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100% Certified Authentic

Bob's Watches
100% Certified Authentic

At Bob's Watches, your trust is very important to us. We believe that buying a pre-owned Rolex watch online should be simple, honest, and straightforward. To that end, we guarantee that every Rolex watch on our site is 100% authentic, comprised entirely of Rolex parts. Our mission is to be the leading trusted online source for selling and buying authentic pre-owned Rolex watches. We stand behind this authenticity guarantee with a full money back refund on any watch not found to be completely genuine.

BOB’S WATCHES

ROLEX BLOG

Best Casual Watches for Men – Your Ultimate Style Guide

July 20, 2020

BY Paul Altieri

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If you’re in the market for men’s casual watches, this guide is worth a read. We’ve compiled some of the most versatile timepieces from the industry’s biggest names, such as Rolex, Omega, and Panerai, all at pre-owned prices that will meet nearly any budget. No matter where your day takes you, we’re confident that after browsing our casual watches collection on this list you will be able to find a luxury model that suits your lifestyle.

 

Rolex Air-King 5500 (Price: $3k)

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

Despite being a vintage reference, the Air-King 5500 is one of the most affordable Rolex watches available.

Key Features:

  • 34mm case in stainless steel
  • Time-only display
  • Screw-down crown and case-back
  • Acrylic crystal
  • Rolex Caliber 1520 or 1530 movement

Shop Rolex Air-King Watches


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 (Price: $16k)

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

A white gold Day-Date on a leather strap offers an understated take on this iconic Rolex classic.

Key Features:

  • 36mm case in 18k white gold
  • Time + day and date displays
  • Screw-down crown and case-back
  • Sapphire crystal
  • Rolex Caliber 3155 movement

Shop Rolex Day-Date 118139


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 (Price: $3.5k)

Best Casual Watches for Men Guide OMEGA Speedmaster Reduced

The Speedmaster Reduced offers much of the same appearance of the classic Moonwatch, just in a more compact size.

Key Features:

  • 39mm case in stainless steel
  • Chronograph complication
  • Tachymeter bezel
  • Luminous hands and hour markers
  • Omega Caliber 3220 movement

Shop OMEGA Speedmaster Watches


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 Speedmaste 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 ($6k – $7k)

Best Casual Watches for Men Panerai Luminor PAM423

The Luminor perfectly embodies the classic Panerai aesthetic.

Key Features:

  • 47mm case in stainless steel
  • Power reserve indicator
  • Locking crown protector bridge
  • Sapphire crystal
  • Panerai Caliber P.3002/1 movement

Shop Panerai Watches


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 (Price: $5k)

Best Casual Watches for Men Rolex Oyster Perpetual 114300

Crafted entirely from stainless steel, the Rolex Oyster Perpetual is perfect for everyday wear and use.

Key Features:

  • 39mm case in stainless steel
  • Time-only display
  • Screw-down crown and case-back
  • Sapphire crystal
  • Rolex Caliber 3132 movement

Shop Rolex Oyster Perpetual Watches


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 ($3k)

Best Casual Watches for Men tudor black bay blue 79220B

The Tudor Black Bay collection draws its design inspiration from vintage dive watches from the past.

Key Features:

  • 41mm case in stainless steel
  • 200 meters of water resistance
  • Screw-down crown and case-back
  • Sapphire crystal
  • Tudor Caliber MT5602 movement

Shop Tudor Black Bay


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 (Price: $1k)

Best Men' Casual Watches Oris Arterlier Small Seconds

Oris watches represent some of the best value for the money in the entire Swiss watch industry.

Key Features:

  • 42mm case in stainless steel
  • Pointer date display
  • Small running seconds indicator
  • Sapphire crystal
  • Oris Caliber 744 movement

Shop Oris Watches


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 116710 (Price $10k)

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

While it was designed for travel, the Rolex GMT-Master II also makes the perfect everyday watch.

Key Features:

  • 40mm case in stainless steel
  • Ceramic bezel insert
  • Additional 24-hour hand and GMT functionality
  • Sapphire crystal
  • Rolex Caliber 3186 movement

Shop Rolex 116710


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 referecne 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 (Price: $6k)

Best Casual Watches for Men Rolex Explorer II 16570 Black Dial

The Rolex Explorer II may have originally been designed for cave explorers, but it also makes a great watch for everyday casual wear.

Key Features:

  • 40mm case in stainless steel
  • Fixed 24-hour bezel
  • Additional 24-hour hand and GMT functionality
  • Sapphire crystal
  • Rolex Caliber 3185 movement

Shop Rolex 16570

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 (Price: $7k – $8k)

The Best Casual Watches for Men Guide Rolex Submariner 16610 Black

The Rolex Submariner 16610 is from the previous generation and it could easily be the only watch that you will ever need.

Key Features:

  • 40mm case in stainless steel
  • 300 meters of water resistance
  • Unidirectional timing bezel
  • Sapphire crystal
  • Rolex Caliber 3135 movement

Shop Rolex 16610


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 (Price: $1.2k)

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

The Oris Divers Sixty-Five collection offers vintage dive watch styling at an incredibly affordable price.


Shop Oris Divers Sixty-Five


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.

Key Features:

  • 42mm case in stainless steel
  • 100 meters of water resistance
  • Unidirectional timing bezel
  • Sapphire crystal
  • Oris Caliber 733 movement

WATCHES YOU MIGHT LIKE

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One Response to “Best Casual Watches for Men – Your Ultimate Style Guide”

  1. ioio says:

    Wow! Glad I popped by your blog. Thanks for sharing these great tips and ideas!

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