This article is made possible by The Fifth Watches, timepieces that incorporate a timeless design with minimalist elements throughout.

Wristwatches. In today’s world of smartphones, smart watches, and clocks on every digital interface we encounter, a watch is almost pointless… at least from a utility standpoint.

“So why wear one at all,” you ask?

A man with style understands a wristwatch represents much more than what it’s designed to do.

Much like attention-getting socks or a cheeky monogram inside a suit jacket, a wristwatch showcases the wearer’s personality. It can also convey his taste, wealth, even humor (albeit, with a dose of reality).

Also, unlike women, men don’t have many jewelry options when it comes to accessorizing their base outfit.

We can get away with bracelets, necklaces, rings—not all at once, hopefully, unless you’re channeling your inner Johnny— and watches. That’s about it!

A wristwatch is the one accessory that not only serves a specific purpose, but also stands the test of time from a style standpoint, meaning, you won’t look at photos of yourself twenty years from now and say, “Oh man, how embarrassing, I can’t believe I’m wearing a watch in this photo! That’s so 2015!!!”

Since we’re striving for classic and timeless when possible, here are five watch styles to add to your growing collection. When you find yourself in the market for a new watch, keep these characteristics in mind.

Before we get started: Keep in mind that even though I’m presenting you five different styles of wristwatches, you may find you only need one.

Maybe, after assessing your lifestyle and daily activity, you realize you need three different types, or that one style can serve two purposes, and so on.

This is simply a guide to help you understand what to look for. Tailor this list to your specific situation, and decide what makes the most sense for you.

What we’ll cover:

  1. basic characteristics of each watch style
  2. appropriate situations to wear the watch (formal, everyday, casual, active)
  3. an affordable option, and a splurge option

Style 1 & 2: The Dress Watch with Leather Strap

Five Types Of Watches To Have In Your Collection

Characteristics: Slim, understated profile; metal case; simple watch face; leather strap.

Price points: $100-$1000 (affordable); $5000+ (splurge)

Also useful for: Everyday

Affordable: The Fifth Tribeca

Splurge: Patek Philippe Calatrava

When you’re attending a formal event—anything from a traditional wedding to a black tie event—classic and understated is best.

Your accessories should match the formality of the event itself, and when it comes to your watch, a simple style with a light-colored face and black leather strap is perfect. (It goes without saying that your leather shoes and belt should also be black.)

For “dressy casual” or business casual situations when you’re still in a suit and / or tie, a similar watch with brown leather band would fit the bill.

Style 3: Metal Sport Watch, Tool Watch, or Activity-Specific Watch

Five Types Of Watches To Have In Your Collection

Characteristics: Larger case; metal or leather bracelet; activity-specific features such as chronographs, altimeter, depth gauge

Price points: $150-$500 (affordable); $2500+ (splurge)

Also useful for: Everyday, Formal (sometimes)

Affordable: Seiko 5 Automatic

Splurge: Rolex Submariner, Tag Heuer Monaco

I’d classify a fashion watch as something that can be used in a variety of casual situations, and combines form and function in a way that speaks to your personal style. This may or may not have a fashion brand name attached to it (i.e. a watch made by Burberry).

Sometimes, a fashion watch can be worn in dressier situations. For example, I have a Gucci Pantheon steel watch I wear most days. I put on shorts and a T-shirt, I wear this watch. I put on a suit, and if I want to, I can wear this watch.

It’s flexible because its design is understated and its face unadorned (well, other than the black mother of pearl).

“Activity-specific” refers to the features that are built-in to a watch for a specific purpose. Diving watches are built to withstand underwater pressure, pilot watches typically have bigger numerals and dials so they’re easily read and adjusted at a glance.

All this to say, you don’t necessarily have to be a pilot, a diver, or a race-car driver to enjoy watches that are specifically built and designed for these activities.

A lot of it comes down to preference, so if you like something and can afford it, buy it. Just make sure you’re wearing it in the right situations–in this case, not to a formal event.

Style 4: Sport Watch with Rubber Strap

Five Types Of Watches To Have In Your Collection

Characteristics: Substantial in size, yet often lighter-weight case; rubber or nylon strap; sport-related features (lap timer, countdown timer, compass, chronograph); can be digital or analog

Price points: $50+ (affordable); $1000+ (splurge)

Also useful for: Active only

Affordable: Luminox Sentry 0200

Splurge: Brera Orologi Supersportivo

Sport watches are fun to have when you’re working out, playing sports, or just being active in general. They’re usually more lightweight and able to take a beating.

My favorites always have a rubber strap, easily cleaned after the game or a strenuous workout. Depending on your sport of choice, these watches usually have built-in features like timers (or chronographs if analog), water resistance (for diving and swimming), backlit screens or dials (for nighttime use), even compasses and altimeters.

Style 5: Everyday Casual Watch

Five Types Of Watches To Have In Your Collection

Characteristics: smaller face; metal casing; nylon, leather, or metal strap; affordable

Price points: $20 (affordable); $500+ (splurge)

Also useful for: Casual, Everyday only

Affordable: The Fifth Black and Tan, Timex Easy Reader

Splurge: Uniform Wares C35

This the kind of watch you wear on weekends, running errands, seeing a movie, things like that. You’re not going anywhere in particular and you don’t need a special watch for the occasion.

My go-to has always been the Timex Easy Reader on a NATO strap, although lately I’ve been drawn to The Fifth’s Black and Tan model.

Since these watches are daily wearers, I wouldn’t hesitate going the more affordable route. There are plenty of options that come in leather (like the Black and Tan) or metal, and some whose bands you can swap out for nylon (like the Easy Reader).

In Conclusion

If you’re in the beginning stages of building your watch collection, find one type that you need most, and purchase that first.

If you don’t suit up very often, and instead, are a scuba instructor, then invest in a diving watch.

If you’re climbing your way up the corporate ladder, a black leather dress watch would serve you well five days a week.

As your budget allows, tackle the other categories in order of necessity.

Extra Credit: While this isn’t an all-inclusive guide that covers wristwatch anatomy and terminology, here are a few great guides you can read for extra credit (1, 2, 3).

Learn a few shortcuts to dressing well

Enter your first name and email, and I'll send you a free eGuide with quick and easy tips you can use today.

16 Responses

  1. crockeronline on

    Good article…? All these are good tips, I think style-conscious gents can get a lot of classy mileage out of these five watches (maybe a couple extra NATO straps). But I have to say, that first link to The Fifth is a bummer- those watches look great, but the egregious email harvesting and gatekeeping is really annoying. I noticed below this is a sponsored post, so I suppose that’s the explanation.

    • Barron on

      The Fifth only releases their collections for five days out of the month, and they notify peeps on their VIP list first (to get early previews, early opportunities to buy, etc.) Thus, the email collection. I personally don’t find a problem with it, if I like the watches and I want to be notified ahead of time. I sign up for lists all the time to get the “inside scoop” or whatever.

      And while the post has been made possible by The Fifth, hopefully you find it is honest and unbiased, with many different options, depending on what a guy is looking for in a watch 🙂

  2. Andy Budnik on

    Technically, EG got me started with my watch obsession. I felt I needed a watch to make an outfit go. Then I needed one for each occasion. Now I have 8 with the intention for more. I’ve found a great interest in them and love wearing the different styles I have to complete the look.

    I’d say that the first watch anyone needs is that simple grab and go for any occasion. Metal with a black face that can be dressed up or down. Divers work great, but most watches with a black face and stick indices and rather sterile dial work. If you have one watch only, an automatic would be a good choice. If multiple, you definitely need a solar in there.

    Most people will only need one dress watch. Can always get a second strap for it, but I do prefer brown and gold to brown and silver, so I see where you’re coming from. A better #2 might be a chronograph – slightly less dressy, but acceptable in many different situations.

    #3 is better described as “tool” watch. In my definition, “fashion” watches are designed by companies that do things other than strictly make watch, ie Guess.

    #4 – there’s no substitute for a G Shock. They aren’t the most popular watch in the world for nothing.

    I know this post is sponsored, but I will only buy from watch companies after having some bad experience in the inexpensive fashion watch world. When in doubt – go with Seiko. They make beautiful watches with tons of value at every price range.

    • Barron on

      Great comment! Love the way you laid it out, and I would pretty much recommend that order as well. I think for me, divers are a bit too “sporty” for suits, and I’d prefer something like the Seiko Cocktail Time (www.amazon.com/Seiko-MECHANICAL-Shinobu-Ishigaki-SARB065/dp/B0038OLUMM) which has a simpler dial and indices, like you mentioned.

      • Andy Budnik on

        I love the Cocktail Time…there’s no better dress watch under $500. It looks amazing on a cognac crock leather.

      • Andy Budnik on

        I don’t really have any duplicates, but I really like Steinhart, Citizen and Bulova. Orient is a great watch for the money in terms of affordable automatics as well. I just saw a Sinn I really wanted, but I’m not sure I’ll ever justify spending more than $600 on a watch…

  3. TMann on

    I think that the vast majority of men could get by with one or maybe two watches. Your “main” watch should be a nice, but sporty watch: a diver, chrono or “pilot” watch with a metal or nice leather band. This type of watch is appropriate for 99% (or 100%) of ones needs, especially if one doesn’t wear a suit to work. If a man does a suit or formal wear with any frequency, a nice dress watch would be a good second option. And if you wear a watch in bad conditions, perhaps an inexpensive “beater” watch would be useful and would minimize wear on the “nice” watches. So one, two or at most three watches should be sufficient for almost everyone.

  4. kmoney on

    If you can buy only one watch , I would throw a vote in for the Omega Speedmaster Professional — even an older one from Ebay. Can easily be dressed up or down and is understated, timeless, and iconic enough to be respected by watch enthusiasts and non-enthusiasts alike. It will also make a good investment piece.

  5. qin on

    I will buy one dress watch and even wear it with sportswear or formal wear.

    Dressing up the accessories won’t a problem.

  6. Mark on

    Perhaps I don’t socialize enough with captains of industry and the social elite.

    I must say, these days I’m one of the few guests at formal weddings who is even taking the trouble of wearing a suit, tie and Oxford shoes. Not to mention a suit that is less than 10 years old.

    I’m sorry to say that these formalities of gentlemen dress codes barely exist anymore in the middle class.

    I have a leather banded dress watch but I prefer wearing my stainless steel diver watch albeit it’s a Breitling and my choices are a couple of cuts above the boorish guys wearing a polo shirt, khakis and answering their phones during the wedding! And they probably make more than my salary man dollars!