Sartorial pursuits aren’t the most immediately accessible for the layperson; how are you meant to know what goes with what, and how are you meant to try new things without risking judgement from the Fashion Police? Luckily, the Fashion Police is nothing like – and a new wave of menswear influencers like X (formerly Twitter) mainstay Derek Guy, aka DieWorkWear, are encouraging a curious approach to taste and fashion.
If you’re reading this, you want to start wearing watches – good ones – and you’d not quite sure where to start. It’s easy to wear the wrong watch, and easier still to wear the right watch in the wrong way. Here, we’ll move forward with curiosity and positive intention, to find out just how to wear a watch.
Find Your Taste
The first step into any niche is a fretful one, because there’s so much to learn. The world of watches is a subset of a wider world of fashion, and they are inextricably linked; in order to find the right watches for your wrist, you need to have a handle on which clothes are right for your style. This means building your taste, while building an idea of what forms different styles. I’ll give you a hint: it’s culture.
Treat your wardrobe a little like a logic puzzle, and you’ll start to get a handle on your taste. If there’s a specific style of hunting jacket you like to wear, for instance, what clothes might fit it? Maybe clothes that mid-century hunters would have worn? Extend this to your watches; what would have been practical? Can you now see how fashion is built on practice? Let this guide your thinking, and you’ll start to see connections everywhere.
Building a Collection
One watch is never enough. This is something you’ll already have surmised by our acknowledgement of outfits and taste above; just as there’s a fit for every occasion, there’s a watch for (nearly) every fit. Don’t be afraid to accumulate some options! This needn’t be an expensive hobby either, as it’s possible to get verified prestige-brand watches on the second-hand market. Rolex watches are popular to buy pre-owned, and very easy to trade with if you want to rotate your collection accordingly.
If The Watch Fits…
Of course, there are logistical considerations to wearing a watch, too. They need to be sized right for your wrist, both in terms of the size of the strap and the size of the face itself; you don’t want to dwarf your wrist with something tastelessly attention-seeking.
In terms of the strap, you can always find a strap that fits your wrist – but you want the strap and the face to be proportional, so these should go hand in hand. Use a piece of string to get your wrist circumference, then measure it; this will tell you where to start.





