One Watch Every Man Should Own

Note: This post is made possible by The Fifth Watches. If you want to learn more about this brand, check out my The Fifth Watches review.

Classic Brown Leather Watch

Some men truly believe that no outfit is complete without a wrist watch. I respectfully disagree.

I only own a few watches – none of which cost more than $200 – and I don't wear one everyday.

But I do think every man should own at least one watch. And if you could only choose one, it would be wise to go with something simple, classic and timeless.

Gentlemen, I'm talking about the plain face, leather strap dress watch.

Plain face brown leather watch

The Fifth Wwatches Tribeca

Like Taylor Swift, this watch isn't going out of style anytime soon.

You can opt for black or brown leather. It kind of depends on your shoe and belt collection, since it's always good to match your watch, shoes and belt.

But for most guys, a brown leather watch will be the most versatile choice. In fact, you can almost get away with owning one watch if it's the right one.

The great thing about a simple watch with a brown leather strap and clean white face is that it looks good dressed up or down.

Pair it with a suit, and it looks like a dress watch. Pair it with jeans and a button up, and it's a sleek addition to a smart casual getup.

I recommend going with something a bit dressier, rather than opting for a more casual watch. A dressier watch won't look too out of place with a casual outfit, but a casual watch can ruin an otherwise formal look.

A great example of a versatile brown leather strap watch is the Tribeca from The Fifth Watches “New York Classic” collection:

TFW Tribeca watch

This particular watch also comes with a black strap, which is a nice bonus:

Brown and black watch straps

Black or brown leather watch strap

But it's the size (41mm diameter, 6mm depth) and simplicity of this watch that makes it easy to wear with a variety of different outfits.

Note: I prefer gold metal on my watches because most of my belts have gold buckles. If you prefer silver, that's fine too!

To give you some ideas for how to wear this watch, I've put together three different outfits.

Outfit #1: Cold Weather Casual

When to Wear: Guys night out, casual Friday, dinner and a movie

Brown leather watch casual outfit

coat | shirt (similar) | jeans | boots

gloves | earmuffs | watch

You could go with black instead of brown here – black gloves, belt, boots and watch. But most men already own plenty of brown leather accessories.

Let's take things up a notch on the dress code scale…

Outfit #2: Business Casual

When to Wear: Office, church, Thanksgiving dinner

Brown leather watch business casual outfit

coat | sweater | shirt | trousers


First off, a camel topcoat is a timeless and classy way to differentiate yourself from everyone wearing navy, black and grey outerwear.

Second, if you don't have a pair of grey flannel trousers, get on that!

Last, but not least, brown leather ankle boots are just as versatile as a brown leather watch.

I know what you're thinking: “Will this watch work with a suit?” Heck yes it will!

Outfit #3: Suit Up

When to Wear: Office party, wine tasting, any other time where you feel like balling uncontrollably

Brown leather watch dressy outfit

suit (similar) | shirt | watch | shoes

This getup exudes that old school cool. The brown and gold and pale blue are just the right amount of retro.

In this case, the gold watch face is a great choice. It helps bring out the pale yellow tones of the jacket buttons, belt buckle, pocket square and shirt pattern. Silver would make this outfit less cohesive.

Buying a Watch

You can spend as little or much as you want on a classic leather band watch. You can also spend way too much researching different options.

To save you some time, here's a short list of TMM-approved classic watches (in order from cheapest to most expensive):

Regardless of how much you spend, a classic leather strap dress watch will be one of the most versatile accessories you ever buy.

It's worth the investment, no matter how big!

Do you own a classic dress watch? Tell me about it in the comments below!

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  1. Make sure the casing is small 36 or 38 mm at most. .. it’s all about proportions

    • True, but it’s important to remember that not all short men have small wrists. I’ve met 5’5″ guys who have huge arms and hands. For them, a 36mm face would look comically small.

  2. Firstly, I wear a watch every day. I have one that I really love and depending on what else I’m wearing I’ll wear either the black or brown leather band.
    I know that personally, I have a small collection of watches. As a 5’8″ 21 year old male, weighing in at 155-160lbs depending on the day. 40mm is my ideal size.. 36mm feels like a miniature version (to me), 38mm feels good but a little small 42mm is a little too big and makes me feel self conscious. But my-oh-my does 40mm feel and look just right. As for a range 39-41 is good for me.
    BTW: I love watches.

    Disclaimer: I am giving my opinion of what watch works best for me and my wrist. You and your wrist may have a completely different story, so feel free to agree or disagree with me and my wrist.

    • Yeah I think 40mm is a very comfortable size for the vast majority of men. I’m comfortable in a 38mm, and 42 feels too big.

      But you can’t overlook depth either. Huge difference between a thin 40mm and a bulky 38mm.

  3. James G. M. says:

    This is something I keep meaning to get but every time I start looking around and researching – it just gets overwhelming and I can’t man up and commit to one particular model/style.

    Thanks for cutting out the signal from the noise – love the options you presented (especially the Frederique Constant).

    • I hear ya…there are SO many options. Even just Amazon has thousands to choose from. It’s easy to spend hours researching and not make a decision.

  4. Take a look at this Citizen. Almost perfect dimensions for smaller dudes at 35mm diam and 7mm thick. Great brand as well and just slightly cheaper than The Fifth.

  5. Brock, I believe in certain business settings (law and accounting come to mind right away), a classic watch is an essential part of one’s wardrobe.

    I was fortunate enough to be in Hong Kong years ago and buy an authentic Rolex gold and stainless steel bracelet watch, which still keeps perfect time today.

    I am certainly not suggesting that one needs to buy a Rolex or similar expensive watch, as I have found that any classic, well-designed watch works fine with one’s wardrobe.

  6. Brock, while I agree that leather straps and a timeless face define classic styling, the Rolex bracelet watch I mentioned is certainly not over the top in a business setting.

  7. I am seldom without a wrist watch; dating way back to my Air Force days when having an accurate timepiece was vital. Today, I consider a watch, wedding and/or school ring the only suitable jewelry for a man to wear (just me).

    When assembling a wardrobe, why would you limit yourself to “one” of any accessory? One belt? One pair of shoes? One tie. One dress shirt? One suit coat…

    You wouldn’t; and a man need not go severely into debt to have a respectable assortment of watches to match any circumstance. For the price of the watch you are recommending ($150 USD), one could pick from any one of a number of affordable brands (Casio, Bulova, Timex, e.g.) and have a modest collection consisting of one of each: dress watch, sport watch, rugged outdoors watch, and lastly, that old standby—a “beater” to wear when you’re mowing the lawn, cleaning gutters, washing the car, etc.

    Plus, the Fifth Watch at 41 mm, may be oversized for many who subscribe to this blog.

    • Jim, thanks for sharing. Of course I wouldn’t say you should limit yourself to one watch. My point is, if you had to pick one (or start somewhere), a leather dress watch is a good choice.

      It’s like saying a pair of brown lace ups is a good choice for a versatile shoe. Im’ not implying that you don’t want/need more options.

      As far as price goes, it’s just so subjective. Many men (see Randy’s comment) prefer to spend more on a luxury watch. Others want the most affordable option they can find.

      In the world of watches, $150 is considered very affordable. But it’s still a luxury item, and for many men $150 is a lot of money.

      Same goes for size: it’s completely subjective. That’s why I hesitate to say things like “short men should only wear 38mm watches”. That’s not true for all short men. I think you’re right that there’s a loose correlation between height and wrist size, kind of like there is for height and shoe size. But I can’t make broad generalizations based on that.

      Anyway, I ramble. Thanks for your comment!

  8. Fernand cano says:

    Hey Brock! Would you recommend banana republic mid season jackets ( like bombers, quilted jackets…) for a man that is 5’6 and 130 lbs ?

  9. Fantastic options Brock!

    I agree about the diameter, most guys should be okay with something between 38mm and 40mm.

    Another great option for guys is the Timex Weekender. Probably one of the most versatile watches out there for under $50. While you definitely don’t want to wear it with a nice suit, it’s a great watch for practically every other occasion. Also, you can change out the strap just as easily. If you go with a Weekender I highly recommend picking up a James Bond NATO strap from Amazon. Sure, it won’t turn into a Rolex, but it’s a nice way to pay a little homage to one of the most stylish characters in movie history.

    Keep up the great work!


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