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Best Casual Watches for Men – Your Ultimate Style Guide

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Paul Altieri

These days, there are luxury watches designed for nearly every possible use and environment. From dive watches and pilot watches to racing chronographs and regatta timers, you can find a purpose-built timepiece for just about every imaginable lifestyle and activity. With that in mind, even if you are one of the few people who actually scuba dives or races cars, there will always be those times when you aren’t doing those activities and for those occasions, you may want to have at least a couple of casual watches in your collection. 

Unlike divers, pilot’s watches, or racing chronographs, there is no exact definition of what constitutes a casual watch – other than that it must effortlessly fit into your lifestyle and cannot be either overly formal or intentionally designed for one particular sport or lifestyle activity. However, just because a model is a sport or tool watch, that does not mean that it cannot also be a fantastic timepiece for everyday wear and use, so below are some of the best casual watches for men, including a few sports models that are also worth considering if you are looking for that one watch that you can wear all-day, every day for the rest of your life.

Rolex Air-King 5500

Best Casual Watches for Men Ultimate Style Guide Rolex Air-King 5500

Air-King 5500 Key Features:

– Case Size: 34mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds

– Dial: Multiple Options Available

– Bezel: Fixed, Stainless Steel, Smooth Style

– Crystal: Acrylic

– Movement: Rolex Caliber 1520 or Caliber 1530

– Strap/Bracelet: Oyster Bracelet or Jubilee Bracelet

– Approx. Price (USD): $3,500 – 4,500 (Pre-Owned)

The hallmarks of a really great everyday watch include a comfortable case and bracelet (or strap), a reliable movement, and a dial that is easy to read at-a-glance – just to name a few. The Rolex Air-King 5500 checks all the boxes required of the perfect casual Rolex with an unassuming design, durable steel-on-steel finish, and convenient self-winding movement.

While the reference 5500 is a vintage timepiece that first came to market during the 1950s, it will easily stand the test of time because it’s backed by impeccable Rolex craftsmanship. Regardless of age, the Air-King 5500 will continue to provide reliable readings for many years to come. It is also a wise investment choice on the introductory level because it bears the name Rolex on its dial while maintaining a very affordable price.

The Rolex Air-King ref. 5500 measures 34mm in diameter, which allows it to be incredibly easy to wear. It makes a subtle statement with the iconic Rolex coronet positioned at the 12-hour marker; however, the compact size prevents it from overtaking the wrist. It also slides easily under the cuff of a tight dress shirt and looks just as stylish with jeans and a t-shirt as it does with a tux.

Rolex Day-Date 118139

Best Casual Watches for Men Style Guide Rolex Day-Date Presidential 118139

Day-Date 118139 Key Features:

– Case Size:  36mm

– Materials: 18k White Gold

– Functions: Time w/ Running Seconds, Date Display, Day-Display

– Dial: Multiple Options Available

– Bezel: Fixed, 18k White Gold, Fluted-Style

– Crystal: Sapphire

– Movement: Rolex Caliber 3155

– Strap/Bracelet: Leather Strap

– Approx. Price (USD): $21,500 – $28,000 (Pre-Owned)

Gold Rolex watches are highly revered among enthusiasts, as they represent status symbols and offer rock-solid investment potential, particularly on the pre-owned level.  The Day-Date “President” is one of the most recognizable gold Rolex watches and has held the title of Rolex’s flagship watch collection ever since it was first introduced in 1956. While yellow gold is one of the most iconic editions of the Day-Date, conveying internationally recognized messages of success and achievement, it probably wouldn’t be your first choice as a casual timepiece.

That’s where the Rolex Day-Date 118139 comes into play. Crafted from 18-carat white gold, this reference is quite a bit less flashy while still exuding the same elegance that many Rolex Day-Date enthusiasts desire. It also opts for a supple leather bracelet instead of the traditional three-link President Bracelet option, making it both a little more under-the-radar and a bit easier to wear as you go about your day.

As a modern Rolex watch, the ref. 118139 also includes such amenities as a scratch-resistant sapphire crystal over the dial and an Oyster case that is water-resistant to 100 meters. You can strap this watch on and head out the door without worry. It also includes a cal. 3155 movement that operates on self-winding technology and consists of a very convenient Double Quickset function – a feature that allows the wearer to correct either the date or day mechanism on the dial without disrupting the time-telling hands.

Omega Speedmaster Reduced

Best Casual Watches for Men Guide OMEGA Speedmaster Reduced

Speedmaster Reduced Key Features:

– Case Size: 39mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds, 12-Hour Chronograph

– Dial: Black w/ Luminous Hour Markers

– Bezel: Fixed, Black Aluminum Insert w/ Tachymeter Scale

– Crystal: Hesalite

– Movement: Omega Caliber 3220

– Strap/Bracelet: Stainless Steel Bracelet or Leather Strap

– Approx. Price (USD): $3,200 – $4,500 (Pre-Owned)

The Omega Speedmaster was the first watch on the Moon. It is the object of many collectors’ desires and it is available in various different feature sets. The classic Omega Speedmaster Professional Moonwatch features a 42mm case. Other options in the series also include the Speedmaster Racing edition measuring 44.25mm in diameter and the Speedmaster ’57, which measures 41.5mm. With that in mind, at 39mm, the Speedmaster Reduced is noticeably smaller. It’s incredibly comfortable to wear while also taking a somewhat modest stance on the wrist.

The Omega Speedmaster Reduced also features the durability and highly functional chronograph movement that made the Speedmaster NASA’s top choice for space exploration. From the silky, multi-link bracelet to the slim tachymeter bezel and iconic chronograph registers on the dial, the Omega Speedmaster is a horological masterpiece. Versions, such as the ref. 175.0032.1 with a Hesalite crystal and self-winding movement, are available on the secondary market in excellent condition.

Panerai Luminor PAM423

Best Casual Watches for Men Panerai Luminor PAM423

Lumino Pam423 Key Features:

– Case Size: 47mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds, Power Reserve Indicator

– Dial: Black w/ Luminous Hour Markers

– Bezel: Fixed, Stainless Steel, Smooth Style

– Crystal: Sapphire

– Movement: Panerai Caliber P.3002/1

– Strap/Bracelet: Rubber Strap

– Approx. Price (USD): $8,500 – $10,000 (Pre-Owned)

Panerai has been producing watches for decades. However, they didn’t enter the commercial market until the 1990s. Before Hollywood actor Sylvester Stallone brought massive attention to the brand in the 1996 thriller Daylight, Panerai was solely a military timepiece. With roots as a dive watch for the Italian Navy, Panerai has since enjoyed massive success with a varied collection of reliable waterproof wristwatches that are often distinguished by their robust, cushion-shaped cases and legible baton and Arabic markers on the dial.

The Luminor PAM 423 also includes Panerai’s signature crescent crown guard bridge. The mechanism was developed to ensure that the crown remains secure while on the wrist, therefore guaranteeing the watch’s water resistance. It’s also a key part of the Luminor’s signature design that has since garnered the watch immense adoration among Paneristis.

This Panerai PAM 423 is the largest timepiece in our guide at 47mm in diameter; however, it is another casual watch that you can sport without worrying about everyday wear and use. It features a Cal. P.3002/1 hand-wound movement with a 3-day power reserve and a handy power reserve indicator. Vintage-inspired yet equipped with a bevy of modern amenities, the Panerai PAM 423 is the best of both worlds.

Rolex Oyster Perpetual 114300

Best Casual Watches for Men Rolex Oyster Perpetual 114300

Oyster Perpetual 39 Key Features:

– Case Size: 39mm

– Materials: Stainless Steel

– Functions: Time/ Running Seconds

– Dial: Multiple Options Available

– Bezel: Fixed, Stainless Steel, Smooth Style

– Crystal: Sapphire

– Movement: Rolex Caliber 3132

– Strap/Bracelet: Oyster Bracelet

– Approx. Price (USD): $8,500 – $11,500 (Pre-Owned)

The Rolex Oyster Perpetual is one of the company’s longest-produced models. At its core, beats a Perpetual movement with Rolex’s self-winding technology. It also includes Rolex’s patented Oyster case, which boasts water-resistance up to 100 meters on modern references. You can wear the Oyster Perpetual almost anywhere without damaging the movement within, making the collection perfect for everyday casual wear.

With a time-only dial, smooth bezel, and all-around sophisticated styling, the ref. 114300 in stainless steel has all the makings of the perfect casual watch. It’s available with multiple dial color options, from classic white or black to more striking red grape, and it includes a 39mm case, the largest option currently available within the Oyster Perpetual collection. Deemed the “Quintessential Oyster” by Rolex, it doesn’t get any better than the ref. 114300.

Tudor Black Bay

Best Casual Watches for Men tudor black bay blue 79220B

Black Bay Key Features:

– Case Size: 41mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds

– Dial: Black w/ Luminous Hour Markers

– Bezel: Unidirectional, Blue Aluminum Insert w/ 60-Minute Scale

– Crystal: Sapphire

– Movement: Tudor Caliber MT5602

– Strap/Bracelet: Stainless Steel Bracelet, Leather Strap, or Canvas Strap

– Approx. Price (USD): $3,000 – $3,800 (Pre-Owned)

At first glance, the Tudor Heritage Black Bay resembles the iconic Rolex Submariner. The Tudor brand was actually founded by Rolex founder, Hans Wilsdorf. His goal was to offer the same quality as a Rolex timepiece, but at a much more affordable price point. If you love the Submariner’s versatility but not its sky-high price tag, then the Tudor Black Bay is a great option to consider.

The ref. 79220B takes numerous design cues from the Submariner with contrasting 60-minute graduations on the bezel, a bold luminous display on the dial, and a reliable self-winding movement. It doesn’t feature the same depth rating, with the Submariner offering resistance up to 300 meters and the Black Bay offering users 200 meters. However, it’s still an impressive timepiece that is easy to wear, incredibly reliable, and perfectly suited for everyday use.

Oris Artelier

Best Men' Casual Watches Oris Arterlier Small Seconds

Artelier Key Features:

– Case Size: 42mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds, Date Display

– Dial: Silver w/ Guilloche Pattern

– Bezel: Fixed, Stainless Steel, Smooth Style

– Crystal: Sapphire

– Movement: Oris Caliber 744

– Strap/Bracelet: Leather Strap

– Approx. Price (USD): $1,100 – $1,300 (Pre-Owned)

For around $1,000, you can add the Oria Artelier Small Second Pointer Date to your watch rotation. It offers the class of a traditional dress watch while maintaining a level of wearability with a leather bracelet and a stainless steel finish. It features a sapphire crystal with anti-reflective treatment and is water-resistant up to 5 bar. It also includes a self-winding 28-jewel movement with small seconds at the 9-hour marker and an innovative pointer date mechanism. Overall, the Oris Artelier is an ideal everyday watch with sleek, timeless styling and an elegant yet durable case.

Rolex GMT-Master II 116710LN

Best Casual Watches for Men Rolex GMT-Master II 116710 ceramic bezel

GMT-Master II 116710LN Key Features:

– Case Size: 40mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds, Date Display, GMT-Functionality

– Dial: Black w/ Luminous Hour Markers

– Bezel: Bidirectional, Black Ceramic Insert w/ 24-Hour Scale

– Crystal: Sapphire

– Movement: Rolex Caliber 3186

– Strap/Bracelet: Oyster Bracelet

– Approx. Price (USD): $14,000 – $18,000 (Pre-Owned)

Developed specifically for airline pilots and travel, the Rolex GMT-Master II is now one of the most sought-after tool watches in the Rolex lineup. It’s highly functional with a 24-hour bi-directional bezel and a dedicated GMT hand on the dial, which can be used to reference multiple time zones. If you’re in the market for a casual timepiece that’s also perfect for travel or business, you can’t go wrong with the Rolex GMT-Master II.

While the collection includes several metal options and bezel colors, the ref. 116710 with a black dial, all-black ceramic bezel, and an Oystersteel case and bracelet is perfect for everyday wear. It isn’t too flashy and also offers the durability of highly resilient 904L-grade Oystersteel. The reference 116710 also includes an upgrade from the Twinlock screw-down crown to the Triplock crown for even better water-resistance than its 5-digit predecessors. The bezel is outfitted with a ceramic insert, which is celebrated for being highly resistant to scratches, fading, and corrosion. Pair these upgrades with a scratch-resistant sapphire crystal, and you’ve got one seriously tough watch that is easy to wear as you go about your day.

Rolex Explorer II 16570

Best Casual Watches for Men Rolex Explorer II 16570 Black Dial

Explorer II 16570 Key Features:

– Case Size: 40mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds, Date Display, GMT-Functionality

– Dial: Black or White w/ Luminous Hour Markers

– Bezel: Fixed, Stainless Steel w/ 24-Hour Scale

– Crystal: Sapphire

– Movement: Rolex Caliber 3185 or Caliber 3186

– Strap/Bracelet: Oyster Bracelet or Jubilee Bracelet

– Approx. Price (USD): $9,000 – $12,500 (Pre-Owned)

Only offered in stainless steel, the Rolex Explorer II is, by many enthusiasts’ standards, a casual luxury watch. Its design is straightforward with a bright, luminous display on the dial, a fixed 24-hour bezel, and a standard 40mm case and three-link bracelet. It’s easy to wear while also offering the functionality of a traditional Rolex tool watch. The Explorer II also boasts Rolex’s celebrated Perpetual movement with self-winding technology and a screw-down crown with a 100-meter depth rating. It will read true whether you’re at the office, climbing Mount Everest, or playing golf.

The ref. 16570 Explorer II’s production spans several decades, beginning around the late 1980s and continuing into the 2000s. There are various editions available on the pre-owned market that vary in luminous material and movement used. It’s a Rolex watch that is still obtainable by many budgets, which is also fun to hunt for on the secondary market. The black dial ref. 16570 Rolex is a cult favorite among collectors for its timeless feature set. It captures the attention of everyone you shake hands with while keeping things understated and classy.

Rolex Submariner 16610

The Best Casual Watches for Men Guide Rolex Submariner 16610 Black

Submariner 16610 Key Features:

– Case Size: 40mm

– Materials: Stainless Steel

– Functions: Time w/ Running Seconds, Date Display

– Dial: Black w/ Luminous Hour Markers

– Bezel: Unidirectional, Black Aluminum Insert w/ 60-Minute Scale

– Crystal: Sapphire

– Movement: Rolex Caliber 3135

– Strap/Bracelet: Oyster Bracelet

– Approx. Price (USD): $10,500 – $14,000 (Pre-Owned)

Even if you’re not familiar with the Rolex brand, chances are, you know the Submariner. It’s a prominent fixture in pop culture and film, with its most notable appearances including the James Bond movies Dr. No and License to Kill. While the collection includes numerous metal options and dial/bezel colors, the most sought-after remains the classic stainless steel and black dial and bezel variation. It is the epitome of effortless casual tool-watch design with a tough exterior, a reliable movement, and modern styling that won’t weigh down the wrist.

The ref. 16610 is one of the most recognizable editions of the steel Rolex Submariner available today. It includes many of the amenities that the modern collector seeks, such as a scratch-resistant sapphire crystal, a reliable cal. 3135 self-winding movement with a date mechanism, water-resistance up to 1,000 feet, and a striking luminous display. This watch is easy to wear and transitions from day to night or from the boardroom to the beach without skipping a beat. When it comes to casual watches, the Rolex Submariner 16610 is a popular choice.

Oris Divers Sixty-Five

Best Casual Watches for Men Oris Divers Sixty-Five 65 42mm

Divers Sixty-Five Key Features:

– Case Size: 36mm, 38mm, 40mm, or 42mm

– Materials: Stainless Steel, Bronze, or Stainless Steel & Bronze

– Functions: Time w/ Running Seconds, Date Display

– Dial: Multiple Options Available

– Bezel: Unidirectional, Aluminum or Bronze Insert w/ 60-Minute Scale

– Crystal: Sapphire

– Movement: Oris Caliber 733

– Strap/Bracelet: Metal Bracelet, Leather Strap, Rubber Strap, or Nylon Strap

– Approx. Price (USD): $1,000 – $2,500 (Pre-Owned)

The Oris Divers Sixty-Five is another classic dive watch worthy of our list with an affordable price point, precision movement, and durable feature set. It puts retro design front and center with a domed crystal, vintage-inspired font, and luminous material in a warmer hue meant to resemble the natural patina on an older watch. As a modern timepiece, it also includes a crystal constructed from scratch-resistant sapphire and bright Super-LumiNova lume.

The Oris Divers 65 is the perfect daily watch that we think looks phenomenal with jeans or business attire. And with its price tag, the collection is hard to resist for anyone who seeks a timeless watch that they can wear virtually anywhere.

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Paul Altieri