Understanding The Principles of Classic Menswear Through Watches

When I went to my first Red Bar meet up—that somewhat exclusive global network of watch enthusiasts—I knew I was going to see some amazing watches. Rare Pateks. Vintage Omegas. Ultra expensive Rolex. And I wasn’t disappointed. But what I didn’t expect was how most of the other guys would dress: like they’d come to mow the lawn.

I know that shouldn’t surprise me. Our culture today, especially in American and Canadian cities, is extremely casual. But in my mind there was a disconnect between the elegance and style of some of those watches and how their owners were dressed. When I asked a few guys about it, they told me they didn’t think of their watches as a part of their wardrobes. Even though they wore them. And, like many guys today, they didn’t really know or want to know how to dress “up.”

But even though most would claim ignorance when it comes to dressing—or wouldn’t know where to shop for a jacket and trousers if they wanted to—I would argue that most of us do know the principles of classic menswear. My proof is that that information, that knowledge, is embedded in our understanding of watches.

Before I dive in, I want to make it clear that I don’t consider any of these principles to be rules. They are simply guidelines, tried and tested strategies for achieving a certain style and balance in your wardrobe. People can and do, of course, ignore or try to reinterpret these principles but regardless, they are present in our subconscious and they serve a purpose in our society.

A pair of patent leather oxfords with ribbon laces, for black tie. The toe cap is traditionally not favoured because of the extra decoration.

The Principles

I’ll begin with decoration. The simpler an item, the more formal. Conversely, the more decorated, the more casual. In leather footwear, for example, a shoe where the upper (the top of the shoe) has no pattern, no broguing, no layers or sections is more formal. An oxford, for example, is more formal than a derby because the bit of leather the laces go through is part of the upper, not attached on top of the upper. A figurative step further, replacing the laces with a bow or nothing at all, and you have the most formal of all shoes: the opera slipper. Go in the other direction, and things become more casual. Start adding broguing, wingtips and so on, and the shoe becomes less formal. 

Brogued wing-tip derbies, which may look dressy, but are on the casual end of leather shoes.
[Courtesy of MAROL]

And then there is colour. The most formal tones are black and white, an actual lack of colour. In many cultures, black and white are associated with birth, marriage and death. Big, important, momentous stuff. Stuff that demands seriousness. Not to mention specialness. White clothing, for example, is difficult to keep clean in most places throughout most of human history, so it was and is saved for rare occasions (or the very rich). The tuxedo, which evolved out of white tie, is Europe’s cultural epitome of that specialness. 

Start to add colour to clothing, and things lose that sense of formality the further along the colour spectrum you go. A dark blue suit and white shirt is still pretty formal, but change that suit colour to brown, the shirt to blue or patterned, and it’s no longer a combination you’d wear to a funeral (I hope). 

The clean, sharp lines of the blue suit give it formality, while the soft construction and finish of corduroy is more casual.

Something that is more subtle but equally as impactful is silhouette. Unexagerated and based closely on the natural curves of the body is classically formal. Along these lines, a certain stiffness, in shape if not appearance, is typically considered more formal. As you introduce softness or exaggerated shapes, the garment becomes more casual. On one end of the scale, I’ll return to the classically tailored tuxedo. The jacket and trousers are neither boxy nor tight. The shoulders have definition but are neither extended nor soft. The lapels are neither too wide nor too slim. On the other end of the scale, a southern Italian summer linen suit. A bit spacious, to allow cool air to flow. Very little structure, so that the jacket looks soft and easy going. Silhouette, however, is not a hard and fast rule. There are plenty of softly tailored silhouettes that while more relaxed, are still quite formal. But the overall impression is still there: streamlined means elegant, chunky means casual.

How This Plays Out In Real Life

I’m going to illustrate these principles with a couple of examples, first in clothes and then in watches.

Imagine you’re building an outfit around one item, a blue sport jacket. (If it has metallic buttons or broad stripes, you can call it a “blazer,” but otherwise, keep it simple and just say “sport jacket.”) If you are to pair the jacket with grey worsted wool trousers (finely woven fabric that can have a bit of a sheen, like in a typical business suit), a white shirt, mini-patterned tie and dark brown oxfords, most people would say that’s quite dressy, even formal. The colours are muted, the patterns limited. But lose the tie, replace the shirt with a button-down, khakis for trousers and mid-brown derbies, and it’s more casual, although what a lot of people would still consider dressy, mostly because of the jacket. Finally, wear the jacket with an open collar dark popover shirt and jeans, boat shoes on your feet, and you’re ready for a sharp, but casual outdoor event.

I think most people, without knowing exactly why, would feel the same way about these different outfits. The jacket, long associated with formality and business, would keep them “dressy” but the variations of what is worn with it, playing by the principles described above, would take it down the ladder of formality.

I would argue that the equivalent of a blue sport jacket in the watch world is a Rolex Datejust. Classic, sober, dressy and established.

I would argue that the equivalent of a blue sport jacket in the watch world is a Rolex Datejust. Classic, sober, dressy and established. On a black alligator strap it can be worn with Black Tie. Add contrast white stitching and the watch would look quite a bit less dressy. As would a brown strap, suede even more so. Worn with the original bracelet, which has a sporty legacy, and the watch is still dressy enough to wear with a suit, but can work with smart casual outfits. Finally, put the Datejust on a nato, and while still retaining its classic dressy nature, it can be worn harmoniously with casual summer clothes like shorts and a tshirt.

These principles are obviously routed in certain cultures, in certain times. I know that in Korea, for instance, a formal hanbok will include almost every colour of the rainbow and be as spacious as a tent. But the dominant world culture is still based on principles established from Northern Europe and they are so ingrained in many of us, we don’t even know it.

Why This Matters

Why do we call a simple, three-handed watch with a thin case a “dress” watch? Why would most people say a Seiko orange monster looks out of place with a sharp business suit? And as much as people bend the associations—after all, guys have been wearing sports watches with suits since Mr. Connery’s days—we are still aware that it is a mismatch. We know that because, deep down, we understand the basic principles of classic menswear.

I point all this out because if you have a gut feeling about the formality or casualness of certain watches, then chances are, you already know what you need to know about building a wardrobe, or adding a few items to your current closet. If you want to get a new button-up shirt for the office that’s a bit dressier, stick with solid colours. But if you want to look a bit more casual, get stripes. More pattern than that, like plaid, is probably too casual for a sport jacket and would look best on its own, if that’s how you’d prefer to wear it.

But I’d like to finish by setting aside all this stuff about principles and focus on what really matters. Like swapping straps and bracelets on your watches, dressing should be about enjoying yourself. Once you feel comfortable with these principles, then the goal is to stop thinking about them. Wear what you like, that’s well made and fits you well, and that harmonizes with what you are doing, and enjoy it for that reason. And, like a great watch, because it just looks so good.