In this edition of our ongoing Three Watch Collection for $5,000 series, reader Elodie Townsend offers up a trio of watches that hit a variety of enthusiast touchstones. Elodie, a watch and automotive enthusiast based in California, has some fun with the format here, dividing up her choices into three distinct categories. Together, they form a cohesive, hypothetical collection with genuine variety and a ton of value. 

The idea of a three-watch collection totaling $5,000 is both enticing and daunting. As an automotive enthusiast, I’d wager that it mirrors the classic “three car garage” problem, but with even more potential for argument; the vastness of the used watch market and ever-changing design and style trends make any trio of timepieces ripe for debate. 

To either combat controversy or further court it, I’ve chosen three categories for my list: Busy, Affordable, and Conversation Starter. Basically, the “Busy” watch will embody the spirit of tool watches—many complications, most of which you will never use, but guaranteed to delight the gearhead in all of us. The “Affordable” option represents an entry-level watch for the new (or penny-pinching) enthusiast. Lastly, the “Conversation Starter” represents a piece that will draw eyes to your wrist, whether you like it or not. 

The Busy Watch: Mido Ocean Star Decompression Worldtimer ($1,310.00)

It doesn’t get much more complicated than the Mido Ocean Star Decompression Worldtimer; even the name is busy with impressive terminology and sci-fi vibes. The watch sports a hypnotically colorful dial that’s as vibrantly neo-vintage as it is functional. Of course, you’d never catch me in a situation where I’d need to time my ascent to the ocean’s surface to prevent fatal illness. Still, at least the watch also sports a nifty GMT function for the world traveler, and 80 hours of self-winding power reserve for the determined adventurer—or vicarious couch potato. 

The Ocean Star could have qualified for my Conversation Starter category due to its eye-popping color scheme and text-heavy bezel—as an ex-English major, I’m a sucker for any watch that makes me read—but its battle-ready status as a legitimate diving tool justifies its place as the Busy Watch pick for my list. Just make sure that you never actually have to use its partial-namesake function. 

The Affordable Watch: Omega x Swatch Mission to the Moonphase Full Moon ($310)

The Omega and Swatch collab that took the fashion world by storm (and swamped Swatch storefronts) in 2022 hardly needs an introduction, and few watches under the $500 mark are as instantly recognizable. But the MoonSwatch isn’t a cheap gimmick—the bioceramic material makes it perfect for casual summer (or Californian fall) wear, and its range of fun planetary themes opens the door to obsessive collecting and outfit-matching. I own the Saturn edition and have beat it to hell and back because it’s so damn light and easy on the wrist, though I swapped out the Velcro strap for a beige Alcantara equivalent, which gives it an upscale flair more befitting of its Omega roots. I’ve had more compliments on it than any other watch I own combined, and by the widest array of people—grocery store clerks, tech bros at coffee shops, and teenagers have all excitedly ogled my Saturn MoonSwatch, many of them sporting their own picks from the growing line of cheerful timepieces. 

The original lineup is slightly cheaper, but the new Moonphase editions feature everybody’s favorite beagle, Snoopy, and introduce even more fun easter eggs and a classic moonphase function. My pick is the all-white Full Moon version—just make sure to give the included strap extra cleaning attention, or your glamorous moon white may become more of a grim sun yellow. 

The Conversation Starter: Oris Pro Pilot x Kermit Limited Edition ($3,345.00 pre-owned) 

Speaking of anthropomorphic mascots, we’re going green with our Conversation Starter. The Oris Pro Pilot x Kermit Limited Edition features the eponymous green frog, who peeks out from the date window once a month to say hello (I wish he’d stay for longer, but it does mean that his cheeky visit is a little more special each time). It packs Oris’ Calibre 400 automatic movement with a 120-hour power reserve so that you can get your green on even after a weekend of the watch sitting on your dresser. 

The dial’s tennis ball-adjacent color is arguably visible from space, so you’ll have to be ready for some attention, and for a color-matching challenge should you try to plan an outfit around the watch. But its design is steeped in the elegant simplicity of other Oris Pro Pilot X watches, with sharp white indices and a brushed case and bracelet that almost succeed in calming down the neon dial. At 39 millimeters, the Kermit is also about the right size for most people—though it may look large on a muppet wrist. Be prepared to be the most enviable person in the room on the one day a month that Kermit pops into view, even if it means forgoing anonymity. 

Bonus: Casio toy watch rings (~$20-30 on eBay, plus shipping from Japan)

With a tiny sliver of the budget remaining, I’ve elected to go mini. A friend brought me back a pack of these little plastic model Casio watches from Japan, and even though they aren’t functional, the details are sure to delight. Each ring even comes with an acrylic display stand, so you can line these up on your shelf and pretend to be the world’s largest watch salesperson. Though the blind boxes can be tricky to ship from Japan, resellers on eBay and other sites sell single rings if you’re looking for a particular favorite Casio model.