How to Match Watches to Your Outfit

One of the most common questions we are asked about watches is: “how do I match my watch to my outfit?”

Surprisingly, most of the people asking this question aren’t wondering about type of outfit, but more specifics. They know not to wear a dive watch with a suit or a dress watch to the beach. What they are really wondering, is how they match it.

One can argue that matching your watch to your outfit comes down to the band or strap, but there are a few other contributing factors that should really be taken into consideration. For obvious reasons, when you have a small selection of watches to choose from, you can’t be quite as particular about making sure it coincides with the outfit you chose, but there are still some basic considerations that can help ensure your watch-outfit combinations look spot on.

The first rule of thumb when it comes to watches is always less is more. Unless you’re trying to steer attention to your wrist, a watch should really just be an extension of your outfit. The goal is to enhance your outfit rather than stand apart from it. A watch is evidently useful for telling time, however, if it was simply time we were after, our smartphones would be more than suitable. For the true gentleman, wearing a watch is far more than having the tool of time on their wrist. It’s about showcasing personal style and their story. For women who say you can tell a lot by the type of shoes a man wears, the same can be said for a watch. Watches come in all price ranges, but for the purposes of this article, the focus will be on the style and matching of the watch, not how much it costs. No matter the retail price, a watch should enhance and complete your outfit harmoniously.

Just as a man might choose to showcase his style and personality in his shoes or clothing, the watch can prove to be a valuable tool for accessorizing that style — especially since men don’t traditionally wear many accessories, aside from perhaps a wedding band, a hat or glasses.

How To Match Watches To Outfits: The Process

Step One: Determine Your Interest Level in Watches

Let’s start with the obvious: How often do you want to wear a watch? Every day, or do you want a nice watch for specific purposes like the office, evenings out, black tie events, or for sporting? Your interest in watches, in general, will have a big impact on how you match watches to your outfits. If you are only interested in having one watch, then you should start by choosing the dress code you want to pair it with and buy the watch specifically for that purpose. Beyond this one dress code, you won’t be wearing a watch. Your journey will stop here, though we dare say that owning a nice timepiece may encourage your interest in regular watch wearing and you may want to read on.

Alternatively, if there is only one watch that peaks your interest, buy it first and then use the following process to figure out what outfits you can pair it with. That being said, we would recommend the first approach, because otherwise, you could end up with an expensive, attractive dive watch that sits in a drawer because you spend your days in a white collar office. On the other hand, if you like the idea of wearing a watch regularly or even daily, proceed to the next step.

Step Two: Create a Versatile Base Collection of Watches

As mentioned, different watches suit different occasions, and if you would like to be a regular watch wearer, a proper match between your watch and your attire will elevate your look and show that you pay attention to detail. Matching the wrong watch to the wrong outfit will make you look amateurish or worse, like you are trying to show off.

Ideally, a man would want to have five to seven watches in his base collection. This would include the following:

1. A Simple Dress Watch with a Silver Case

Whether it be stainless steel, white gold, silver or rhodium, this watch should have a slim, high-quality leather band. It is useful to have two straps, one brown and the other black, both of which should have a simple finish; it’s best to skip flashy bands such as lizard or alligator which do not suit the understated elegance of a great dress watch.

A dress watch, relative to other watches, is usually smaller with a rectangular or round shaped dial. The dial will be very simplistic with a plain white, cream, gray or even black face.

2. A Second Simple Dress Watch with a Gold or Rose Case

This could be yellow or rose gold, whichever suits your preference but it should match any gold accessories you own such as gold color belt buckles, suspender clasps, cufflinks, shoelace aglets, eyeglasses, rings or pocket accessories (such as a money clip). This watch would also have two bands, the same as the previous dress watch listed above. If a second dress watch isn’t quite in your budget, consider buying a second strap for the dress watch you already have. If the one that comes with it is black, buy one in brown, and vice versa.

3. A Casual or Sports Watch

This watch would have a face with a basic color scheme such as black or navy — not very flamboyant (yellow, red, orange, etc). Ideally, it would have a metal bracelet or a dark strap. This watch should be water resistant and ideally feature any complication the wearer would require (chronograph, etc). For the diving or sport casual watch, a metal bracelet is ideal. Purchasing a second sports or casual watch with a canvas band will extend the versatility of your sports watches to almost any casual outfit.

Casual watches and sport watches are slightly different, and in general they are larger and have more detailed designs than dress watches. The difference between a casual and sport watch is that sport watches are timepieces specifically designed for use during an activity whereas casual watches are designed to be worn with casual or informal attire. A chronograph is a sports watch whereas a watch like the Timex Weekender with a NATO strap would be considered simply a casual watch. Of course, something like the Weekender can also be worn as a dress watch by substituting the casual strap with a fine leather strap. This can also apply to other features, or complications, in that a watch with a helium escape valve would be considered a sports watch because it can be worn diving, however, a similar looking watch without the complication would be a casual wear watch. A good example of this is the Rolex Milgauss which is designed for work wear, but looks similar to the Rolex Submariner which is a diving watch. It comes down to what the watch is intended for. The two types do overlap a bit.

4. A Pocket Watch (Think of it as a dress watch without a band)

Today, many men feel that the pocket watch is too traditional or old fashioned for their tastes. If that’s you, then skip this section, but we would encourage you to read on because a pocket watch can be a strong statement in both a classic and an eclectic sense. These days, a pocket watch — and importantly, the visual chain you wear it with — suits both admirers of classic style and the new hipster interpretations of classic style, so it is a far more versatile piece than many imagine it to be.

However, for those men who do attend formal events, a wrist watch is very inappropriate. If you read my article on wedding watches, you’ll notice it’s become a trend for the bride to give her groom a watch on their wedding or in honor of their engagement. While the gift of a watch at your wedding is very appropriate, what isn’t is to wear a watch to the actual event. Any time where you need to be focused on the event itself without regard for your schedule should mean leaving your watch behind. Glancing at your wrist shows others that you have other things on your mind and that their presence isn’t your priority. In other words, determine whether time or the event is of more importance. If it’s the event, than leave the watch off your wrist. This is where a pocket watch can come in. Aside from being a fantastic family heirloom, the pocket watch is discreet and formal enough to be hidden in the pocket of your vest, jacket or trousers. If you feel the necessity to check the time, you can excuse yourself to a more secluded space such as the restroom to check the time. Traditionally, not wearing a watch really only applies to formal events, but seeing men checking their watch while on a date, at a restaurant or any other event where your focus should be on the people you’re with is a breach of even modern etiquette.

5. A Personal Timepiece

This could be another dress watch, a diving watch, flight watch, or any other watch you want. This is the watch that really showcase your personal style. There are no limitations! This is a watch you probably just saw and fell in love with. It’s worn when your clothes happen to all fall into place and match it perfectly. You don’t generally force it on your outfit, but will use it to accentuate the outfit whenever possible.

Any watch thereafter is really just an addition to your collection. Some men will buy a more expensive version they previously couldn’t afford and use it as a replacement for a cheaper watch, whereas other men will just add it to their collection and wear it in addition to watches already owned. I personally do both, except I rarely dispose of a watch. In most cases, if I tire of a watch or have one that I want to replace, it then gets handed down to my son or given to a friend.

This Omega Speedmaster watch may have a black leather band, but it is not suitable for black tie

Step Three: Match the Watch to the Dress Code

The dress code or situation in which you wear the watch should be the primary factor in determining how to match a watch to your outfit because it will also dictate the clothes you choose. Start first with your outfit,and select each item that you intend to wear with it, including socks, shoes, and cufflinks, so that your combination is appropriate for the environment you’ll be in. As a rule of thumb, if you are wearing a jacket of some kind, you should reach for a dress watch first.

When to wear a dress watch: in a white collar office, a business casual office, at an important client meeting, at a wedding, at a garden party, with black tie, at a charity event, at an elegant restaurant, to the orchestra or theater, or golfing with colleagues or clients (most golf clubs have dress codes).

When to wear a casual/sports/dive watch: to a backyard barbeque, to a bonfire, sailing, biking, or other sporting events as a participant or a spectator, to a business casual office, to happy hour with friends, to casual restaurants, shopping, or a casual golf outing with friends.

Step Four: Match Your Metals, Face Color and Band to Your Other Accessories

Finally, you need to match the metal, face color and band of your watch to your outfit. Match a watch with a metal case or band to outfits that contain other metal elements of the same color, such as your belt buckle, shoe buckles, tie bar, pinky ring, collar bar, or cufflinks. The exception to the rule is a wedding band, which can be worn in the opposite color because it is something most men do not remove or change depending on the dress code.

Next, match the watch band, if you are wearing a leather band, to the other leather in your outfit — your belt and shoes. Brown bands go with brown shoes and belts, and black bands go with black belts and shoes.

The next step is to look at the color of the watch face. Typically lighter (cream, white, etc) faces are for day wear, whereas a darker face (black, grey, mocha) are for evening wear. Ideally, you want to try to and match these as best as possible to your outfit, the activity and the time of day. Obviously, this can be a very important contributing factor if you own watches with colored faces such as a red or yellow. A watch with a bright yellow face can match perfectly with a casual outfit accented by yellow shoes or a yellow belt.

Watch Matching DON’Ts

Finally, there are some key mistakes to avoid when matching watches. If the above represents the “DOs”, then here are the things to avoid.

• DON’T consider a smart watch a “watch”. It’s not — it’s an extension of your phone that you wear on your wrist, and we have yet to see a smart watch that is slim and stylish enough to be considered a true wardrobe accessory. In fact, smart watches (aside from being generally unattractive) only enhance the social problems created by cell phones. As a constant presence on your wrist, they are a distraction that is more likely to make you look rude than attentive to your work. If you must wear one, avoid checking it during in-person interactions. Leave it at home for social occasions as nothing says “I’m not interested in you” more than someone checking an email mid-conversation at 8pm on a Saturday.
• DON’T wear a dress watch in any situation in which it can get wet. They are not intended to resist the elements. Sailing, sporting, diving and swimming are all activities that demand a sports or casual watch, which are almost always water-resistant.
• DON’T wear anything other than a dress watch with black tie. We know, James Bond wears an Omega dive watch, but he’s a spy who may, in fact, get wet wearing a tuxedo. Furthermore, watch brand endorsement deals are happy to benefit from Bond wearing their watch when he looks his best, even if it breaks the rules.

Conclusion

Wearing your watch as an accessory to your outfit can be daring, challenging and fun. Often people can judge how style-savvy you are by your smaller accessories. Wearing that brown strap with black shoes or a black belt can really make you look out of place. While you may have a favorite watch in your collection, it doesn’t mean it has to be worn all the time. After all, every watch you own should be one you like, so rotate them and place some importance on how well they coordinate with not only your outfit, but also the activity you’re engaging in.