The first thing to talk about when talking about watches is one's definition of "watch". For some people a watch is simply anything that tells time, including a phone. For some it has to have an analog display. For some it has to be mechanical (manually- or self-wound; not battery powered). And for some it has to have an in-house movement and be meticulously assembled and finished by a master craftsperson. When I talk about watches I generally hover somewhere around the top two tiers, but occasionally my wandering eye will see something compelling in a broader definition of "watch". There is, of course, no definition that is more correct than the others, so there's no point in being too rigid and dogmatic about what is and isn't a "real" watch. Just enjoy them for what they are (which is whatever you want them to be).
To deep-dive into learning about watches from people who genuinely know what they're talking about, start clicking around Hodinkee and you'll be an expert in a matter of hours.
But here's one guy's opinion on watches he really, really likes (and wants):
10 // Vintage Omega Seamaster - My first "real" watch is a late-60s Omega Genève that has had its dial repainted, its caseback replaced with a Seamaster's "monster", and keeps impeccable time any more only when it wants to. But I love it in spite of and because of its quirks and I highly recommend vintage Omegas for their looks and for their relatively accessible price point for high-ish-end watches.
09 // Heuer Camaro - It has great lines, a good racing heritage, and the distinctive cushion shape of the case falls squarely in the Goldilocks Zone between the very-round Carrera and the too-square Monaco.
08 // Ochs & Junior Two Time Zones - I really dig O&J's fresh, modern approach to watchmaking and the customization process for their watches. The Date and Moon Phase models are more aesthetically interesting to me, but I am genuinely annoyed by calendar complications on watches and I would (hopefully) use the 2nd time zone option more frequently.
07 // Casio G-Shock GWB5600BC-1B - One of these things is not like the others. This G-Shock model specifically checks all of the boxes for me. It's a tough-as-nails G-Shock, is incredibly badass blacked out, is solar powered so there's no battery to change, and it connects to your phone via Bluetooth to calibrate its time and for adjusting settings, alarms, etc., which is nearly impossible on a regular G-Shock.
06 // Rolex GMT-Master (II) - An authentic pilot's watch developed in the 1950s, but now it's essentially a Submariner that keeps time across three time zones and has some great bezel color schemes (are you an all-black or a Batman, Pepsi, Coke, or Root Beer kind of person?). Slightly more interesting and rare than the ubiquitous Subs, and slightly more purposeful.
05 // IWC Portuguese - About as clean of a chronograph as you'll ever find, backed up by an impressive legacy in Swiss watchmaking. The Portugieser falls nicely on the dressier side of watches, but would still look right at home with its tee shirt wearing owner palming an In-N-Out Double-Double.
04 // Patek Philippe Calatrava Small Seconds - It's so incredibly simple and elegant and thin and luxurious and understated and is absolutely perfect in every way.
03 // Jaeger-LeCoultre Reverso - The original rough-and-tumble sports watch from the 1930s has aged into a very stately and dignified gentleman. I love that the watch face can be flipped over and protected from rogue polo mallet strikes behind its steel engravable caseback. I have no idea what I would actually have engraved on the case, but turning a skilled engraver loose back there would be fun.
02 // Omega Speedmaster Professional Moonwatch - Any manually-wound version (with 3 chronograph registers and no date, though) from 1957 to today would be perfectly fine with me. I love that they look like purpose-built tools for engineering and somehow still manage to feel uncluttered despite the sheer amount of information that is contained within the dial and bezel. And apparently they went to the moon or something...
01 // Rolex Explorer I - If I could only wear one watch for the rest of my days, this would be it. Without question. It has all of the cache, reliability, prestige, and durability of a Rolex, but in a less-obvious, less-is-more package compared to the Submariners. It's a more manageable size and more versatile shape than Subs, and is WAY more attractive.
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Out of my league but still in my heart: Rolex Daytona Paul Newman, Omega Speedmaster Silver Snoopy, H. Moser Endeavor Vantablack
Honorable Mentions: Omega Railmaster, Heuer Autavia, Blackout Rolex Milgauss, Timex Marlin Snoopy Flying Ace, Apple Watch, Tudor Black Bay 58 Bronze, IWC Pilot Spitfire (and the Hodinkee version)