Classic Watches, Timeless Design

What is a classic watch? It’s a big question. A classic watch looked good yesterday, looks good today and will look good tomorrow. A classic watch illustrates the “best practices” of watchmaking, from design to mechanics. A classic watch is equally stylish on the wrist of almost any man, and in almost any situation, formal, professional or, heck, even casual. A classic watch isn’t conservative — it’s the most forward-thinking investment you can make in a timepiece. It should be your first major purchase, your longest-lasting standby, your go-to. It should be dependable, and in putting it on, should evoke that manliest of feelings: a sense of responsibility, commitment, patience. It should, in short, be one of these.

1. Raymond Weil

Two-tone watches in steel and gold present a unique blend of both class and humility — the gold is luxurious, the steel implies that you have a strong sense of self-worth. Raymond Weil offers gold-plated elements on this Freelancer model, which makes for a handsome, yet slightly less conservative, statement. $2,150

2. Tudor

Sometimes a classic watch isn’t for everyday wear. The Tudor Glamour is a black tie watch. Curved lunes add a decorative flair to what can sometimes be overly minimalistic designs, at least for some people’s tastes. $3,350

3. Chopard

In the heart of Swiss watchmaking country, Chopard operates their venerable L.U.C production facility where the brand’s most elite timepieces are produced and hand-finished. Broadly sized, this model in gold expresses classic style with the addition of some complications for those who love mechanics as much as looking good. $29,220

4. Cartier

The famed Cartier Tortue collection is quite literally named after its tortoise-style case, which combines a tonneau shape with distinct lugs. There’s a French old-world, pre-war charm to the Tortue, which allows even new models to feel like a reminder of another age. $23,220

5. Tissot

Because of their often-uncomplicated design, high quality watches in this genre can be more accessible. Tissot adds a masculine sense of purpose to an extremely versatile classic dress watch in black and steel with a Swiss quartz movement. $375

6. Guess

This watch goes back to basics: a mostly minimalized dress watch with a classic silver dial, matched to a thin steel case and high-gloss brown leather strap. This is how a simple watch can become an indispensable fashion accessory. $115

7. Montblanc

This is a modern approach to classic design. The steel band suggests a bit more style and edginess than such a design would otherwise evoke on a leather strap. The strong hands suggest purpose and importance. $3,210

Wool coat ($1,295), cotton suit ($1,050), cotton shirt ($205), silk tie ($185), silk pocket square ($55), leather belt ($165), leather shoes ($675) and leather bag ($2,195) by BOSS. Styling by Joanne Jin.