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

click to enlarge

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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15 Responses

  1. ryan06 on

    This is a great topic and one that I have always wondered about as I start spending more on watches.

    My goal is to spend more than I ever have on a diver watch. I have been convinced that it is the most versatile piece you can own – wear with a t-shirt or rock it with a suit a la James Bond. What are your feelings on this?

    Additionally, I am a bit OCD about color coordination. I wear a lot of navy but not a lot of black. Can you wear a black face/bezel watch with a navy suit when you match it with tan shoes and belt? If not, are there other ways to do it to show off that most important piece on your wrist without ruining your outfit? What I do now is match shoes, belt, and leather watch strap but I would like to know that, once I get that diver, I can get away with a metal strap, black face watch while wearing that navy suit.

    • Andy Budnik on

      This is a big topic on watch forums. Most people say just match the leather to the shoes and accessories and a bracelet goes with anything, but is less formal. I am with you on the divers, love them and wear them with anything. I have found I love white dials and there are divers with them. Check out Christopher Ward C60 Trident – I want the white dial and black bezel and would wear it with anything. I have a tough time with black as well wearing it with blue, but have seen plenty of black dials and brown straps go w/ blue. If the dial is plain enough, it works. Divers, though, aren’t really built for leather. I have a Steinhart Ocean Vintage Military. They’re a micro Swiss company that makes some awesome watches. This one is a black bezel with grey dial and yellowed indices as an homage to the Rolex Submariner made for the British military. As the real piece is extremely rare, almost no one has it, so it’s less of what some may consider a “copy” than other Ocean models. Mine goes with anything. Took me a while and lots of pics to be sold on the look, but extremely happy I did.

      • ryan06 on

        Glad you mentioned the CW. I have the new SH21 movement in my sites and will be my wive’s Christmas gift to me! Looking at black face/black bezel and the metal strap. They just came out with their own Black Friday deal – 15% off everything from now until Christmas Eve.

        On a whim, I bought the Orient Mako this summer (blue bezel/face). It has been really versatile as I throw it on any NATO or a tan alligator strap that I just bought (still trying it out, not sure of my thoughts on it yet).

        Another piece I have my eyes on is the TAG Carrera twin time with the white face. Kind of a nice, elegant change up to a diver.

        Thanks for your advice as I have a lot of ground to cover in my arsenal but I do appreciate watch ‘nerds’ such as yourself. After all, it’s those nerdy characteristics that make some watches stand out over others!

        • Andy Budnik on

          Glad I could help. The C60 is a beauty. I have the blue Mako as well, wear it with a lot of stuff. That Tag is great too. I’d just choose one though – I sold a bunch to get it down to ten, eight that I really wear. I really want just like 5, but I’d find it hard to let any of them go at this point.

    • Barron on

      I agree w/ Andy above that you can totally wear a diver w/ a suit, and that for the sake of “drawing the line” for this article, I suggested to avoid it… but it’s not totally necessary. As with all matters of style, practically anything can be pulled off if done well.

      I recently bought a steel watch with black dial. My intention was to be able to wear it in any situation, independent of the outfit. I’m like you, in that I wear navy much more than black. I don’t see a problem with it. I feel that the steel / black can stand on its own.

      • ryan06 on

        If James Bond can do it, why can’t I, right? All I need is the cash to pay for that Seamaster… and the car, gadgets, and women. But besides all that, why can’t I do it?!

  2. Andy Budnik on

    Actually some good tips for choosing a watch. As someone who owns ten watches and reads and participates in watch threads (nerd alert), I tend to be pretty picky, (not snobbish) about the watches I have. If you’re going to have two watches, get a dress watch and a dive watch – if you like that style.

    For a dress watch, I think a white dial with Roman or stick indices is the best. Always buy the watch on the bracelet if it has one. It’s nice to have the option and finding aftermarket bracelets is much more difficult than finding leather and nato. I have a Seiko Kinetic that fills this void (SRN055), as well as my most favorite, do it all and wear in every situation watch – Rado Diastar classic original with white face. Dressy enough to wear with a suit, but looks great casually. 100M WR (water resistance, I won’t buy a watch with less than 100M), scratchproof hardmetal tungsten carbide, sapphire crystal, and a common, but eleabore grade ETA movement.

    The others run the gamut of dressy/casual. Three divers, with my favorite being a Steinhart Ocean Vintage Military. If you’re on a budget, the Seiko SKX007 and Orient Mako are great choice. I also have a Citizen Eco Drive and two Bulova quartz’s.

    Other stuff to be aware of is the materials. Sapphire glass is huge for me since it’s basically scratchproof. Water resistance means a lot to me as well, since I tend to always be wearing a watch. It’s nice to be able to take it in the water as well.

    Lastly, for the most part, no one notices what’s on your wrist. I’ve seen more people ooh and ahh over the crap fashion watches like Guess and AX, than real watches that will last 10 years or more from Seiko, Longines, Bulova, Sinn, etc. Wear whatever you want casually, and there are plenty of ways to wear divers with suits IMO. Just don’t wear your G Shock formally – I only wear mine for working out.

    • Barron on

      Great points, all of them! Love that we have a watch nerd in the house. I’m a casual observer of watch forums and Instagram accounts, still figuring out what it is I like in the watches I want to (someday) own.

      I agree you can wear divers with suits, but for the sake of drawing a line (which some readers need), I suggested to stay away. In my comment above to Sean, I mentioned that, save for a traditionally formal / business environment, you can wear almost anything (save for the G-Shock, like you said).

      Thanks for the comment.

      • Andy Budnik on

        Keep up the great work. Glad to see watch articles on here! I enjoy reading up and managed to get rid of 75% of my wardrobe! Unfortunately, or fortunately, I’ve been able to replenish about 50% of that. Still cut down, but loving the fact that I’ve got stuff to wear any time and it all fits, which was a huge bugaboo before. Still too many clothes, but it’s a constant work in progress. But I have this site to thank for getting me on track.

    • John Mercant on

      What do you think about wearing this particular watch with a dressy outfit? (shirt, tie and dress pants)
      Casio GWM5610.

      • Andy Budnik on

        As with anything, totally up to you and your style. I work as a financial advisor, so everyday is a suit and tie. I don’t ever wear my G Shock with a suit- but I bought it for working out and outdoor activities. I’ve seen it done as with smart watches and some louder straps (yellow/orange) and I personally think it detracts from the rest of the outfit. Being that it’s smaller and not as loud, I don’t think you’d have any issues as long as you like it. We read this to get ideas and there are “standards,” but I feel like 80% of people don’t notice anyway. and about 5% of those that do will care about the actual watch with any snobbery. Wear what you like and are comfortable in.

  3. Sean on

    What recommendation would you give to someone on a limited budget and how do smart watches (e.g., Pebble or Apple Watch) factor into the equation?

    • Barron on

      Smart watches would certainly fall under the casual category. If you work in an environment that’s strictly business formal, I personally would choose a traditional, formal watch to pair with my suit. It may not matter so much if you’re in a business casual setting, wearing sport coats with denim, or wearing suits casually, etc.

    • Andy Budnik on

      Sean, on a limited budget, I can’t say it enough, look at Seiko. So much value for the money in every price point. There’s something for everyone there from $50 to $5,000. Seiko 5s are a nice start under $100 in automatic. Their solar models are great too. Their divers are heralded at all price points. Lots and lots of choices. I dislike “fashion” brands that don’t strictly make watches (ie AX that makes clothes, etc), since in my experience, they have not lived up to their price tag in durability or longevity. And I still don’t see a point in smart watches…plus they look geeky to me. Stick to a white face, stainless steel watch with stick indices. Buy it on a bracelet and buy two aftermarket straps – DeBeers and Clockwork Synergy have been awesome and inexpensive on Amazon for me. You have one watch, three ways to wear it. When in doubt, spend a tad more for the watch you really want, or fall down the rabbit hole of buying too many cheapies that add up to more than the watch you wanted, but wouldn’t pay for all at once.

  4. Divyansh Gupta on

    Hello Andy
    I am a college student and mostly wear casual and semi formal outfits. My budget is around $150.
    I am confused whether i should buy a Casio Gshock like G397 or Casio edifice like EF-540D-1AVDF.
    I think that metal strap will not go with outfit that i wear. Is there anything you could suggest me ?