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

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It’s been a while since the last installment of our popular Three-Watch Collection Under $5,000 series. We’ve already seen picks from Ilya, Mark, Hung, Sean, Christoph, Brad, ZQZach, and Jon. Today, Ed Jelley—Worn & Wound’s newest contributor—breaks down his three choices.

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.


The hypothetical three-watch collection under $5,000 is a fun thought experiment. It’s enough money for some great pieces, but balancing the budget between three watches can definitely be a challenge. Here’s some quick details about my typical day to help put my choices into perspective. 

A day in the life of Ed Jelley isn’t super crazy. I’m 30-years-old, a father to a toddler, and work in an office environment that’s relatively close to home. My daily “uniform” is almost always a button down Oxford shirt, dark raw/black jeans, and a pair of desert boots. No intense work environment, no crazy commute, and I don’t have to dress up all that much. My ideal three watch collection includes a piece that can be dressed up or down for work, a chronograph, and a beater/vacation watch that’ll stand up to the occasional swim/hike/adventure. Let’s start with the…

Tudor Black Bay 36 Blue – $2,850

There might be a little bit of honeymoon phase bias at play here, but I’m enjoying my new Tudor Black Bay 36 Blue so much that I will happily devote a large chunk of my budget to this watch. My colleagues have deemed the BB36 as a “Dressy Tool Watch” or DTW for short, and I can’t agree more. The solid construction, impressive water resistance, diver-esque dial, and proportions that remind me of the classic Rolex Explorer I make the BB36 an excellent everyday watch.The mix of polished and brushed surfaces are equal parts casual and dressy, making the watch easy to dress up or down. It’s at home with nearly any outfit thanks to the versatile shade of blue Tudor chose for the dial.

I also think I’m in love with the 36-millimeter case and 10.25-millimeter height. The smaller size of the watch makes it very comfortable to wear — staying out of the way when you bend your wrist and effortlessly slipping under a cuff. Small details like the applied indices and finishing on the case (radial brushing on the lugs, high polish on the slab sides, and subtle chamfer in between) really make the watch a great value. To me, this watch feels like the perfect allrounder whether I’m plugging away at my desk or out and about on the weekend.

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Sinn 356 Flieger Acrylic on Strap – $1,870

In my three-watch collection, I would love a chronograph. I use my Speedmaster for timing everything from the laundry to the length of my morning espresso shot (usually shoot for 18.5g coffee in, 40g out in 25-30 seconds in case you were wondering). In addition to the chronograph functionality, I love the way they look. Since the Speedy is priced out of bounds for this challenge, I’d swap in the Sinn 356 Flieger with acrylic crystal. This watch checks off two boxes for me at the same time — a flieger-style watch and a chronograph. I prefer the vintage vibe and warmth that the acrylic crystal provides, and it saves a few bucks over the sapphire version. The 356 also has a day-date display for added functionality. Another reason for this choice is that it’s at home on a variety of straps. I like to switch up straps depending on my mood and outfit, and the BB36 with its blue dial isn’t nearly as versatile as the stark brushed steel/black/white color scheme of the 356. The 356 looks handsome on leather, right at home on a rally-style strap, and tough on a nylon mil-strap.

Seiko SKX173 – $249

It’s hard to think of any collection, let alone one with a price constraint, that doesn’t have a Seiko SKX in it. This classic, reliable diver is a great affordable option that’s built like a tank. Instead of the more-popular SKX007 model, I would snag the 173. It’s the same watch, save for a slight tweak in the dial design. One the 173 variant, you’ll find rectangular indices in place of the circles and rounded rectangles on the 007. Everywhere else, you’ll find the same specs. A 200-meter water-resistant case, unidirectional dive bezel, and reliable automatic movement with day/date display round out a solid set of features.

Like the 356 mentioned above, the SKX173 plays nice with a variety of different straps thanks to the basic color scheme. At 42 millimeters, it would be the largest watch out of my three picks, but the relatively short lug-to-lug distance and thicker bezel make the SKX wear a bit smaller than its size implies. I can appreciate a watch that doesn’t cost a fortune that you’re not afraid to wear. My SKX is always on my wrist for house and yard work, swimming in the summer, and pretty much any time when I want to wear a mechanical watch that can take a beating. It’s hard to imagine my hypothetical three-watch collection without it.

There you have it! My three watches under $5,000. If all valued at MSRP, I have a whopping $31 left over which I would probably spend on a strap or two to keep things interesting.

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Ed is a Long Island-based writer and photographer with an affinity for watches, fountain pens, EDC gear, and a great cup of coffee. He’s always looking for the best gear for the job—whether it be new watch, pen, flashlight, knife, or wallet. Ed enjoys writing because it’s an awesome (and fulfilling) way to interact with those who share the same interests.
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