The Omega Speedmaster is a watch that unifies all collectors. It’s arguably the most iconic chronograph ever made and pairs a strong, utility-focused visual and functionality with a rich history that no other chronograph can really compare with. Not only is the Speedy the only timepiece NASA has ever officially issued astronauts, but it’s been a favorite of famous racing drivers, aviators, and more. It’s a true tool watch that’s proven its worth and abilities time and again in some of the most demanding fields of all time, which makes it more than just a luxury item, but a way to align yourself with the people that relied on these watches as a part of their kit to get remarkable things done. Unlike any other famous chronograph with a similar heritage, the Omega Speedmaster – both modern and vintage examples – has remained relatively approachable from a price point, making it a favorite entry point into the world of fine wristwatches. In this style guide, Craft + Tailored’s CEO Cameron Barr and men’s style expert and NYC-based personal stylist Turner Allen pair the iconic and unexpectedly versatile Omega Speedmaster with pieces from menswear titan Buck Mason to underline just how flexible the Speedy truly is, but especially so in the context of Buck Mason’s classic, rugged, yet upscale garments.
When I meet clients that are completely fresh to the world of elevated watches, I often find the Omega Speedmaster is the perfect piece to start. It’s an icon that’s beloved by almost all collectors, has an untouchable pedigree in space exploration as the only watch NASA ever officially issued its astronauts, and it’s a relatively affordable option, regardless of whether you’d prefer a vintage example or newer one as they’ve been produced in essentially the same fundamental form since the late ‘50s. Despite its utility-first aesthetic, the Speedy is a surprisingly versatile watch to own; in fact, I have a 1985 example in my personal collection that I wear on a weekly basis.
A tool watch like the Speedmaster as a primary high end timepiece (or your only wrist watch period) is a great option for men that tend to spend most of their week dressed casually. However these watches can offer an unexpectedly upscale look – especially when paired with a handmade leather strap. It’s something I think they don’t get quite enough credit for in the watch community, but as we’ve seen with other high end tool watches like the Rolex Submariner and Daytona, these watches look just as at home with a tux in 2023 as they do with shorts and a tee shirt. The great thing about the Speedmaster is that because they’ve been produced in essentially the same form for so long, you have a lot of options when it comes to price point, collectability, and provenance – which means you can get a similar overall feel and wrist presence from a highly sought after “pre-moon” example from the late ‘60s as you do from the standard Speedmaster Professional “Moonwatch” you can walk out of the Omega boutique with today. That said, there’s simply no substitute for the look and spirit of a true vintage watch and a ‘60s Speedmaster is always going to be one of the most respectable daily-wearable vintage timepieces you can get your hands on. It’s a watch I’ll always feel confident recommending to nascent collectors.
The Omega Speedmaster is one of the most recognizable and versatile luxury watches in the world, making it a popular choice for newcomers to the luxury watch game. Its design and functionality were born out of necessity and invention, as it was created to be easily visible to the naked eye at night for pilots. Despite being designed with a specific need in mind, the Omega Speedmaster’s versatility allows it to be worn in both formal and casual settings. While the watch’s history is rich and intriguing, its wearability is what makes it an attractive choice for many, even if wearers don’t have any plans to fly a plane. With the help of Buck Mason and Cam’s existing wardrobe, assembling stylish outfits for both daytime and nighttime is a breeze.
The Speedmaster’s design is rooted in practicality, and I wanted to incorporate this functionality into each outfit. To achieve this, I chose Buck Mason’s incredible Ridge Upland Jacket in dark navy as the anchor piece for our daytime look. Selecting one key item of clothing to base the outfit around is the best place to begin rather than trying to put everything together at once. Since many of my personal styling clients struggle with decision fatigue when it comes to getting dressed, I recommend focusing on one dominant piece of clothing and selecting accompaniments that will enhance it instead of competing for attention. This approach can alleviate the stress of decision-making and result in a more cohesive and polished outfit. I selected Buck Mason’s pima curved hem henley in color “natural” to showcase the Upland Jacket’s rich hue and thoughtful details. To further emphasize the jacket’s prominence, I paired it with a fresh pair of white jeans, an often-overlooked item in men’s wardrobes. To balance the overall look, we added a basic black leather belt and a pair of Cam’s trusty black leather boots.
Rather than a dull and unremarkable outfit that blends in, I crafted a straightforward yet impactful look that exudes a sense of freshness and ruggedness. This versatile ensemble can be worn in a variety of settings, making it an excellent choice for many occasions.
For the night time outfit, I aimed to maintain the relaxed vibe of the daytime look but with a nod to the Speedmaster’s icon status. I wanted to channel the “King of Cool” Steve McQueen, but in a way that reflected Cam’s personal style. As with the daytime ensemble, I started by selecting a central piece to base the outfit around: Buck Mason’s Bruiser Bomber jacket in buttery black leather. To complement the jacket’s timeless appeal, I paired it with my client’s favorite Buck Mason Pima curved hem t-shirt in classic white. To further emphasize the timeless nature of this look, I chose classic blue jeans, black penny loafers, and a simple chain necklace for a touch of visual interest. Although loafers may seem like an odd pairing with a bomber jacket and t-shirt, the mix of casual and formal elements creates a well-balanced look that doesn’t feel too expected. While each piece is straightforward on its own, the combination results in a cohesive ensemble that will stand the test of time. How’s that for versatility?
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