Many new collectors who are, perhaps avid readers of Hodinkee or some of the other watch collecting/journalism sites, set off in search of the largest vintage piece that they can find. That’s fine, and generally, larger sizes are valued more highly. Though, I’d also point out that the opposite end of the spectrum, the truly tiny chronographs, such as the “Boy’s Sizes” at around 30mm are incredibly collectible (and valuable) precisely because of their relative scarcity and because of the technical expertise that was required to shrink such a complicated watch movement down to that small of a package.
I’d encourage you to stop and think about this for a minute. If you were writing the article, there’s only so many quantitative characteristics of a watch that you could describe. Then you get into the very subjective personal assessments of aesthetics. So it’s no wonder that many of these articles seem to place an inordinate amount of emphasis on a watch’s size. Whether it’s a modern monster that engulfs your wrist at 44mm or a more modest vintage piece at 33mm. The difference on paper, can seem, well, enormous.
Hang out amongst vintage collectors for a little bit, and you’ll definitely hear the topic of size come up, but it’s not the be-all, end-all of desirability. In fact, it’s probably one of the lessor factors that contributes to a piece’s value. If you’re interested in Universal Geneve, for example, try on one of the Compax chronographs in 33mm. Try on one of the later, waterproof Tri-Compax pieces in a 35-36mm example. And sure, try on a 37mm Tri-Compax from the 1940s-50s as well. I think what you’ll find is that unless you have unusually large or small wrists, the size of the piece sort of evaporates when it’s on your wrist. The 33mm chronographs can look downright elegant on a nice strap–pushing the bounds of what would be considered a “dress watch,” for example.
Try things on. Figure out what works for you!–and discover what your own preferences are for the size of a watch that goes on your wrist.