How To Wear a Watch With a Dress Shirt

If you’re unsure about how to wear a watch with a dress shirt, here’s the proper etiquette.

You don’t need to be going to some white-collar job to wear a dress shirt. It’s actually a great way to level up a casual outfit. Simply replace the t-shirt in that t-shirt, jeans, and sneakers combo with a good button-up. Your look will go from pub-hopping with the guys to date night-appropriate.

If you aren’t used to wearing dress shirts, though, that area by your left wrist bone might be tough to navigate. You know the area I’m talking about — the one where your wristwatch goes. 

(And yes, it’s your right wrist bone if you’re left-handed).

Should it bump the shirt cuff or go over it? Under it, perhaps? No worries. Here’s everything you need to know regarding how to wear a watch, any type of watch, with a dress shirt.

Dress Watches With Dress Shirts: A Rule of Thumb

Traditionally, your watch should be able to go under your shirt sleeve. Some say that it should stay under there until you flick your wrist and fold your arm to look at the time. 

However, th4se days most would agree that it’s okay for it to peak out.

Regardless of what camp you fall into, do not wear it over the cuff. Even in today’s no-rules, avant-garde, anti-fashion fashion world, I can’t think of a context in which that would be appropriate.

Now that being the case, your watch’s strap needs to fit firmly around your wrist. It’s not just a bracelet, and therefore shouldn’t move. 

The watch case should sit in the middle of your wrist, with the lugs never going past your wrist bone.

Relatedly, too tight is better than too loose — comfort willing.

Some women’s watches feature a decorative back clasp that she can wear on her front wrist, with the watch face on her back wrist. This “feminine” way of brandishing one’s watch was designed so that ladies didn’t have to make the “masculine” gesture of folding one’s arm.

Ironically, wearing watches upside down started with men in the military who wanted to protect the front dial. These days, it is still more common for women to wear watches this way, but it isn’t a strict rule.

If you’re interested in trying it out, feel free!

You can always just switch it back to the regular composition if you change your mind. Still, all the same rules apply regarding centering it and ensuring it tucks under your sleeve.

I personally wear a 28-millimeter Seamaster as a dress watch, which is technically a ladies’ watch. 

It has a lovely clasp, but I’ve never worn it upside down myself. That’s completely due to my own preference, though.

Sport Watches vs Dress Watches

Alright, what about my big clunky dive watch? Can I wear that with a dress shirt and what if it doesn’t fit under the sleeve?

Thanks to James Bond, dive watches are ubiquitous everyday watches. In fact, the Rolex Submariner is the most recognizable watch in the world. So, many men wear it with their suits to work, and that’s perfectly fine these days.

They’re meant to be worn with casual clothing, though. As mentioned earlier, you can incorporate a dress shirt into a casual combination to create a leveled-up high-low situation.

If you choose to wear any tool watch with a dress shirt, whether that’s a GMT or a field watch, it should still tuck under your sleeve. 

And here’s my controversial opinion. With big tool watches, personally, I’m not that concerned that it tucks under my sleeve at all. Partnering a sports watch with a dress shirt is already, in the strictest sense, unconventional. 

But, as long as it’s not sitting on top of the cuff, and as long as it can tuck into a hypothetical suit jacket or blazer, I think most people wouldn’t really notice.

Again, if you want to play it safe, keep the tuck. This is just what I’ve noticed as someone who spends a lot of time in the watch industry, with watch collectors, and around watches.

You can also always fold your sleeves, eliminating the question altogether.

With formal watches, there’s less wiggle room. Follow the aforementioned rule. It should sit on the middle of your wrist, above your wrist bone, and it should tuck in at least halfway.

What About Formal Events?

Here are some things to consider if you’re going to a formal event.

First off, traditionally, a formal dress watch should be on a black leather strap. 

These days, you can wear formal watches with metal straps, too, especially if it’s precious metal. Just make sure it’s either simple and understated or something dressy and jewelry-like, like a Milanese bracelet.

Secondly, you might be considering wearing a sports watch to a formal event. I know Connery’s Bond did that with his Submariner decades ago, but you should still tread carefully, as I do with my ladies’ Omega, of course.

At a black tie event, technically, you don’t have to wear a watch at all. In, again, the strictest sense, one doesn’t wear a watch with a tuxedo because it can be considered rude to check the time on formal occasions.

However, even the most ardent sartorial rule-followers these days will wear a watch with their tuxedo. Some will even wear a sports watch. 

The Prince of Wales, for example, always wears his Seamaster with his tuxedo. And truly, there are no people more bound to sartorial rules than modern royals.

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The style exception that this plays into is that family heirlooms are technically always allowed in formal situations (assuming your family heirloom is tasteful). 

Still, you, and yes, even the Prince of Wales, do have to tread carefully in one very important sense. If you’re at a black tie event and there’s programming that involves the lights dimming, your lume might activate.

Just keep it under your sleeve, or simply take it off and put it in your jacket pocket until the lights come back on. The most important thing about navigating style rules in black tie formals is to be respectful of your hosts and fellow guests.

Conclusion: The Tuck Is Your Safest Bet

When in doubt, just make sure your watch tucks under your cuff and sits on the middle of your wrist, with the lugs not going past your wrist bone.

I know I threw a few nuances and opinions your way. And feel free to experiment with these tips. But know that the most traditional way is always the safest.

Do you ever wear sports watches with dress shirts? How do you ensure it tucks in properly? Some button the cuff loosely, while others simply fold their sleeves up. Which camp do you fall into?