The Ultimate Guide to Iconic Rolex Dress Watches

As a follow up to our Iconic Rolex Sports Watches feature, we’re now delving into iconic Rolex dress watches. From ultra-luxurious Day-Date President watches to simple everyday Oyster Perpetual timepieces, the assortment of Rolex dress watches is extremely varied and suits a range of tastes and budgets.

Rolex Air-King

Rolex Air-King

While today’s 40mm Air-King is without a doubt a sports watch, older versions of the Air-King were not. In fact, prior to the most recent iteration, Rolex Air-King watches were classic dress timepieces with restrained 34mm Oyster cases and simple dials.

The Air-King made its debut in 1945 to honor British fighter pilots that served during World War II. The majority of Air-King models throughout the watch’s long history have been straightforward three-hander models without a date window, but there are a few Air-King Date watches too. Although the current Air-King is only available in stainless steel, the Air-King lineup was actually a varied collection with models in steel, two-tone steel and gold, and even yellow gold shell.

Rolex Oyster Perpetual

Rolex Oyster Perpetual

With a history that dates back to the 1930s, the Rolex Oyster Perpetual is one of the brand’s longest running collections. And because of its longevity, there’s an abundance of styles to choose from for both men and women. Though the Oyster Perpetual is a time-only Rolex, there are a handful of sizes ranging from 39mm down to 24mm and material choices include steel, two-tone yellow gold and steel, as well as gold shell. However, similar to the Air-King, the brand only offers current Oyster Perpetual watches in stainless steel and has positioned this particular dress watch as an everyday entry-level Rolex.

The two main characteristics of the Rolex Oyster Perpetual watches are that they are waterproof thanks to the Oyster case and that they are automatic timepieces running on perpetual mechanical movements.

Rolex Oysterdate Precision

Rolex Oysterdate Precision

The Oysterdate Precision is somewhat of an anomaly in Rolex’s archives of dress watches. Manufactured from the 1950s until the 1980s, the Oysterdate is, in fact, a manual-wound watch. Furthermore, it is not COSC-certified, explaining the use of “Precision” on the dial rather than the ubiquitous “Superlative Chronometer Officially Certified” label.

As its name suggests, the Oysterdate offers the date function in addition to the central hour/minute/seconds hands. Barring a few older examples, the Oysterdate was almost exclusively made with a 34mm steel Oyster case and steel Oyster bracelet.

Rolex Oyster Perpetual Date

Rolex Oysterperpetual Date

Officially called the Rolex Oyster Perpetual Date but more commonly referred to as the Rolex Date, this dress watch marries elements of the Oyster Perpetual and the Oysterdate Precision. It is an automatic Rolex watch that includes a date window at 3 o’clock.

While contemporary Rolex Date watches are only available with a 34mm stainless steel case and Oyster bracelet, the model was previously made available in steel, two-tone steel and gold, or full yellow gold. Plus, sizes ranged from 34mm for men, 31mm as the midsize option, and 26mm for women. There was even a choice of a Jubilee bracelet too.

Rolex Datejust, Datejust II, & Datejust 41

Without a doubt, the Datejust is Rolex’s signature dress watch collection. Immediately recognizable and highly coveted, the Datejust is one of Rolex’s most diverse in terms of sizes, materials, and styles.

Introduced in 1945, the inaugural Datejust made waves in the industry as the first automatic wristwatch to indicate the date via an aperture on the dial. It was also the watch that introduced the now-famous five-link Jubilee bracelet to the world.

Rolex Datejust 41

Available in steel, two-tone steel and gold, and solid gold, the Datejust sports a 36mm Oyster case. Wearers can choose from the iconic fluted bezel, sporty engine-turned bezel, the modern smooth finish domed bezel, or a precious diamond-set bezel. And joining the original Jubilee bracelet are Datejust models with sportier Oyster bracelets. Dial designs are abundant with a range of hour markers styles, colors, and patterns to choose from. But the signature date window is always present, magnified by the just-as-famous Cyclops lens on the crystal above it.

In 2009, Rolex announced a larger version of the sought-after dress watch with the Datejust II. This time, the men’s Datejust came with a bigger 41mm case, bulkier lugs, and a more robust look. Although only available with an Oyster bracelet, Rolex still ensured that the Datejust II line was a varied one with dial and material options. The bigger Datejust II is a popular choice for those looking for a sportier Rolex dress watch.

Just last year, at Baselworld 2016, Rolex replaced the Datejust II with the new Datejust 41. Although it comes with a 41mm case just like its predecessor, the Datejust 41 includes a slimmer profile, thinner bezel, the option of a Jubilee bracelet, and a new movement with an increased 72 hours of power reserve. Despite it being a relative newcomer to the Rolex dress watch family, the Datejust 41 is already establishing itself as an iconic men’s luxury watch.

Rolex Lady-Datejust

Rolex Lady Datejust

The Lady-Datejust is Rolex’s best selling model, ever. While this may shock some, it shouldn’t. Given its classic elegance, abundant variety, prestige, and automatic movement (most women’s watches run on quartz movements) it’s no surprise that the Lady-Datejust is a top seller. As a women’s luxury dress watch, it really can’t be beat.

First presented in 1957, the Lady-Datejust originally had a 26mm case but the larger Lady-Datejust 28 replaced it in 2015. Plus, there’s also the even larger midsize Datejust 31 for women. As expected, the women’s Datejust dress watch collection has plenty of materials, styles, gems, and colors. There are also several bracelet options including the Oyster and the Jubilee, in addition to the lavish solid gold President bracelet.

Rolex Day-Date, Date-Date II, Day-Date 40

If the Datejust is the company’s signature dress watch, then the Day-Date is its most prestigious. In 1956, Rolex unveiled the Day-Date as the first wristwatch to indicate both the date as well as the day written in full on the dial. With the Day-Date, Rolex introduced the President bracelet with a curvy semi-circular three-link configuration. In fact, it is because of this popular bracelet style—and the fact that the Day-Date has always been the go-to watch for global leaders and captains of industry—that the Day-Date is more commonly referred to as the Rolex President.

Rolex Day-Date 40

Exclusively available in either yellow gold, white gold, rose gold, platinum, or the unique Tridor (combination of yellow, white and rose gold), the traditional Rolex Day-Date President dons a 36mm Oyster case. Although the President bracelet played a part in the watch’s iconic status, today, the Day-Date is also available with an Oyster bracelet or leather strap.

At Baselworld 2008, Rolex launched the Day-Date II with a robust 41mm case. In view of its solid gold or platinum construction, this is a hefty Rolex dress watch indeed! But, Rolex eventually discontinued the Day-Date II to make way for the new Day-Date 40 in 2015. With a slightly reduced 40mm case, slimmer bezel, and thinner lugs, the Day-Date 40 wears quite smaller than its predecessor. But perhaps more importantly, the Day-Date 40 President comes equipped with Rolex’s new generation movement with a better accuracy rating of -2/+2 a day and 72 hours of power reserve.

Rolex Day-Date Masterpiece

Rolex Day-Date Masterpiece

A somewhat mysterious Rolex model is the Masterpiece, which is in actuality a special edition of the Day-Date. The Rolex Masterpiece features the signature duo of windows on the dial to indicate the day of the week and the date the month. However, the dial is housed within a 39mm Oyster case. Furthermore, rather than the President bracelet, the Masterpiece is equipped with a rounded five-piece links bracelet—identical in design to the ladies’ Pearlmaster bracelet.

Similar to the Day-Date President, the Day-Date Masterpiece is exclusively fashioned from gold or platinum. A particularly popular version is the Tridor edition, combining three shades of gold. The Rolex Masterpiece is one of the brand’s most exclusive (and elusive) men’s dress watches and always shines bright with a diamond-set bezel.

Rolex Oysterquartz

Rolex Oysterquartz

A true relic of its time, the now-discontinued Oysterquartz was Rolex’s answer to the quartz craze during the 1970s and 1980s. There were two main versions of the Oysterquartz—the Oysterquartz Datejust and the Oysterquartz Day-Date.

In addition to the in-house Rolex quartz movements ticking within the Oysterquartz watches, these dress watches are also distinct due to their integrated bracelets and angular 36mm Oyster cases. Similar to their mechanical counterparts, the Oysterquartz Day-Date watches are fashioned exclusively in gold and include an integrated-style President bracelet. There are also some lavishly diamond adorned versions. On the other hand, the Oysterquartz Datejust is available in either full steel or two-tone gold and steel, with a choice of integrated-style Oyster or Jubilee bracelets.

Rolex Milgauss

Rolex Milgauss

The quirkiest Rolex dress watch of the bunch, the Milgauss is unique in so many ways. Born during the big science boom in the mid-1950s, the Milgauss was constructed to withstand high magnetic fields. In fact, the Milgauss name comes from the French word for 1,000 (mille) and the unit used to measure magnetism (gauss). The first generation of Milgauss watches included large-for-the-era 38mm cases equipped with an iron shield to protect the movement from negative effects of magnetism. Also, on the dial sat a very cool lightning bolt seconds hand, paying homage to the scientific community it served.

Rolex then replaced the lightning bolt hand with a red-tipped seconds hand in the 1960s and produced the Milgauss until the late 1980s, when the collection was eventually discontinued. Thankfully, Rolex revived the Milgauss in 2007 with a 40mm steel case and the return of the lightning bolt hand.

Rolex Pearlmaster

Rolex Pearlmaster

Introduced in 1992, the Rolex Pearlmaster is the brand’s line of jewelry watches. Named after the rounded five-piece links Pearlmaster bracelet it is presented on, the Pearlmaster watch is always crafted in 18k gold and always adorned with diamonds. As a result, the Pearlmaster collection houses the most precious Rolex dress watches for women. In addition to diamonds, some ultra-lavish Pearlmaster models are embellished with other gems too, such as fancy colored sapphires.

The Rolex Pearlmaster is actually a special edition of the Datejust, as illustrated by the DATEJUST label on the dial. As such, all Pearlmaster watches feature the characteristic date window at 3 o’clock along with the magnifying Cyclops lens affixed to the sapphire crystal. The model is available with a choice of a smaller 29mm case, a midsize 34mm case, or a larger 39mm case. The Pearlmaster 39 only joined the collection in 2015 and its launch debuted the new generation time and date Rolex Caliber 3235 automatic movement.

Rolex Sky-Dweller

Rolex Sky-dweller

Currently the brand’s youngest model, Rolex unveiled the Sky-Dweller in 2012. Positioned as an ultra-luxurious traveler’s watch, the Sky-Dweller comes complete with dual time zones, a month indicator, and a date window. Because of its innovative and complex Rolex Cal. 9001, the Sky-Dweller will automatically adjust the calendar functions accordingly during those months with 30 or 31 days. It only requires one manual adjustment a year in February—thus the Sky-Dweller is indeed a Rolex annual calendar watch.

The Sky-Dweller is also one of the larger Rolex dress watches with a 42mm Oyster case. The case of the Sky-Dweller is always topped with a wide fluted bezel. The bezel is not just there for aesthetic purposes, but its position actually determines the function of the crown. Up until just this year, the Sky-Dweller was exclusively available in yellow gold, white gold, or rose gold. However, at Baselworld 2017, a two-tone yellow gold and steel Sky-Dweller and a steel Sky-Dweller with a white gold bezel joined the lineup.

Rolex Cellini

Rolex Cellini

Unbeknownst to many, in addition to the famous Rolex Oyster watches there is also the Rolex Cellini watch collection. The Cellini line is Rolex’s take on classic dress watches and traditional watchmaking. Named after the Renaissance man Benvenuto Cellini, Cellini watches have been a part of the Rolex catalog since 1928. Throughout its long history, the Cellini has taken on many forms including the rectangular Cellini Prince and cushion-shaped Cellini Danaos.

In 2014, Rolex re-launched the Cellini line with elegant and slim 39mm round cases and sophisticated leather straps. And for the first time, automatic movements replaced the previous manual-wind calibers. The new generation Rolex Cellini dress watches are available with a range of functions. There’s the Cellini Time, the Cellini Date, the Cellini Dual Time, and since Baselworld 2017, the Cellini Moonphase.

As you can see, Rolex offers an incredible variety of dress watches. Ranging from minimal everyday steel timepieces to opulent gold and diamond numbers, there’s an iconic Rolex dress watch out there for almost any wrist.