Three-Watch Collection Under $5,000: Sean’s Picks

We’re back with the fourth installment of our popular Three-Watch Collection Under $5,000 series. We’ve already seen Ilya’s, Mark’s, and Hung’s picks. Today, Sean–one of worn&wound’s longstanding writers and hardcore automotive enthusiast–breaks down his three.

A quick refresher on the parameters before we get started. We chose $5,000 as the cap for the simple reason that $5,000 is generally regarded as a point of entry into luxury. So rather than drop all that coin on a single watch, we thought it’d be interesting to see how our team plays around with that number. Furthermore, the choices aren’t limited to specific categories of watches. Our contributors can choose watches they’d like based on their needs and personal preferences. Finally, for the sake of consistency, all watches currently being produced have to be valued at their MSRP. Vintage or recently retired models should be based on the average market rate.

Without further ado, let’s get to it.


This was an easy one. I’m a huge chronograph geek, and if you’ve ever seen my Watches and Formula 1 series you’ll know I’m an even bigger racing geek. The Speedmaster Schumacher sits right at the crossroads of these two great passions for me. The Omega Speedmaster Automatic, in my opinion, is a serially overlooked option in the chronograph segment. While it may not have the cachet of the Moonwatch, the reduced 39mm size makes it an easy choice for daily wear.

Omega Speedmaster Schumacher Automatic Ref. 3510.61 - Rakuten
Image source: Rakuten, seller “chuukotokei”

This particular Speedmaster, made to commemorate Formula 1 legend Michael Schumacher’s move to Scuderia Ferrari in 1996, captures an important part of racing history as well. Schumacher would go on to win five World Driver’s Championship titles in his ten-year stint at Ferrari, bringing his grand total to a record seven titles and a record 91 grand prix victories–by almost any measurement, making him the greatest of all time. The unmistakable red dial and classic Speedmaster case make it a solid addition, particularly at an average price of $2,000.

Omega Speedmaster Schumacher Automatic Ref. 3510.61 - Rakuten 2
Image source: Rakuten, seller “chuukotokei”


Every collection needs a diver, right? You’ll probably see this one appear on a few of our writers’ lists, and that’s no coincidence. For the money, this might be my favorite watch on sale today. At the very least, it’s in the top three. I was lucky enough to have the 40 millimeter version in for review a few years ago, and in the short time it spent in my care I fell head over heels for it. Everything about it– the case, the proportions, the finish–was absolutely spot-on perfect for a modern reinterpretation of a vintage diver, and the 42mm version classes the original design up with more traditional markers without losing any charm.  01 747 7715 7754-Set - Oris Force Recon GMT Edition INot to mention the stunning, deep-blue dial, low profile contrasting bezel, and the optional rivet bracelet. While it may only have a lightly modified SW200 under the hood, the Oris Divers Sixty-Five 42mm is a good value at the starting price of $1,900. That said, I’d stretch for the bracelet version for $2,300. Honestly, how often do you come across a good rivet oyster these days?


Rounding out the three is a dressy choice with a ton of personality. The Seiko “Cocktail Time” is remarkably versatile, fitting everywhere from casual to full dress, but carrying a different vibe than most dress offerings. Supposedly designed with assistance from one of Japan’s most famous mixologists, the Cocktail Time’s radiant sunburst dial displays a range of colors from silver to a light icy blue depending on light, calling to mind high-end crystal tumblers. The multifaceted indices add some additional sparkle while remaining refined.

Image source: twoplustwo forum, user Gaddy

While the 6R15 movement on display isn’t the most attractive piece of hardware, it’s a reliable in-house power plant with hacking that has proven itself time and again in Seiko’s current line. Overall, it’s a natural choice, and now that it’s being replaced with a newer iteration under the Presage line, the SARB065 is a steal at the street price of  roughly $450.

A watch collection is as much an outlet for personal expression as it is anything else, and these three pieces cover all the bases for general needs while at the same time reflecting my own personal style. $5,000 can go a long way with a little work, and these three certainly represent money well spent.

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Hailing from Redondo Beach, California, Sean’s passion for design and all things mechanical started at birth. Having grown up at race tracks, hot rod shops and car shows, he brings old-school motoring style and a lifestyle bent to his mostly vintage watch collection. He is also the Feature Editor and Videographer for Speed Revolutions.