Five Watch Types and How to Style Them

Five Watch Types and How to Style Them

| 12.12.22

Are you new to this whole “watches” thing?

Do they all kinda look the same — vaguely round things that you wear on your wrist that tell the time? We know how you feel. We’ve been there. Thankfully, watches are classified into fairly discernible types that are reasonably easy to differentiate, once you get to know a few classic models. 

And once you can differentiate different categories and know what each watch is for, you can start thinking about what to wear with each one. Or what each one should be worn with…whatever. (You know what we mean.) Because while there are no hard and fast sartorial rules, it can be helpful to understand the context under which each type was invented, and for what activity. 

Dive Watches 

Prior to the early 1950s, SCUBA diving was a specialized pursuit largely regulated to military use, but Jacques Cousteau’s Aqualung changed that. This decade saw the debut of the Rolex Submariner, the Blancpain Fifty Fathoms, the Zodiac Sea Wolf, and several other now-iconic models that followed the trajectory of commercial SCUBA as it blazed an underwater trail around the world. Dive watches often have a highly water-resistant, often stainless steel case, a crown that screws down into said case, and a “dive” bezel — one that rotates and can be used to keep track of elapsed time. A matching steel bracelet often accompanies the watch, though rubber straps are also common.  

Wear It With: Almost nothing. (I.e. swim trunks!) However, dive watches these days are no longer just for diving — you see them worn out to dinner, you see them in offices, you see them everywhere. We tend to stop short of wearing, say, a Submariner with a tuxedo — only Sean Connery could pull this off — but you can certainly wear one with a suit these days. 

The Watch: Rolex Submariner 5513


A chronograph — from the Greek for, approximately, “time writer” — is a timepiece that includes a stopwatch feature. Using buttons on the case flank or crown, the wearer can use the stopwatch to time events, which made chronographs especially useful in motorsports, assembly lines, and even during wartime. Look for the telltale buttons (“pushers”), as well as the small sub-dials on the face that keep track of elapsed seconds, minutes, or hours. The earliest chronographs used a single button to start, stop, and reset the stopwatch feature, though most such watches employ two buttons: the first starts and stops the chronograph, while the second resets it. 

Wear It With: A racing suit and a helmet. Ok, fine — maybe not everyone is driving a souped-up 911 while wearing a chronograph — but the things really do look great while driving a fast car. Otherwise, a chronograph on a cool leather strap (preferably of the “rallye” type) looks awesome with a well worn pair of jeans, a t-shirt and a leather jacket. Keep these away from your formalwear — they’re too busy. 

The Watch: Breitling Navitimer 8 Chronograph

Price: $4,150

Pilot’s Watches

This is a tricker category to pin down. The earliest pilot’s watch — the Cartier Santos — looks much more like what we’d consider a dress watch today. From there, dedicated pilot’s watches often became oversized, for legibility’s sake. Some took on complex scales on the dial or bezel to allow for things like fuel consumption and navigational calculations. Some, such as many dedicated military pilot’s watches, are chronographs, which allow pilots to time events. Really, this is a category in which you simply have to become familiar with some key models in order to recognize the categorization. The Breitling Navitimer, the IWC “Mark” series, and the famed B-Uhren (a watch type, not a model) are all good places to start. 

Wear It With: A pair of goggles, a flight jacket, and a scarf — preferably one that’s blowing in the wind. Well, maybe you don’t actually fly stuff. But because “pilot’s watch” is such a broad category, the (proverbial) sky is sort of the limit. Any pilot’s watch is a “tool watch,” however, so it’ll probably look best in casual settings. (The only person wearing one in a suit is likely an executive from a company that sells pilot’s watches.)

The Watch: IWC Pilot's Watch Mark XVIII

Price: $3,300

Dress Watches

Again, this category is a bit harder to define than, say, that of dive watches or chronographs, but a dress watch is generally slim, simple, and often comes on a leather band that can fit under a cuff. Often a dress watch is made of precious metal, but you don’t want to attract too much attention to yourself with one — a time-only piece, probably hand-wound (for the sake of slimness) is the way to go. Some people might consider something like the Rolex Datejust (which comes on a steel bracelet) to be a dress watch, and that’s totally fine. But if you’re in formalwear, try to stick to something on a strap.

Wear It With: A suit or a tuxedo. This is the whole point of this type of watch — to accent semi- or formalwear. Of course, if you want to wear your slim gold dress watch in shorts and a t-shirt, do it! (Just be careful with it.) There are no hard and fast rules in Watches. But these sorts of pieces work best in formal settings, we’d say. Just don’t take your dress watch into the water, for God’s sake.

The Watch: Patek Philippe Calatrava

Price: $29,500

Luxury Sports Watches

This is a more modern category dating to the early 1970s, the iconic designs of which — the Audemars Piguet Royal Oak and the Patek Philippe Nautilus — sprang fully formed from the mind of one man, a watch designer named Gérald Genta. These watches often feature bracelets that are integrated to the case, shaped bezels or cases that aren’t strictly round, plus high-quality automatic movements, high water resistance, and high price tags to boot. They’re made to bridge the gap between dedicated watersports watches such as dive watches with something more refined — the type of thing that can be worn out to dinner in St. Tropez. 

Wear It With: Anything. If you’re gonna cough up the cash for one of these — which often begin at around $20,000, depending on the model — you should wear it as you damn please. Personally, we think they’re too busy for formalwear, but in a suit? Go ahead. And in a t-shirt and shorts? Absolutely. And of course, they’re sports watches, and many are made for immersion in water — just be sure to check the specs on yours, especially if it’s a vintage piece.

The Watch: Audemars Piguet Royal Oak

Price: $26,990