The Wardrobe Lessons I Wish I’d Applied To Watch Collecting

It’s a thought that sparks every watch collector’s journey: “I can have more than one watch.”

This seemingly harmless realization can begin, for many of us, a lifetime of joy, excitement and obsession (along with financial pain). Not to mention the satisfaction of a hard fought purchase or the disappointment when that purchase is less than expected. I started the journey of watch collecting about five years ago and over that time I’ve had a lot of ups and downs, made a lot of mistakes and bought and sold a lot of watches. If time travel could exist (which it can’t) I would hope this article could find its way back to me with this simple instruction: take all the lessons you’ve already learned from building a wardrobe and apply them to watches.

About a decade ago, I decided to change what I wore. I would stop doing what I had done since I was in my twenties: buying the things I liked the most out of what was on offer at the mall or a fashionable boutique. I would learn about the principles of classic menswear and try to build a wardrobe based on personal style, quality construction, excellent craftsmanship and time-tested silhouettes. However, even with those lofty goals in mind, I made a lot of mistakes. I made spur of the moment purchases. I bought items because they were popular in the online menswear world or what I thought (read: had been told) I “should” have in my closet. I went extreme with my first custom orders, for suits, shirts and shoes – picking bold colours and exaggerated features – because I was caught up in the excitement of all the options. But having come out the other end with a wardrobe that fits my life and brings me joy, I don’t regret much of this (except, maybe, the retro styled tan suit). Not only did I learn about fabric and craftsmanship, I learned about myself. What I think works best for me and my life, what brings me the most satisfaction and, importantly, what builds towards a harmonious, versatile wardrobe.

Early over-the-top experiment: tan suit and too many accessories.

Despite learning those lessons with my clothes, I made all the same mistakes when it came to watches. Buying what I read I should have in my collection. Being swayed by online hype. Going bold because bold catches your eye. I would have saved a lot of time, and money, if I had taken a slower, more deliberate route to building my collection. But it’s really not surprising, and it don’t beat myself up over it, because, like classic menswear, despite all the blogs and YouTube videos, our culture is not exactly a daily expression of horological education. In fact, when I think back to my teens and 20s, I had very similar experiences with clothes and watches.

I’ve always been interested in classic menswear, but back in the 80s I neither knew where to look for inspiration nor where to buy good clothes (if only someone had told me about G. Bruce Boyer’s book Elegance!). So I ended up with a Bogart-style trench coat and fedora hat. Yes, I was that kid in high school. It took until well into my 30s, and the emergence of the menswear internet, along with a few new shops, for me to make my wardrobe change.

My first trip to Cuba, in 2007, wearing the sunburst dial quartz on a bund strap.

Meanwhile, ever since my grandmother gave me a Timex when I was twelve, I have been in love with watches. But again, back in the 80s, 90s and even early 2000s, I didn’t know where to learn about what to buy and why. I was drawn to watches that I thought were elegant and dressy, with a strong sense of nostalgia. I remember a fashion watch with a brown starburst dial I wore on a bund strap. Or a flimsy quartz “dress” watch with a low quality stainless steel case and black dial. Both lacked good design or true beauty. They were just showy. And I stopped wearing them after just a few months because daily wear meant their cases would peel or discolour. In fact, they expressed Bruce Boyer’s much quoted saying: “good clothes look good even when they’re old; cheap clothes look cheap even when they’re new.” But my most absurd watch, the height of my nostalgic stupidity happened not that long ago, just over a decade, when I really should have known better.

I was visiting family out in BC and noticed a watch one of them was wearing. It was my kind of 1970s nostalgia incarnate. Large and rectangular, wood paneling on the dial, digital and analog read outs. And a super wide leather strap. The Vestal Monte Carlo. Essentially a station wagon on your wrist. I was immediately in love. My family member told me he’d bought it for $200. My jaw dropped. Other than Rolex, I never imagined a watch could cost that much (oh, how much I still had to learn). 

The Monte Carlo monstrousity
[courtesy Vestal Watches]

As soon as I returned home from that trip, I ordered the watch, feeling like some kind of high roller. And when it arrived, I loved it. It fulfilled all my nostalgic desires. But it didn’t take long, perhaps a few months, for the lustre to wear off. Nostalgia can only take you so far, especially this kind of tongue-in-cheek irony. It is a simulation of what you remember and love about your past. And simulations do not have the truth of experience and meaning I think we actually desire when we feel nostalgic. Plus, I was leaving the stage in my life where everything was a joke, like ironic tshirts and crazy neckties. Looking back on it now I see that the watch really is a joke. Knowing a bit about watch parts and construction, it probably cost very little to make. Most of the price I paid was for the design.

And I don’t have a problem with that, if the design is the result of hard work, research, innovation and inspiration. But the Monte Carlo is nothing more than nostalgic nonsense. Like the cheap fedora and trenchcoat I wore as a teenager. Not knowing any better, I was chasing a simulation instead of distilling what I like about classic style down to its parts, figuring out which ones work for me and my life, and then building a wardrobe slowly and with intent out of quality items.

Custom-made safari jacket, button-down shirt and linen trousers.

And that takes me to the lessons I learned from building a wardrobe, the questions I ask myself of every new garment I consider, after years of experimentation and learning:

What purpose does it serve in my life?

Does it fit into my daily activities like working from home, occasionally going out, walking the dog?

How does it harmonize with the rest of my wardrobe?

I no longer buy a garment, whether it’s a shirt or a pair of socks, without thinking about all my other clothes. Not so that things match, but so they work together. I have a lot of blues and brown and greys. When I introduce green items, for example, I make sure they’re of an earthy green, so they can be worn with most other items. The point is to have a wardrobe where each garment works with almost any other garment.

How does it express my personal style?

This is the trickiest lesson, one that requires a lot of personal work and introspection. And is always evolving. I think with my own personal journey, it was like looking for a radio station: you have to go a little past it to make sure you have the best signal. It’s also about recognizing there are things I like – bow ties, monk strap shoes, gurkha trousers – but that don’t look quite right on me.

But I didn’t apply those lessons to watches at first so I spent years experimenting and flipping. The apex came last winter when I looked at my collection – which is capped at eight because that’s how many spots there are in my display box and watch roll – and most of them were rather large sport watches. For a guy who mostly wears tailored jackets and leather shoes. Not that I don’t think those go together. But in chasing watches I thought were beautiful or interesting, I lost sight of myself. And not only did the watches feel incongruent with my life, they had little consistency within the collection. I’m not saying that every watch in someone’s collection needs to have the same colour dial or that there can’t be an outlier, but when I look at my closet, for example, my wardrobe isn’t a cacophonous explosion of different styles. Because that’s not me.

My new Seiko Bell-Matic. A bit dressy, a bit sporty. Like my denim shirt.

And so, belatedly, I did the work to refine my watch wardrobe. I shifted the balance towards dressier watches. I kept some sport watches because I do swim and fish and backwoods camp. But I didn’t need four dive watches. So with each purchase, I tried to consider those lessons I’d learned along the way.

I’ll give you an example, my most recent addition and how it connects with my life. I’ve been building scale models for about twenty years. For the first long while, it was mostly Japanese robots, but recently I’ve switched exclusively to mid-century airplanes. As a result, I’ve become more and more interested in all things aviation. Including watches. At first, I bought the watches that seemed most obvious: a Seiko Flightmaster and a Tisell type-b flieger. While I liked them a lot, and they scratched the aviation itch, they just didn’t suit me. The Flightmaster is too chunky and complicated (and I just can’t seem to enjoy chronographs). The flieger, too rugged and the design too utilitarian for me. So I sold them. But still I wanted something that evoked aviation history, while fitting into my wardrobe and collection, which is a bit dressier and refined. Then I found a much better option: the Oris Big Crown Pointer Date.

My Oris and my recently built Spitfire Mark 1.

I’ll admit that the bronze Big Crowns, which seem much more popular, don’t really do it for me. And many of the colours the dial comes in, while lovely, I find a bit too bold. But when I saw the slate blue/grey version on a bracelet, I was immediately taken. I’ll provide a full review soon, but for now this watch feels like it ticks all the boxes: heritage, elegance, versatility, beauty and a joy to wear.

The challenge I face now, having learned these lessons with clothing and watches, is to fight the urge to cast them aside and buy new things purely for the dopamine hit. Despite having all the clothes I need (more, really) I still feel tempted by a new sweater or pair of shoes. The same with watches, but much more so. There’s always a new release or a vintage discovery that gets the heart rate up. But the rule I use, with both of my obsessions, is “one in, one out.” I will not get something new without parting with something I already have. And therefore, it has be a significant upgrade. This has allowed me to weather the release of a few amazing watches the last few months and some damn fine jackets last winter. We’ll see if I can keep up my resolve.