, but did spend over a week in Vegas with the rose gold version for our wedding in 2008. Nothing like a 20 something wondering around the strip with a hundred thousand dollar watch on. Unlike today, nobody knew what these watches were, and I’d probably be more in danger wearing a steel rolex.

Another watch that really made a lasting mark on me was the IWC Big Pilot. I just loved everything about the watch. It was a super legible watch with probably one of the cleanest dial designs I’ve ever seen. The watch had an incredible 7 day power reserve and the textured buffalo strap really set it off. The Big Pilot was also the watch I wore when I got engaged to my wife in New York City. I remember the day after we got engaged having to rush to ship the watch out, because that exact watch sold the night before. Being such a fan of the Big Pilot, I even met up with John Mayer to potentially purchase his limited edition titanium Big Pilot perpetual calendar. I really didn’t have the ability to purchase the watch, but given his status in the watch world, having that watch with papers in his name would have been an amazing piece to own.



Now from around 2010 to 2021, I really didn’t care too much about watches. I’d been through the ups and downs of the business and was no longer around the physical watches. I worked remote and watches were just a job to me. I started getting my passion back for watches around the time all the YouTube content creators were starting to put out high quality videos about the business as well as the actual watches.

Having missed so many ups and downs with watch trends over the previous decade, I was still in the mindset of a late 2000s watch obsessed collector. Rolex was a brand that the entire catalog could be bought at a discount (minus the steel Daytona), Richard Mille was an up and comer that also sold at discount and I didn’t find too appealing, Patek made small dress watches and the Royal Oak was the less popular and boring older brother of the Offshore.

When I decided I wanted a watch of my own, I told the owner of the watch company I helped start all those years ago that I wanted to have watch of my own. He agreed and ended up sending an IWC Top Gun Chronograph 46mm in ceramic. This was a great watch, but here is where we start getting into the title of this article. As soon as the watch arrived, I had a constant thought in the back of my mind that this was not a Big Pilot. This little voice drove me nuts, and I knew I’d never truly be happy with this watch.



Around this time my wife got pregnant with our first children, twin girls. We were also transitioning out of our life in a small town west of Austin called Llano. We had moved from west Austin to Llano a few years prior, where we gut renovated both a 110 year old house and also an even older building on the city square which we turned into a brewpub. So much of our money was tied up in the house, business and now the upcoming twins, that it wasn’t really a great time to go out and buy a Big Pilot.

As seems to always happen in our life, I was able to figure it out and do some contracting software work for a friend who in return ended up agreeing to get me a Big Pilot. Now I pretty much had the choice of any Big Pilot. I had a natural love of the original steel 5002, but the newer titanium Heritage IW501004 was really calling to me. We found a near mint, complete set Big Pilot Heritage and in a few days it showed up. When the watch arrived, it was everything I thought it would be. For once I felt I had a watch I’d keep forever.



The one thing that drove me nuts about the watch, was it didn’t come on the original 5002’s buffalo leather strap. The original strap just had the rich color and texture that to me made the Big Pilot. After what seemed like weeks of searching, I found a dealer in Los Angeles that had a new original buffalo leather strap. Now combined with the Heritage, I now had the ultimate Big Pilot, or so I thought… The Heritage was never a watch I intended on selling and was even there when our daughters were born, but things change.

I now had the Pilots Chronograph Top Gun and the Big Pilot Heritage in my collection, and I thought I needed a divers watch. After some looking around I found a very good deal on an IWC Aquatimer IW356802. When the watch arrived, I loved the look of the sapphire bezel along with the black and yellow color scheme, but the watch really didn’t work for me. It wasn’t super comfortable and it was rather heavy.



So here I was, sitting with a three watch collection that didn’t really do much for me. Apart from the Big Pilot Heritage, the other two never got any love from me. I now decided it was a good idea to trade out these two watches on a ceramic Big Pilot. I started hitting up every dealer who had a Big Pilot in ceramic and really wasn’t getting anywhere. I really wanted the Big Pilot Top Gun, but ended up settling on a Big Pilot Miramar.



Now this was a watch that I instantly regretted buying as soon as it showed up. I’m not really sure what it was, but the watch never really did it for me. Maybe it was the polished ceramic that just grabbed every fingerprint, the mute dial or the fact that it wasn’t a Top Gun ceramic. Either way, I knew at some point it would go. Around this time I got the harebrained idea to try and trade the Big Pilot Heritage and Big Pilot Miramar on something a little more special, but more on that later.

Let’s switch up a little from the IWC train here for a bit. For nearly a decade, the watch that I have always wanted was the Audemars Piguet Royal Oak Offshore Juan Pablo Montoya in titanium. I had worn the watch numerous times over the years and even when compared with much more expensive Offshores, it was still my favorite. When I was heavily into watches, this was a forty to sixty thousand dollar watch during the limited offshore craze, something I thought I’d never be able to afford. Now with big watches not being as popular as they once were and now the Royal Oak being the desirable watch, the Montoyas were down in the 20 and 30 thousand dollar range depending on condition and if they were complete sets. We had even started up and little fund that had some money in there from little projects I had done that was going towards buying one. Also my wife mentioned if she sold some family property she’d buy one for me.

Once again, sometimes life works out weird for us and through helping a friend out, he ended up offering to purchase a Montoya for me. This came out of nowhere and literally blew me away. I even remember asking him on the phone “are you serious?” We were able to find a complete set from a reputable source and the watch was ordered. I remember tracking the flight the watch was on, which was delayed in Florida and thinking to myself, this watch isn’t mine until it shows up at the doorstep… something has to go wrong…

Nothing went wrong and the watch showed up. I remember opening it up and just feeling, ok I’ve done it, watch collection over. The watch just felt and looked just like I remembered, remember it had been over a decade since I’d seen or wore one. Now this is a watch I will keep forever, slot number one filled out for my 3 watch collection.



Ok back to the Big Pilots… Just like the Montoya, the Big Pilot Perpetual Calendar was one of those “I’ll never have the funds to buy one of these” watches. I knew it was a long shot, but I thought there had to be a dealer out there that would consider trading a Big Pilot Perpetual Calendar on a Big Pilot Heritage and Big Pilot Miramar. The market prices were pretty similar on this trade. I was also pretty picky, I wanted a black ceramic Big Pilot Perpetual and that really only meant two models, the Top Gun and the Rodeo Drive. To be honest, I really didn’t like the Rodeo Drive nearly as much. It had a 46mm case versus the 48mm case of the Top Gun and it also had a blue dial versus the black dial on the Top Gun.

Over the next few months I would contact any dealer who had a Big Pilot Perpetual Top Gun or Rodeo Drive in stock and just kept striking out. The closest I was getting, was both Big Pilots plus six to seven thousand dollars. One day when we were making our way back home from a weekend vacation, one dealer said he’d do the trade for a Top Gun Perpetual Calendar if I put up $1500. He seemed happy with the trade and having to put up that amount of money for a dream watch was fine with me. Although I was very sad to see the Big Pilot Heritage go, I knew the Top Gun perpetual would be a watch I’d keep forever, like the Montoya.



When the Big Pilot Perpetual Calendar Top Gun arrived, it became my daily watch of choice. The only change I made to it, was getting a new strap and spring bars from IWC. The watch didn’t need either, but I’d rather start clean with a watch of this caliber. The perpetual calendar is by far the most useful complication out there and on the large dial of the Top Gun (48mm), all the data is displayed extremely well laid out and easy to read. Also the perpetual calendar mechanism in the Big Pilot is so easy to set, there is really no reason to have it on a winder to avoid setting. The ceramic is pretty much scratch proof and wears very light, making it a perfect daily watch. Also the 7 day power reserve means I really don’t need to set the watch often. So along with the Montoya, I now have two slots filled up in my perfect three watch collection. One being the grail watch, in the Montoya, and the second being a tough as nails, goes with any outfit, high complication watch in the Top Gun Perpetual.

Since my wife really likes to travel, and I don’t feel comfortable traveling with five figure watches, I really needed another watch in my collection for those times when something a bit cheaper is called for. I had purchased a Sinn U2 for an extremely good price and thought this could be that watch, but after our first mini vacation with it, I knew it really wasn’t the right watch. I have gotten so used to the weight of ceramic and titanium watches, that a watch made out of submarine steel was just way too heavy for me. Although the Sinn U1 and U2 had been on my shortlist forever, in reality it just didn’t work out.



So I was looking for something in the four figure range, lightweight, good for vacations and that had some meaning to me. This criteria basically means a ceramic, carbon or titanium case and more than likely a diver on a rubber strap. I’d had a few more recent IWC Aqautimers and they really didn’t do it for me, then there was some Ulysse Nardin divers as well as the Blancpain Fifty Fathoms. Around the time I was looking, there weren’t any good deals on either of those. For fun, I thought I’d look at what the old IWC GST Aquatimer 2000s in titanium were going for. As I thought, there were not many on the market, with most being from Japan with not enough links to fit my wrist. I did find one listing for a GST Aquatimer 2000 in titanium for a great price in New York. The pictures were terrible and the watch looked rough. After speaking with the dealer, he told me he used to be an Authorized Dealer for IWC and he sold this watch to a client in the early 2000s and ended up with the watch again after all that time with the original owner.

The watch had all of its links and was a complete set. Even with the terrible pictures and how rough the watch looked, I decided to give it a try. When the watch arrived, it just needed a cleaning with warm water and soap to look factory fresh again. I do not care for bracelets and I was able to get the rubber strap and buckle from the next generation Aquatimer that fit the GST Aquatimer 2000. On a rubber strap, the GST Aquatimer is near perfect for what I wanted. A super lightweight titanium watch, water resistant to 2000 meters and didn’t break the bank. The watch was running extremely bad on my timegrapher when I first got it, but got within 1 second a day after running for a few days. This watch was also the first real pure IWC diving watch, after the Porsche Design Ocean 2000, and being such a fan of IWC means something to me. It's also fun revisiting my first real luxury watch, which was another watch in the IWC GST range.



So there you have it, my “perfect” 3 watch collection. I could probably trade all three and get something crazy, but in all honesty I don’t even see a watch I’d do that for. Even something like a crazy Richard Mille wouldn’t entice me, not to mention my collection wouldn’t even be in the same ball park value wise. The Montoya is a grail watch, the Top Gun Perpetual fills my love of the Big Pilot and is probably the best Big Pilot available… and the GST Aquatimer 2000 is probably the best “beater” watch I can think of.

The watch of the three I could possibly see myself trading is the GST Aquatimer 2000, but it would be for something crazy like the Blancpain Fifty Fathoms Tech Gombessa. The problem with doing that is then I’d have another five figure watch that I’d be nervous to lose / travel with. So for all intensive purposes, this is my watch collection. While I do have other watches, they are not watches I really wear and just don’t sell for one reason or another.

Now if you’re still here… thanks means a lot and hopefully you are starting to understand my strange life in the world of watches. Let’s do something fun here as well. Let’s talk about my wife’s collection, and possibly figure out a third watch for her collection!

My wife got interested in watches naturally because I was. I had bought her many watches over the years, but nothing truly substantial. The first real watch she got was a Glashutte Original Sport Evolution M in steel. Glashutte Original is a truly underrated brand that makes some amazing timepieces, the watch just never resonated with her. When she bought her second watch, the Sport Evolution M received zero wear time, meaning it would soon be sold.



Although I’m not a big fan of Rolex, my wife has always appreciated them. We both knew that she enjoyed larger watches, so we really had to look at the sports models. This basically limited us to Submariners, GMTs, Daytonas, Yacht-Masters and Explorers. The Subs, Explorers and GMTs were just too masculine and the Daytona, mid hype, was just way too much money for what it is. This left us with the Yacht-Master.

The Yacht-Master 16622 quickly jumped to the top of the list. This model was designed to be the replacement to the Submariner, but given how popular the Submariner is, was decided to become its own series. The 16622 is a steel watch with a steel bracelet and platinum bezel and dial. The case is borrowed from the Daytona with rounder more feminine curves and polished center links, giving the watch a more dress like appearance. The textured platinum dial also gives off an amazing play of light when the sun hits it. We were able to get the 16622 from the watch company I helped start at an amazing price, so it was an easy choice to go with.



My wife was very happy with the Yacht-Master and would probably just be fine having it alone. With an upcoming cruise, I really wanted her to have something that wasn’t a Rolex to take on vacation. I was thinking that the Glashutte Original on a rubber strap would be fine for the trip, but then something else came up. Although Hublot is universally hated on by watch snobs, my wife and I still think they are a great brand with a bad rep. I am always on the lookout for Hublot Big Bangs at good prices to resell, and out of nowhere a Big Bang All Black popped up, which I was able to pick up at an amazing price. In the back of my mind, I thought this would be a great watch for my wife and replace the Glashutte Original. The watch was also half the price of her Yacht-Master, so it would be a great vacation watch.



When the watch arrived, my wife wore it to dinner and was in love. The watch is crafted in black ceramic, with a black dial, black mirrored hands and black rubber strap. Being ceramic the watch is very hard to scratch, my wife isn’t the most gentle with her watches, so this is great. It is also very light and on rubber is great in warm weather and water. With most Big Bangs being 44mm and larger, this 41mm All Back wears perfectly on her wrist. Also with how inexpensive it was, when/if the Hublot hate goes away, this watch should appreciate quickly in value.

So now my wife has a very solid two watch collection, which she wears equally. In reality, she doesn’t need or want a third watch, it’s more me feeling like she should have something else. We both really do not dress up with Austin being such a laid back city. The Yacht-Master pretty much covers most dress situations and both it and the Big Bang can be worn with pretty much anything.

If I was to pick a watch for her, it would probably be from either of my favorite brands, IWC or Audemars Piguet. IWC really doesn’t have anything that I think she would really enjoy, more than likely just getting a smaller pilot for the sake of just having an IWC. Now Audemars Piguet does have a great line up of Royal Oak Offshores for women. I’m talking more about the older models from the 2000s with diamond bezels. Prices seem to be up a bit right now on these, but who knows maybe something will pop up.



So there you have it, my perfect 3 watch collection, and what I believe to by my wife’s perfect 3 watch collection. I look at watches all day long and don’t even feel the slightest desire to add another watch to my collection, so I believe I’ve almost achieved watch collection nirvana.