There are an overwhelming number of stunning watches to pair with your outfit; how can you possibly know where to start?

Thankfully, watch shopping doesn’t mean you simply need to pick the one you like best. (That would be too difficult!)

The choice for the right watch starts long before you even begin shopping. It all starts with your personal style and how you already dress each day.

Understanding the Different Types of Watches

There are several different types of watches, which can be an incredibly helpful way to start your search for the right watch.

different watch types infographic

Understanding how you’ll incorporate your watch into your outfit (whether for work or leisure) provides a clear direction in choosing the one that suits you best.

It’s also a good idea to know ahead of time just how interested you are in wearing a timepiece. Watches aren’t for everyone; some men just aren’t the type.

And that’s fine, but you should recognize if that’s the case before you drop a wad of money on an expensive watch.

Once you determine how you’ll be wearing your watch, you can steer toward one of these categories:

  • Dress watch – very simple and usually reserved for suits and tuxedos. Dress watches generally have a clean face, with only numbers and hands. Identifiable by its black leather band.
  • Diver’s watch – more of a worker watch and match most outfits. These heavy-duty timepieces have a metal bracelet and are not considered dressy.
  • Chrono watches – Although very sleek, they are typically made with a plastic or rubber band. Still, they can look very nice and are semi-dressy. It’s a type of watch you can match with almost any outfit.
  • Pilot watch – Defined by its huge face with matching large dials. It also includes several complications. They bring an adventurous vibe to an outfit and usually fit best with business-casual or smart casual attire.
  • Field watch – Originally a military watch, this durable and very reliable watch makes a strong statement. They often pair best with casual or smart-casual outfits.

The Formality of the Watch Has to Match the Formality of Your Outfit

Sure, your watch is a helpful device, but also an accessory. Make the wrong choice, and your fashion may suffer.

what to wear by dress code

It’s essential to draw people’s eyes to you for the right reasons, not a fashion faux pas. Your watch should add to your ensemble, not detract from it.

For example, don’t pair a functional work watch with your black tie dress; the two occasions do not mix.

The Perfect Watch for Black-Tie Events

For your most formal dressing needs, you want a sleek watch with a simple design. You’ll be wearing a tuxedo, so matching a dress watch with it is almost a rule.

how to wear a dress watch with a blue tuxedo

Beautiful and streamlined are the words that best describe dress watches. A leather strap is essential for the highest formality.

Dress watches follow a minimalist style. They don’t have special features, only a small face with numbers and hands.

You’ll notice that dress watches must have a very slim profile; they should seamlessly slip under the cuff of your dress shirt.

And just because you are dressing fancy, don’t get fooled into believing your watch should be flashy. Flashy does not equal fancy, so don’t choose something with tons of gemstones.

A perfect watch for your black-tie needs is a Cartier Tank Solo. It’s the epitome of a dress watch. It’s timeless in its narrow simplicity and iconic rectangular face.

On the different side of the price spectrum, some excellent affordable dress watches might be Timex or Seiko SUP880.

Match Watch for Formal Business Outfit

Choosing a watch for your suit is similar to what you would need for the formal dress but with slightly more wiggle room.

Hublot Big Bang with a formal business suit

For example, you can decide between a leather or metal watch band.

Your business watch should still be light on the complications; too much “busyness” doesn’t look business-professional. Again, the path to elegance is simplicity.

Adding a watch to your business outfit sends a good message. It indicates your attention to detail and level of responsibility.

To display your business prowess, opt for a unique watch like Hublot. This choice of luxury watch showcases your impeccable taste. Hublot watches are available in many styles, but opt for a simple and modern design.

Pairing Watches with Semi-Formal Outfits

Semi-formal dress maintains a level of dressiness but certainly loosens up the rules. You’re still required to wear a suit, and shirts and ties are warmly recommended.

Rolex Datejust with a semi-formal blue suit

The same can go for your watch on semi-formal occasions.

You could just go with a dress watch, but this is also a chance to branch out and embrace something that may have a bit more personality, like Chrono or a Diver watch.

Semi-formal is not a stressful dress code to follow. You need to look nice but can be much less strict when dressing.

So think of your watch in similar terms; you can be more flexible with materials and designs. Feel free to add in some complications and perhaps even some unusual colors.

Consider a unique and beautiful watch like Rolex or the Omega Seamaster. If you’re looking for a more affordable option, Citizen Eco-Drive or Fossil The Minimalist might be some great options.

Matching Watches with Business Casual Outfits

Here’s where you can really begin to steer into more firmly casual territory. For example, you’re welcome to start to go a bit bulkier now, like with a dive watch.

Tag Heuer Autavia Calibre 5 with a business-casual outfit

You can also begin to add a few more complications to your watch, like a calendar.

A leather band may feel too constricting for your business casual style. This is the ideal time to look at metal watch bands; Chrono, pilot, or field watches work perfectly here.

The TAG Heuer Autavia Calibre 5 chronometer watch is a beautiful choice for business casual outfits. It is sleek enough to be seen as professional but not bland at all.

Watches for Smart-Casual Outfits

A smart-casual style blends trendy and semi-formal with comfort. It’s the perfect way to be informal but without sliding into sloppiness.

Patek Philippe Nautilus watch with a smart-casual outfit

You can use your watch to contribute to your outfit’s relaxed feel.

Think about dressing in blazers, chinos, and button-down dress shirts. A sleek formal watch may feel overdone, so look toward aviator, field, or chrono watches instead.

Patek Philippe Nautilus is an excellent choice to bring a classy and elegant style watch to your wrist. Or check out AX Armani Exchange for a more affordable option.

Sport Watches for Athletic Wear

When you wear a watch with your sports outfits, your focus should be more on durability and not so much on style.

Garmin forefunner for athletic wear

A watch worn during games needs to be able to take a beating. Leather and metal bands aren’t likely to be comfortable for these occasions, either, so rubber or plastic should be the name of the game.

Naturally, this style will be very casual. Your watch doesn’t need to actually be sporty, but it should be lightweight and water-resistant, at the very least.

A Garmin smartwatch is an ideal example of a watch for athletic wear. It’s an attractive watch that can keep you connected to your music and friends while tracking your stats.

Leather Straps on the Watch & Outfit Leather Should Match

This age-old guidance is much less of a rule these days and more of a friendly tip.

matching brown dress watch with brown shoes and a brown belt

There was a time when mixing leather color was completely non-negotiable, but this is relaxing a bit these days.

Still, it’s a healthy rule to follow when possible. People will look twice at mismatched leather.

This is most essential with leather on your belt and your shoes. These are the leather items that stand out the most on your outfit, so do your best to focus on those areas.

At the very least, try to ensure the colors are in the same ballpark, even if they are different shades.

Metal Straps on the Watch & Other Outfit Accessories Also Should Match

Here’s another rule that isn’t hard and fast but definitely worth following wherever possible. This is a “should” rather than a “must.”

how to match the metal watch with the rest of your outfit

Metals come in such a wide range that matching them can often be more complicated than it is to match leather.

So at the very least, aim for “close enough.” For example, stainless steel paired with silver isn’t the end of the world, nor is gold with rose gold.

Don’t forget to take stock of all the metal you’re wearing with your outfit. Look at your ring, cufflinks, and even your belt buckle.

Be sure that you aren’t wearing three glaringly different metals from your watch band!

The Watch Strap Complement the Shoe

Matching leather to leather is one thing, but what about how to match leather to metal? Is there some sort of color scheme worth considering? Yes, there is!

match watch color and leather with shoes

Some metals just look better with specific leather shades.

Warm and cool tones certainly play into all color schemes, even when the materials are drastically different.

Silver looks best against dark neutral shades, like black, blue, and grey. Gold is an earthy hue, so it pairs best with earth tones, like all shades of brown.

Family Traditions Supersede Fashion & Trends

Do you have an old timepiece handed down from a family member? These accessories aren’t about fashion.

Instead, they stand for tradition. So feel comfortable wearing it without worrying about style trends and rules.

family heirloom

These pieces are unique and send a different kind of message.

For instance, it’s usually apparent that an heirloom watch wasn’t recently purchased. Its older flavor can replace any style rules that are currently in place.

As long as you aren’t wearing a formal timepiece with your sweatpants, you should be good to match it any way you please.

Less is More

Fashion is never about piling on as much as possible. Restraint is a golden word in almost all areas of dressing well. The same holds true for your watch.

Avoid wearing oversized pieces. A large watch face can be stylistically attractive and functionally appealing, but don’t overdo it.

do not wear oversized watches

And never pair it with a wide watch band. It would be too distracting and look garish.

Skip a lot of bling with your watch. A subtle, tasteful diamond chip on your watch face can look suave.

But a watch face that’s entirely surrounded by diamonds and other gemstones is screaming for attention. And trust me, it won’t be good attention.

And finally, avoid the temptation of adding many complications to your watch. Sure, you can include some very cool complications, but you don’t need them all.

watch case complications

Remember, at the end of the day, this is a tool meant to tell time, not do your taxes.

Alexander Stoicoff

Author: Alexander Stoicoff

Hi, I’m Alex, and I’ve studied and specialized in styling in Rome. Through my writing, I want to help men dress well and learn the purpose and significance of suits and other formal attire. My final goal is to make men more confident in their wardrobe choice and life in general.