A thoughtfully chosen timepiece is more than just a way to tell the time. A timepiece can accent— and elevate— any look, enhancing your aesthetic with a touch of timeless luxury. For the stylish gentleman who is searching for the perfect luxury watch to add to his wardrobe, we’ve put together a list of some of our favorite newly listed men’s luxury timepieces. Read on to see our list of 5 of our favorite men’s luxury watches which, as an added bonus, are all under $5,000 (proving that attractive luxury watches can have equally attractive price tags).


1. 41mm Chanel J12 Chronograph Watch

41mm Chanel J12 Chronograph

Pre-Owned, $3,900

This 41mm Chanel J12 Chronograph provides the classic look of the stylish J12 sports watch, with its unmistakable black and white dial and black ceramic bracelet. Yet, this particular model also offers a more bold look, thanks to its dramatic oversized 41mm case. This model also features a beautifully designed chronograph function. The sub-dials of this chronograph J12 model are perfectly integrated into the J12’s sleek and sophisticated dial design.


2. 43mm IWC Schaffhausen Stainless Steel Pilot Chronograph IW377704

43mm IWC Schaffhausen Stainless Steel Pilot Chronograph 1W377704

Pre-Owned, $4,950

IWC Schaffhausen’s Pilot’s Watch Chronograph is a masterfully designed pilot’s watch. The Pilot’s Watch Chronograph features excellent dial legibility, exceptional performance, a celebrated automatic movement, and an impressive power reserve. The watchmakers at IWC Schaffhausen also outfitted this men’s watch with optimal protection from the elements. The Pilot’s Watch features soft-iron inner case that protects against external magnetic fields and a stainless steel case that is water resistant to 6 bar. This Swiss made pilot’s watch is sleek, streamlined, and ready for any adventure.


3. 44mm Breitling SuperOcean Stainless Steel Heritage Chronometer A2337024/BB81

44mm Breitling SuperOcean Stainless Steel Heritage Chronometer A2337024/BB81

Unworn, $4,850

This SuperOcean dive watch, by Geneva’s Breitling, is as stylish as it is functional. The SuperOcean was originally created in 1957 for professional and military divers and, as such, it provides superior performance as a diving watch. This particular model of SuperOcean is also a certified chronometer model that has met the exacting standards for precision set by the Controle Officiel Suisse des Chronometres (COSC). With a black bezel, black dial, and a stainless steel case and bracelet, this Swiss luxury watch model is also strikingly fashionable. The combination of high style and functional craftsmanship present in this men’s watch model makes it one of the most versatile watches on our list.


4. 34mm Rolex Stainless Steel Air-King 14000

34mm Rolex Stainless Steel Air-King 14000

Pre-Owned, $3,650


The Rolex Air-King is a favorite among Rolex collectors. The Air-King debuted in the midst of World War II and was created to honor the RAF pilots of the Battle of Britain. While the Air-King has excellent functionality, it’s most beloved by collectors for its distinctive look. This particular Air-King model is an Air-King 14000, a modern version of this classic pilot’s watch. This model features the classic Air-King look, yet has been updated with modern Rolex features, such as a sapphire crystal and the updated calibre 3000 automatic movement.


5. 36mm Rolex Datejust 16234

36mm Rolex Datejust 16234

Pre-Owned, $4,100


The Rolex Datejust is a legend in the world of watchmaking. The Datejust ranks high among Rolex’s most celebrated timepieces, alongside the Rolex Submariner, the Rolex President, the Rolex Yacht-Master, the Rolex GMT Master II, and the Rolex Cosmograph Daytona. The Datejust is famous for being the first wristwatch to ever have a date display and a quick date mechanism. Though date displays are common today, the Datejust has endured as a flagship Rolex model as its simple design and exceptional reliability are always in style.

This particular Rolex Datejust is a Datejust 16234 that features a number of unique design details that elevate the Datejust’s already stylish design. This model features a royal blue dial outfitted with roman numeral hour markers, a fluted bezel crafted from 18k white gold, and a sleek stainless steel jubilee band.

Final Thoughts

Haven’t found the ideal men’s watch for you?View our full collection of luxury timepieces . Our selection of the best luxury watches includes a vast array of watches from legendary watch brands such as Cartier, Patek Phillipe, Audemars Piguet (we do carry Royal Oak models), Tag Heuer, Jaeger-Lecoultre (we carry an excellent selection of Jaeger-Lecoultre dress watches), Panerai, and Omega (we carry numerous Omega Speedmaster models). We offer a variety of men’s watches in many styles, including watches that feature stainless steel, rose gold, white gold, yellow gold, diamond accents, leather straps, rubber straps, and stainless steel straps.