The Top 5 Watches I Regret Selling, Or Not Buying — Rolex, Tudor, And Omega

Usually, around this time of the year, you look back at the year that (almost) lies behind you. Due to the current situation, there isn’t much to look back at or I simply just want to forget about it as soon as possible. And while thinking about it and translating that feeling to watches, something else came to mind. Sometimes you sell a watch and many years later you think, “why?” So here’s my list of watches I (sort of) regret selling or not buying.

When it comes to watches I’ve always been pretty straightforward. Either I love it or hate it, or as Rob likes to call it I find one naughty or nice. Looking at where my watch adventure started back in the days, the focus has really been rather narrow-minded. How much I wanted to own a Daytona, the funds lacked in my early twenties. So my first mechanical watch was a Rolex Submariner 5513 from1966.

Never look back

At first, I was extremely pleased with this watch and have worn it for quite some years. Realizing you have a nearly 40-year-old watch on the wrist which runs incredibly precise, almost like new, made me more curious about the technical side. That’s when I started diving more into the technical side of watches and this is where my watch journey actually started. By doing so I also realized that this Submariner was heavily polished and had several replacement parts. And although these were all original, the point came where I wanted a more time correct watch.

In the following years, I’ve bought quite a few watches and some of them were sold again. Looking back now there are a few which I actually should have kept. Either to have a bit more variation in the watch collection or simply because they are now at a price level that makes them impossible to buy again. On the other hand, I always say that you buy or sell something for a reason.

Rolex GMT-Master 16710

This is one of the watches that I both love and hate. It has always been the most versatile watch in my book as it looks amazing in all the various configurations. And this is also where the hate for this watch comes from. Through the years, I’ve owned several different versions of this GMT. Every time I bought a new one, it felt like a completely different watch on my wrist. That was okay for a while, but sooner or later, I got bored with it and sold again.

I’d be totally fine without it until I saw one on the wrist of someone again and started looking for a new one again. Through the years I’ve had various 1675 models, including one rare bird with an all-red hand and radial dial. But if I could turn back the clock, I would have kept the last 16710 I owned. It was the perfect balance for me. I find the more vintage pieces too delicate to wear in on a daily basis, especially when they are in pristine condition. The last 16710 to leave my collection was the Goldilocks GMT for me.

As soon as prices left 10K in the rearview, I realized that it’s not likely that I will ever buy one again. Back in the day, the price for one of these bad boys was around three thousand Euros. I could live with that. Somehow the artificial scarcity doesn’t justify paying North of ten thousand nowadays for the same watch. Even though the price will probably only increase, it still doesn’t make sense to buy a Rolex GMT-Master II at a price that the watch is just not worth. 

Rolex Daytona 16520

There was a moment in life where I had two Rolex Daytona watches in my collection. At some point, I had to make a decision about which to keep. While I loved the 16520 with Zenith movement more due to the white dial and contrasting black rings around sub-dials, it was missing its box and papers, even though it was a relatively young watch back at the time. This made me decide to keep my Daytona 116520 which came with the in-house movement and was a complete set.

Due to the lack of the box and papers, the Zenith Daytona was even hard to sell and it took me quite some time to find a buyer for it. At the time, this strengthened my views that I made the right decision. In the end, you don’t wear the box or papers but for a watch that isn’t too old, I still think it should be a complete set. Especially with seemingly endless growing prices, having a complete set is definitely a plus. On the other hand, watches are made to be worn and I still think the Zenith looks better. Since I had the dial of the white gold Daytona installed in my 116520 it completely changed the look for the better.

Tudor Submariner 7928

Many years ago I bought a Tudor Submariner 7928 from a Belgium watch friend. Originally, he’d been hoping to sell me a Snowflake. As such, he drove all the way to my place with a Snowflake and brought the Submariner along for the ride. While the Snowflake didn’t do it for me, the Sub definitely did.

Sadly it wasn’t for sale (at the time). After apologizing for him driving to Holland without doing a sale, both watches (and my friend) returned to Belgium. Thankfully, I got a call not too long after, asking if I was still interested in the sub— he’d changed his mind!

So it ended up on my wrist. Although it was a stunning watch, there was one blemish on 11 o’clock hour marker which caught my attention more than once. Apparently, that was something Tudor could have fixed. Unfortunately, I didn’t know that at the time, and by the time I did, the Submariner had already found a new owner. Someone approached me after seeing images which I’d posted online and asked if it was for sale. Long story short, while I said no at first, some months later he bought it from me and the watch went back to Belgium again.

Speedmaster 3593.20 “Albino”

At some point, there was an opportunity to buy a Speedmaster Albino. Somehow I was intrigued by the looks of it. The creamy white dial with black hour markers matched the hands somehow. Having a completely different look and feel made me fall in love with this model. And, at some point, there was one available for a reasonable price. However, I didn’t have the money to hand. Hence I had to sell another watch to free up the funds. And although there was a buyer for it, by the time I finally sold it the Albino was long gone. As it is a rather rare model of only 500 pieces, the opportunity didn’t repeat itself for the same price.

Rolex Submariner 16610LV Anniversary

Early 2009 I came across one of the first-anniversary Submariners and bought it. It was an F-serial, flat-four in fantastic condition. The funny thing was that I bought it from someone who bought and sold the LV multiple times in years gone by. He’d been through a similar experience with LV as I had with the GMT.

Having had several Submariners in the past, something made me decide to sell the LV again at some point. Looking back, it was actually the one I liked the most due to its larger hour markers which were simply better proportioned. Needless to say that this watch, at the recent price levels we know, will not be seen on my wrist again.

In the olden days, pre-loved watch prices were a lot more attractive. When discussing watches in the office we used to say that something is “Submariner money”. That meant it was a mid-range ticket that many people could aspire to. That’s something which doesn’t work these days as the prices of these watches easily eclipse €10,000. To me, a simple Sub just isn’t worth that amount of dough.

While writing this, I am aware of the amount of Rolex watches I have owned and sold. But my journey pretty much started with that brand. Over time I have broadened my horizon a lot and sold most of the Rolex watches.  And although I might regret selling some of these watches, I definitely don’t regret moving away from the crown. You sell something for a reason and you shouldn’t look back. But sometimes it can be hard.