When it comes to men’s fashion, a nice watch is so much more than a device to tell the time. Its a statement of style, sophistication, and status and most importantly signifies important memories or milestones in your life.
In this guide, we’re going through how the right watch can elevate your look and make you stand out, going in-depth into the best luxury watches for men, from dress to dive and everything in between.
If you’re looking to start your collection or you’re already a seasoned collector, we know you’ll enjoy this read.
Table of Contents
The Dress Watch
The Rolex Datejust
We’re kicking things off with a true classic that we have no doubt you’ve heard of. The Rolex Datejust.
This iconic watch has graced the wrists of countless gentlemen, the most notable being James Bond, David Beckham and Roger Federer.
With its clean lines, minimalist design, and famous cyclops date window, the Datejust is suitable for all wearers looking for an entry into the luxury watch market.
Pros:
- Classic and timeless design
- High-quality craftsmanship
- Versatile for both formal and casual occasions
- Strong investment prospect
Cons:
- Long waitlist
- Can often require servicing
You can expect to pay around $5,000-$10,000 for a well-conditioned Datejust, with some rarer models exceeding $100,000.
The Jaeger-LeCoultre Master Ultra-Thin
For those who appreciate Swiss craftsmanship and a slim profile, the Jaeger-LeCoultre Master Ultra-Thin is a fantastic choice to add to your classy watch collection. A very similar variation of this watch was worn by Dr Strange in the first instalment of the series, associating it with the elite.
A brand also favoured heavily by Robert Downey Jr., a minimalist dial and ultra-thin case make it perfect for any formal occasion.
Pros:
- Swiss precision and craftsmanship
- Slim and sleek design
- Ideal for formal Wear
Cons:
- Significant investment for limited return
- Limited availability in some regions
Expect to pay around $6,000 for this piece.
The Dive Watch
The Rolex Submariner
No classy men’s watch guide would be complete without the presence of the Rolex Submariner.
Perhaps the most well-known luxury watch model, the Submariner is steeped in history and combines style and durability to become a top contender for any watch bearer. This watch graces the wrists of many notable figures including Roger Federer, Tom Holland, Keanu Reaves and David Beckham.
The legendary diving accessory has been a favourite for decades, with its effortless style, robustness and waterproof capabilities. The perfect choice for both land and sea.
Pros:
- Iconic design with a rugged edge
- High-quality materials and craftsmanship
- Suitable for water-related activities
Cons:
- Prone to counterfeits due to its popularity
Prices for the Submariner typically start at $8,000 and increase from there for the rare or limited-edition models.
You also need to expect a year-long wait for a new model if you have no prior experience purchasing with Rolex.
The Omega Seamaster Professional
The watch of choice for the 007 agent, James Bond pairs his dinner suit with the iconic Omega Seamaster.
The piece is not only functional underwater but also incredibly stylish on the land.
Worth much less than the submariner, the Omega piece is a more affordable entry into sophisticated dive watches. Endorsed by none other than George Clooney, this watch stands as a testament to fine watchmaking
Pros:
- Affordable compared to other luxury dive watches
- Reliable performance underwater
- Stylish and Iconic Design
Cons:
- Limited customisation options
For a new Seamaster, prices start around $4,000, but if you want to get your hands on limited edition items such as the 007 edition, you’ll need to fork out an extra $8,000.
The SmartWatch
The Apple Watch Series 9
Possibly the most practical watch on the planet (if you’re an iPhone user), the Apple Watch easily blends functionality with fashion.
Key Features:
- Health tracking
- Customisable watch faces
- Sleek Design
- 5G connectivity
Perfect for the office or on your morning run, it’s an affordable, but practical choice to add to your watch collection.
Pros:
- Versatility & PRACTICALITY
- Modern
- Customisability
Cons:
- Will not hold value as traditional watches do
- Requires regular software updates
- Monthly subscription for cellular
Prices will vary depending on the model, but you can expect to pay around $400 for the entry model.
The Garmin MARQ Collection
The sporting capabilities of Garmin watches are incredible, with perfect options for aviation, golf and sailing.
From measuring distances to sea currents, these watches have all the functionalities to provide you with expert knowledge, without the single screen look that the Apple watch possesses.
They’re not only packed with features but also boast sophistication.
Pros:
- Tailored for specific activities and sports
- Advances in tracking and navigation features
- Durability
Cons:
- Higher price point than its previous competitor
- Steeper learning curve for less tech-savvy individuals
Expect to pay $1,500 to $2,000 for one of these.
The Pilot Watch
The IWC Pilot’s Watch Mark XVIII
Pilot watches are known for their readability and charm. They need to be simple enough to glance at in the air, yet have the ability to keep time in sometimes over 3 time zones.
This timepiece is a prime example, featuring a classic design inspired by aviation instruments.
If you’re a man of the skies, you need one of these in your classy watch collection. IWC is a renowned brand, featured on the wrist of Taron Egerton and Sterling Kelby Brown at the 2024 Oscars.
Pros:
- Legible and functional design
- Swiss precision
- Ideal for aviation enthusiasts
Cons:
- Limited customisation options
Expect to pay minimum $4,000.
The Breitling Navitimer
Prefer larger watches that hold their elegance? This is a superb choice.
Flair paired with practicality, the piece includes a distinctive slide rule bezel and chronograph function. The perfect companion for any globetrotting gentleman.
Pros:
- Unique and iconic design
- Feature-rich for travellers
- Swiss-made quality
Cons:
- Bulky size may not suit everyone’s wrist
Prices for the Navitimer start at approximately $5,000.
The Tactical/Field Watch
The Luminox Navy Seal Colormark
“Understand tough conditions while remaining stylish.”
That is the criteria that these tactical/field watches must achieve, and the Luminox Navy Seal Colormark does this perfectly.
With its rugged construction and glow-in-the-dark markers, this timepiece is ready to get put to work.
Pros:
- Rugged and durable
- Affordable entry point
- Luminous markers for low-light situations
Cons:
- Less formal in appearance
- Limited versatility for dressier occasions
Prices start at $300, making it an accessible choice to add to your watch collection.
The Hamilton Khaki Field Auto
We’re cutting straight to the chase. We LOVE this watch.
An excellent option combining military-inspired design with Swiss precision. From hands-on practicals in the field to dinner parties, Hamilton covers you for all occasions.
The black dial contrasts perfectly with the silver frame and custom khaki strap, matching a plethora of outfits.
Pros:
- A blend of military and Swiss craftsmanship
- Versatile for casual and outdoor wear
- Accessible price point
- Looks AMAZING with leather jackets
Cons:
- Less formal for dressier events
- Limited customisation options
Expect to pay between $500-$1,000
Bonus Watches: Racing, Digital and Pocket Watches
The TAG Heuer Monaco
We can’t give you a list of the ultimate watch collection without including a TAG Heuer ‘Monaco’.
This model is for those who appreciate the adrenaline rush of racing.
An iconic watch, this square-shaped chronograph was famously worn by Steve McQueen in the film “Le Mans.” and has inspired the future of TAG Heuer Formula 1 watches.
Pros:
- Unique and stylish design
- Associated with motorsports heritage
- Swiss precision and quality
Cons:
- High entry price
- Square shape may not appeal to all tastes
You’ll need at least $6,000 to purchase one of these.
The Casio F-91W
The cheapest watch on this list is worn by one of the wealthiest men in the world.
This black digital watch gained enormous popularity when Bill Gates was photographed wearing the timepiece.
A minimalistic appreciation of the 1989 watch, this watch is perfect if you don’t want to spend big and need a lifetime battery supply.
Pros:
- Extremely cheap
- Timeless classic
- It tells the time!
Cons:
- Frequent servicing
- Cheap materials
These come in at $20, so get moving and add this to your cart!
The Pocket Watch
For a touch of vintage charm, consider a pocket watch.
Made popular again in the 2020s (largely due to Tommy Shelby and The Peaky Blinders) people are scrambling to get their hands on these, and you should be too.
Brands like Patek Philippe and Vacheron Constantin offer exquisite pocket watches that inspire back to the bygone era.
Pros:
- Vintage and nostalgic appeal
- Exceptional craftsmanship and material
- Unique and classic design
Cons:
- Less practical for everyday use
- Maintenance and care may be challenging
Prices for these pieces vary dramatically from $10-$100,000.
Editors Choice
Cartier Tank
A true legend in the luxury watch world, the Cartier tank boasts a distinct rectangular case and minimalist design.
It screams Princess Diana vibes, and we’re here for it.
Cartier tanks have been a symbol of sophistication and refinement for over a century, with many public figures gracing their wrists with this watch. It also fits the ‘old money‘ trend that Succession has brought into the spotlight
Pros:
- Timeless Design
- Brand Prestige
- High-Quality Materials
- Versatility
- Visually STUNNING
- Goes with almost any outfit
Cons:
- Expensive
- Regular Maintenance
- Rectangular shape may be uncomfortable
This classy piece of timekeeping starts around $4,000 and ranges up to $50,000+.
Conclusion
Choosing the right classy men’s watch is a matter of personal style, budget and the intended purpose.
It is all about choosing what you find visually appealing and believe you could gain value from.
Looking to start your collection on a budget? Here are our favourite watches under $2,000 to get you started.