A watch is the most important and wearable fashion accessory a gentleman can own. Although useful for telling the time, your choice of timepiece also tells the outside world a great deal about you.

I am especially drawn to watches as an accessory — mostly because their fit is unaffected by a fluctuating waistline. And yes, I know you could put shoes into this category. One can drop thousands on multiple pairs of footwear. But there’s one major problem: they soon wear out. A decent watch should last a lifetime, be a good investment and a subtle indicator of both class and wealth.

Yet there’s a very fine line between being classy and vulgar — and a distinct danger that one can fall into a fashion trap. Personal taste in timepieces has been further complicated by the wearable tech dilemma. I’m calling time on this trend — wearable tech is the new naff. No one likes a Fitbit bore.

I’ll admit it took me a while to recognise that I, too, had entered the tech fashion bubble. When Apple first launched the Apple Watch, I resisted and didn’t buy the first edition, mostly because I thought they looked horrible, but they weren’t water resistant and didn’t do much. By the third iteration, I was sucked in as they had become a “must have”.

As well as the daily challenge of closing one’s activity rings, the Apple Watch has interchangeable digital faces, including a talking and moving Mickey Mouse, a huge range of attractive straps and genuine usefulness — such as the ability to swipe your wrist to make contactless payments if you “go royal” and forget to carry cash.

I can use my watch to pay on the bus. And in Waitrose. Plus it’s possible to scan a digital boarding pass on my wrist and sashay through the airport barriers. However, the novelty of doing all of this has long since passed. No one cares. Rather than appearing noble, there’s a distinct possibility one will simply look like a nob.

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The democratisation of tech has also ruined the investment case. The Apple Watch is not a glistening prize, it’s a wasting asset. Even the £1,399 Hermès edition. That’s just techspensive.

There’s another reason I’m turning away from tech. I am convinced that my smartwatch is spying on me. It has been cruelly suggested that it’s just the fatness of my wrists that makes my watch listen to me, activating Siri without me realising.

James Max’s Apple Watch turns sarcastic © James Max

Last week, I was on the phone organising some fancy cars to come down to the lawn tennis club of which I am chairman. “Do you want to bring a new Ferrari to the club tomorrow?” I asked. The next thing I know, my watch sarcastically answered: “I have very few wants.”

As a result, I too have one fewer want. I no longer wish to wear this meddlesome watch.

My grandfather once told me: “You can never have too many watches.” You may have guessed that he was a man who had too many watches and, as a result, I now own three expensive classics — a Rolex Datejust (old school, quality), a Patek Philippe Calatrava (wonderful as a dress watch), and the pièce de résistance, a Patek Philippe Nautilus from the 1970s. In gold.

Since I am splitting up with Siri (Apple’s digital assistant), I will have to return to wearing a formal watch every day. The issue is — which one can I wear? Or should I cash in my collection and start again?

My banking and private equity days provided the best guide to this. For example, diamonds may be a girl’s best friend, for blokes there is never an excuse for any watch that has a diamond anywhere near it.

Before it became an essential part of everyday financial services practice, if a client turned up with too flash a watch, you’d always have them checked out for money laundering. Too much bling and ice creates the wrong impression. And it’s the same with gold.

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Is the Apple Watch featuring Disney characters really the height of sophistication? © Apple

Over-engineered watches are also out. There are many watch brands that have rapidly passed in and out favour; IWC was one, Hublot another. Oversized faces and too many dials and you’re straight back to spiv territory.

In a financial work environment, you know someone is doing well when they arrive at a meeting with their Hermès tie loosened, top button undone, double cuffed shirt with cufflinks out (probably left on their desk near the ‘phone) and two casual folds of the shirt sleeves. Just to the forearm. The only reason for this kind of dress is to display a brand new watch.

There’s something rather splendid about the glint of polished brushed steel. Not too shiny, nor overcomplicated. Yet my Rolex Datejust is a bit too common. If there’s a leather strap, you’re confusing night wear with daytime, so that’s the Patek Calatrava relegated to the dressing table. Too much gold and you lack taste. So that means the Nautilus won’t ever be aired. Simplicity, exclusivity and an established brand is what you want. And your timepiece needs to be the right size — chunky without being overbearing.

While I have plenty of watches, plus my own relics from the 1990s “let’s have a sports watch” trend, none is suitable for everyday wear. Even my Cartier Santos in yellow gold and steel, bought during a distant bonus bonanza. It works with a pullover and the convertible. But not for everyday.

It’s time to consult my millennial friends. True, many of them eschew the watch altogether, and just use their phones to tell the time. Savages. But the more enlightened are leading the resurgence in turning away from tech and towards the classic brands.

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Ironically, using tech to boast about their timepieces is powering this market. Second-hand watches have never been more “in”. Buyers look for an enduring brand with Instagram-ability, credibility and rarity. One enduring brand that’s having a real renaissance is Rolex.

It’s not just the classic charm and timeless design of older watches that appeals, it’s the inability to just buy one off the shelf. Online platforms, such as the trading site chrono24, mean there is total visibility on pricing. Buying boxed and with original papers is best, but not essential. Buyers will pay a premium for exclusivity and limited editions — something that might make you see your own watch drawer in an entirely new light.

In my search for a well-made, truly limited edition timeless classic I had a stroll around Bond Street. Some watches that fitted the bill — and my wrist — commanded tens, if not hundreds of thousands of pounds. Probably a step too far.

One friend, who happens to be a millennial, spent a lot of time looking for the right watch and ended up with a Rolex Submariner. It’s a smart choice; a classy everyday watch, not overly expensive at eight grand, and I reckon its value will hold.

Time to see if I can trade in my gold Nautilus, drop a proper Rolex into the collection for everyday use and pile the leftover cash into my bank account. After all, it’s been a while since I last bought a classic car.

James Max is a property expert and radio presenter. The views expressed are personal. Twitter: @thejamesmax. If you have a problem for James, contact him at richpeoplesproblems@ft.com

This article has been amended since original publication to correct the name of the Apple Watch





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