The RIGHT Watch to Wear with Your Outfits (Casual to Formal)

For us and many of our readers, watches help elevate one’s style and personality but simply putting one on doesn’t cut it. There is a time and place for different styles of the watch, and today, we’ll help you identify if the watch that you’re wearing is fit for the occasion.

If you’re anything like me, chances are you really like watches. The problem is: once you have more than one watch in your collection, then you have to answer the question: Which watch do I wear? This can be a frustrating question as you have to figure out whether or not the watch is too smart or too laid back for your outfit.

Ultimately, with things being more casual these days, it becomes far easier to wear different watches with different outfits. But – surprise, surprise – here at the Gentleman’s Gazette, we think there’s a way that you can make your outfits look more refined and more coherent.

What Watch To Wear Across Different Formalities

In this guide, we focus on choosing the right watch for different formalities of dress. And don’t worry, if you need a refresher on different types of dress and dress codes, we have a guide for that.

1. Casual

Let’s start on the casual end of the spectrum and work our way up. Who doesn’t love to wind down and relax? Maybe it’s a family barbecue or that much-needed beach vacation. Whatever it is, the goal is to create a chilled-out, off-the-clock look. What that means is that you mostly want to skip the dress watch here.

Elegant designs and minimal details are just too jarring for this look and they won’t mesh together well. Instead, choose a watch with practicality at the center of its design. Sports watches, which boast water resistance, are most ideal here as you can put them on and forget about them.

As I’ve said before, I don’t want to mix my Omega Speedmaster with water – that’s why, for these outfits, when I’m laying by the pool or on the beach, I’ll choose this Omega Seamaster. 

Dressing down is a great opportunity to indulge in watches that are just way too casual for formal occasions. After all, if you’re out hiking or setting up a tent, the last thing you want to worry about is damaging your Patek Philippe Calatrava. Instead, keep those dressy pieces safe and opt for a more rugged utilitarian watch like the Omega Seamaster, maybe a G-Shock, or a Rolex Submariner.

Casual clothing also allows you to economize when it comes to picking the watch to wear. This is especially true when you’re in situations where your watch might get dinged or scratched up. In these cases, you really can’t go wrong with everyone’s favorite digital watch: the Casio G-Shock. At around 100 bucks, the G-Shock can really take any punishment that you give it and, if you somehow break it, you won’t be out that much money.

2. Smart Casual/Semi-Casual /Everyday

Ultimately, we’re all different so your casual clothing might look different than mine, but we’re aiming for that comfortable middle ground. Clothes in the everyday category might overlap with your casual clothes, but it allows you to intermix more casual and more formal items.

Think of combinations like khakis, a T-shirt, and a cardigan; or Chelsea boots, chinos, and a casual jacket. And there’s always the tried-and-true utilitarian OCBD shirt with really any pair of pants.

As you can see, watches from the previous casual category are right at home here. So, feel free to use them interchangeably between your casual and everyday attire.

However, variety is the spice of life, so let’s help you intermix some other pieces. In order for things to work in this category, let’s start refining some of the watch details, but that doesn’t mean you have to jump all the way to your formal watches in this category.

A perfect example of getting the balance right here is my Omega Speedmaster, which I just mentioned I didn’t want to wear at the pool. It has function written all over it as it’s a chronograph with three subdials.

This particular dial layout means that the Speedmaster isn’t for the most dressy of occasions, but the refinement of the simple black and white dial means that it can be a little bit dressier than some of the other watches that we’ve seen – plus it looks great on a variety of straps. And while we’re talking about straps, don’t underestimate the difference in how they can make your watch look.

In this everyday category, you really have the option to play around with different straps. Whether it’s a metal bracelet, traditional leather, or a classic nato design, this is the dress code that will allow you to get the greatest freedom when it comes to your strap choices. You can really elevate your wristwatch game by making smart choices when it comes to these straps.

If you’re looking for a metal bracelet, look for classic options like the oyster, the beads of rice, or the jubilee. It’s an absolutely timeless design and it’ll look great with a lot of watches.

Should leather be more your thing, I would stick away from shiny leathers and choose a waxed, distressed, or suede strap.

And always, a nato strap can be a quick way to give your everyday watch a new lease on life. Try to stay away from overly bright colors and instead choose classic colors and patterns. You can’t go wrong with a navy and white stripe.

3. Business Casual

The next step up the formality ladder is business casual. This is perhaps the most recognized business dress code in the 21st century, and this also might be the most formal that men dress up nowadays. In this category, some of those more casual watches should probably be left in the watch box.

This dress code calls for sharper strap options to be chosen. You can start adding in more refined leathers like oxblood cordovan to match with your loafers. No matter what strap you choose, the focus for this category should be watches that are more streamlined in their features.

As we’ve previously discussed, the Omega Speedmaster would fit right at home in this category due to its refined details, but you could pick other dressier sports watches like the Rolex Submariner or a GP Laureato. 

Another great example in the lower price tier would be the Seiko Presage Series. These are perhaps best known for the cocktail dials, but they come in a wide variety of colors and features. This watch also looks great in business casual attire because it looks great on a strap as well as a bracelet.

Another great watch to consider in this category is the Cartier Tank. This is an iconic piece of watchmaking history. Needless to say, its clean designs and minimal dial tick all the boxes that we’re looking for here.

4. Business Wear

We’ll take another step up the ladder and we are now comfortably within business wear. Think of two and three-piece suits and all the trimmings that go with it. The outfits here all literally mean business even if you aren’t wearing them to work.

Weddings, celebrations, and religious ceremonies all see you dressing your best and upping your style. And if you wear a suit just to dress up daily, you’re among friends here. The watches you choose for this formality are certainly more on the dressy side. And while some of the watches in business casual will be perfectly fine here, there are some details we still want to take care of. 

Take the Seiko Presage from our last example. This watch would be absolutely fine here, but take it off the metal bracelet and put it on a leather strap. The leather is not only more formal, but it can also create a coherent look with your belt, your shoes, and your bag.

The Cartier Tank, JLC Reverso, and a Zenith Captain are all great examples of watches that can transition between these two categories with ease. And if you’re looking for a watch that looks killer with a suit, this Breguet is one to watch out for.

You might not have the budget to drop the money on a Breguet, so if you’re looking for another watch, check out the Timex Marlin. With prices around $200-$300, this is a great vintage-looking piece to add to your outfit. Much like the Breguet, the simple dial and design, it makes it easy to pair with outfits.

5. Black and White Tie

Finally, we have reached the pinnacle of dressing, which is Black and White Tie ensembles. So, what watch should be worn here? Well, it might surprise you but you shouldn’t wear one.

Traditionally, wearing a watch with your evening attire was seen as poor etiquette. Essentially, your presence and, therefore, your attention has been requested at this event, so wearing a watch would make it seem like you’re not fully invested where you are. Rather, you’ll be checking the time to see when you can leave.

We, of all places, have you covered when it comes to the history of these dress codes. In our guides, you will find out about the history of evening wear and how its attitude around the timepiece has evolved. Needless to say, times have changed and White Tie is not an ensemble we will find ourselves in quite often.

Therefore, if you’re putting together a White Tie ensemble, I would recommend going with the “no visible watch” rule. The keyword here is “visible” and so if you’re going to keep a watch with you, best to keep it discreet.

This makes for the perfect opportunity to indulge in a pocket watch. Just make sure that as you keep it in your pocket, it’s slim so as not to be seen. And if you do need to check the time, make sure to ask to be excused and do so privately.

Turning our attention to Black Tie, this is an ensemble you will be in more frequently as it’s commonly used for celebrations. Most people will wear this ensemble on their wedding day, for a friend’s wedding, or maybe a new year’s or Christmas party. So, as Black Tie is a little bit more forgiving than White Tie, it’s okay to add a timepiece into this ensemble.

So, assuming you’re following the classic style guidelines for Black Tie outfits, the watch needs to be very minimal, sleek, and very elegant. Go for something slim with a subtle face. Definitely no oversized monstrosities. And while we’re at it, on the watch dial, minimal is key just. Like the rest of your ensemble, you want the dial to be minimal and elegant.

Also, as a general rule of thumb, you want to keep your metals harmonious. If your shirt studs and cufflinks match, it’s best to tie in the watch as well.

Moreover, where you can wear a shiny black strap as it will tie in well with your evening footwear. My personal favorites are black, shiny crocodile and alligator, which look really elegant. The ultimate goal with your watch in your outfit is to create a harmonious look.

Conclusion

It’s our hope that we’ve been able to guide and inspire you to put together great outfits with your watches.

Do you have any tips or questions about styling watches with outfits? Leave them in the comments below.

Outfit Rundown

Today, I am wearing something comfortably in the everyday category. I’m wearing a gray chunky commando-style sweater. It’s from L.L. Bean, and it’s inspired by some of the sweaters that Commander James Bond wears. I’m wearing slim dark jeans; a pair of dark brown Chelsea boots with our Fort Belvedere shadow-stripe socks in brown.

The watch I’ve chosen is one to dress up my outfit. It’s on a beautiful gray strap and it’s a Zenith Captain. It features a really nice offset seconds hand and a moon phase, which really makes the outfit dressed up.

If you like these socks or any of the other Fort Belvedere products, go ahead and check out our shop.

A note that our good friends over at Delray Watch sent along many of the watches we’ve featured here, but this post is 100% not sponsored.