Style Guide: Rolex Datejust Featuring Buck Mason Garments

There’s a saying we have about the Rolex Datejust here at Craft + Tailored: It could just as easily be your first Rolex as it could be your last. The Datejust has a nearly unbeatable combination of deeply respected heritage, aesthetic versatility, and unfettered functionality that makes it the ultimate candidate for what we call a one-watch-collection – or a piece that truly does it all. From the beach to black tie, the Datejust simply works with everything and it does so without feeling forced. There’s no overstating what an icon the Datejust is; not only is it the piece most of us see in our mind’s eye when we hear the word “Rolex,” but it’s a watch design that’s transcended the horology space altogether. Furthermore, the Datejust’s design was arguably perfected in its infancy, and like other design icons – like the Fender Stratocaster or the Porsche 911 – it’s been produced in essentially the same immediately recognizable form factor since its debut in the late ‘50s. Of course that design has been honed, evolved, and materials and finishing techniques have been experimented with over the years, but the Datejust has remained fundamentally the same since its inception. With a production run like that, there’s a lot of variance and unique choices to be found within the world of vintage Datejusts, which means taking advantage of this iconic model’s versatility and relatively carefree ownership doesn’t come at the cost of personality or enjoying a unique example of the model.

Being that the Datejust is what myself and most dealers consider the perfect place to start in the vintage watch world, we wanted to put our money where our mouth is and really drive home its unbeatable versatility by pairing a classic Datejust ref. 1601 in steel with both a casual daytime look and a more elevated evening look. With the help of NYC-based stylist Turner Allen and pulling from the current line up of modern classic menswear brand Buck Mason – a company whose clothing I already love and wear in my day-to-day – we did just that.

For over 70 years, the Rolex Datejust has stood the test of time as possibly the most beloved choice amongst both watch enthusiasts and those simply looking for an elevated, timeless, but daily-wearable wristwatch. The Datejust’s enduring appeal lies in its classic design and technical excellence, which embody elegance, practicality, and the very spirit of Rolex sports watches. The Datejust is considered by many to be the most versatile wristwatch ever made, and it’s a design that effortlessly transitions between different levels of formality with ease. Despite various iterations and vamps on the form factor over the years, the core design of the Datejust has remained constant: A refined and understated timepiece that effectively and legibly displays the time and date. In essence, the Rolex Datejust represents the perfect marriage of form and function.

To pay homage to the watch’s considerable heritage, I aimed to craft sophisticated, yet functional ensembles using light layers, understated fabrics, and neutral shades. The aim was to create outfits that conveyed ease while maintaining a sense of sophistication. For the daytime outfit, I took inspiration from workwear and how its practical roots complemented the Datejust’s upscale, yet utilitarian design. As the emphasis wasn’t on bold colors here, I relied on contrast to make the outfit pop. The Buck Mason Field Olive Craftsman Jacket was my initial choice. Constructed from stretch canvas, this jacket resembles a chore jacket but boasts refined elements like a sueded finish and corduroy collar, adding visual and tactile texture. To balance the color palette, I paired the jacket with sturdy Buck Mason Officer Pants in black and a simple cream-colored Pima Curved Hem Henley. We finished off the look with some distressed sneakers, resulting in a smart casual daytime outfit that could effortlessly take Cam from early morning Zoom calls to a client lunch without any fuss.

Since the daytime attire was more laid-back, I aimed to concoct a sophisticated, yet unassuming evening outfit that would be suitable for happy hour or a relaxed dinner. Inspired by the Datejust’s iconic stature, I aimed to create an equally iconic and universally appealing look. This entailed opting for a classic combination of blue jeans, a polo shirt, and a navy blazer. Though this may appear mundane at first glance, by carefully incorporating a variety of textures, we achieved a timeless look that was anything but boring. I paired Buck Mason’s vintage-inspired mid-wash Ford Standard jeans with their plush Sueded Cotton Polo to ground the look in familiarity, but with a bit of high end finishing. To top it off, I added a professorial-style, soft-tailored corduroy blazer (High-Ridge Cord Carry-On Jacket) and a chic leather ankle boot for a touch of edginess. My goal was to honor the watch’s incredible legacy and mirror its versatility by designing an outfit that seamlessly shifts between various degrees of formality, all while exuding refinement and practicality.

Promotional consideration provided by Buckmason. Photos by Rio Asch Phoenix follow him on IG @rioaschphoenix, right?