You’re an astute style student and long-time reader of Effortless Gent. So let me ask you:

  • Would you wear your everyday gym sneakers with your nicely pressed trousers?
  • How about a tuxedo jacket with sweatpants?
  • Would you wear a hooded sweatshirt as a mid layer under your suit?

I have a feeling that when you visualize these combinations, something seems a little… off.

For each one, there’s a lack of congruency between the individual pieces that make up the outfit.

And as you know, putting together a solid outfit doesn’t end with your clothing. You want your shoes and accessories to also make sense with the outfit you’ve put together.

It’s not always easy to choose the best watch, because like shoes, they come in different shapes and sizes, are made from a wide variety of materials, and serve a myriad of purposes (yes, other than telling time).

In this article, I’ll equip you with the knowledge you need to pick the right watch for every outfit you ever wear.

Why the focus on wristwatches?

Watches are purpose-built pieces of machinery. Most of them are designed for very specific situations and functions.

You have your basic, no-frills watch on one end of the spectrum (i.e. the Timex Easy Reader), and on the other, mechanical watches with multiple complications… and everything in between.

Since we’re a style site, we’re going to consider a wristwatch’s design, purpose, and style when showing you how to pair it with your outfits.

Sure, you could wear a digital Casio with your suit. But that’s just like wearing your gym sneakers with your dress trousers… odd and mismatched in the most awful way.

Matching your watch to your outfit is not as difficult as it seems, once you know what to look out for.

Picking the right watch: A straight-forward approach

how to match your watch with your outfit

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First, take a look at your outfit. How would you categorize it: sporty, casual, dressy casual, formal?

  • Working out, doing everyday errands? sport or casual
  • Having dinner with friends, going to the movies, visiting the in-laws? casual
  • Attending a wedding or similar formal event? Anniversary date at a fancy restaurant? formal

Next, check out your watch selection. Evaluate the following elements when trying to decide if a particular watch leans more toward the casual or formal end of the spectrum.

Watch case material and size

This is probably obvious: if the case—the main “body” that houses the movement—is a precious metal (yellow or white gold, platinum) or mimics a precious metal, there’s a good chance your watch is more on the formal side.

If it’s made from steel, plastic, or other materials (ceramic, titanium, carbon fiber, etc.), it’s most likely not a formal watch.

As far as size, most men’s watches are between 36mm – 50mm in diameter. Formal watches are typically on the smaller side (36-40mm), while sport-specific and fashion watches can be seen across the whole spectrum.

In general, casual and sport-specific watches are larger than more formal watches. Some fashion brands take it a bit too far, and, while novel, can look like you’re wearing a wall clock on your wrist. Avoid these.

Watch Dial

On Time: Choosing The Right Watch For Your Outfit

Does it have stick or Roman numeral indices? Stick or Roman numerals tend to be found in more formal watches, while Arabic numbers are commonly found in more casual watches. Of course, there are exceptions to both.

Is the dial elegant and simple, or does it have multiple functions and complications?

The simpler and more elegant, the more formal the watch. When a watch is built for a specific task and has more complications (stopwatch capabilities, time zone distinctions, depth measuring), the more casual it is.

Watch strap

Worn-in leather looks better with jeans than it does with a suit. Thicker, bulkier straps are better with casual outfits as well.

Glossy, slim, and thin leather bands are better with formal attire, and don’t pair as easily with denim and other casual clothes.

Classic metal bands can go either way, but if your watch is sport-specific (chronographs, divers, etc.) it’s meant for more casual wear, or that particular sport.

how to match your watch with your outfit

If you want versatility…

If you’re looking for a versatile alternative that can work well with a number of outfits, consider buying a simple watch with a leather or metal band and uncomplicated dial.

Then, invest in a few inexpensive watch straps. Most watches allow you to easily swap out bands with a spring bar tool.

If you look online, there are countless photos of higher-end watches on nylon NATO straps, a perfect example of versatility and a high-low mix.

Some brands (like The Fifth) include an extra leather strap with each watch. Pretty great deal, if you ask me.

This band strategy will allow you to use your one watch in a variety of situations, from casual to formal, and anything in between.

Shortcut: A few clear-cut combos

If you can identify your wristwatch as any one of these combinations, then it should be easy to determine whether or not it’s appropriate to wear with the outfit you’ve chosen.

  1. Simple dial, roman or stick indices, glossy leather or exotic hide strap? Dressy.
  2. Digital interface, rubber strap? Sport.
  3. Complicated dial, casual band (e.g. rubber, NATO, metal, worn-in leather)? Sport or casual.
  4. Specific purpose (e.g. diver, chronograph)? Sport or casual.

Not as clear-cut a decision? Look down.

Dressy casual? “Creative” Black Tie? Which wristwatch do I wear?

If you’re all dressed, there’s a good chance you already have your shoes on, or at the very least, know which pair you’ll be wearing.

Where do your shoes fall on the formality scale?

If your shoes are formal (i.e. black oxford cap toes), go with a formal-looking watch.

If your shoes are casual (sneakers, boots, boat shoes) then your watch should also be casual, or all-purpose.

What if you’re wearing cognac-colored loafers? There’s a good chance your outfit is dressy casual, so avoid your digital Casio. Stick with something that has the same level of formality.

On Time: Choosing The Right Watch For Your Outfit

Want to make it even easier? Simply match the leather.

Black leather shoes? Choose your watch with the black leather strap.

Brown chelsea boots? Choose the watch with a brown leather strap, or one with the same level of formality, like a metal band fashion watch.

Luckily, it’s tough to mess up

For the most part, you can’t go wrong, as long as you don’t mix up two pieces from opposite ends of the formality spectrum.

In the end, you don’t want to think about it too much. Remember, dressing well should be enjoyable and, for the most part, effortless. No one’s gonna notice if your watch is slightly more elevated than the rest of your outfit, or vice versa.

Pay attention to key details in your watches, and you’ll have an easy time picking out the right one so your whole look is cohesive and well-put-together.

The Fifth has a great collection of minimal, classically-designed wristwatches—and like I mentioned earlier, their newest New York collection comes with interchangeable straps. Their styles range from casual to formal, so make sure to check them out.

The watches are only available from the fifth to the tenth of each month. Last month, a few of their styles sold out completely. Your best bet would be to get on their VIP list to snag early access and guaranteed availability.


What other hangups do you have with choosing the right watch for your wardrobe? How about your other accessories? Any trouble there?

Let me know in the comments below!

This article is made possible by The Fifth Watches, timepieces that incorporate a timeless design with minimalist elements throughout. Gain exclusive access to their October 5th release.


All photos via their respective owners.

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