Dials are the whole conversation in this row, so look at them in daylight before anything else. The Oyster Perpetual 31 ref 277200 in candy pink and the Oyster Perpetual 36 ref 126000 in lavender both come from the 2020 release of colorful lacquer dials, and they look best against plain denim and a white shirt. The silver ref 126000 is the calm one, and the 36 in candy pink is the same idea at a larger size.

The Datejust 36 pieces are the older, more traditional group. The ref 16234 has a champagne dial and a fluted white gold bezel on a steel case from 1995, which I would wear with a camel coat. The ref 16233 is two-tone with an ivory pyramid Roman dial, a quietly 1990s choice for a gold chain and a rib knit. The ref 116200 in rhodium has solid links and an engraved rehaut, the thin ring around the dial, and the blue Roman dial Datejust 36 on an Oyster bracelet is the one I would wear to the office.

Here is the authenticity check I would run on any of them. Ask for the reference and serial number, then confirm the watch has been inspected by an independent authenticator and look for the papers. Wind it, set the date and make sure the crown screws down fully. A bracelet that has stretched will rattle, so give it a gentle shake.

What I would skip: a pre-owned watch described only as good with no close photos of the case sides. The grade tells you very little without the lugs on screen.

Sports models and gold bracelets want a different test: put them on and check the weight. The Day-Date 36 ref 128238 in yellow gold has a green ombre dial with diamond markers and a President bracelet, and it is a lot of watch, so I would wear it with plain white and a pair of jeans. The two ref 18038 pieces, one with a white Roman dial from 1983 and one with a champagne dial from 1978, are the quieter, older option. Both sit on the same fluted bezel and bracelet.

Then the steel watches. The Submariner Date ref 16610 in black from 1993 has a black aluminum bezel and a 40mm case, and it works with a tee and a trench just as well as a swimsuit. The Submariner Hulk with its green Cerachrom bezel and green dial is the loud one, and I would let it be. For travelers there are two GMT-Master II choices: the Batman ref 126710BLNR with a black and blue ceramic bezel, and the ref 16710 Coke, whose aluminum bezel and discontinued colorway make it a favorite of mine. The Explorer 36 ref 124270 with a black Arabic dial is the plainest, and I think it is the most useful.

Check the bezel on every sports model. It should click crisply and line up with the marker at 12. On an aluminum bezel, small fading is normal for its age, while a bezel that spins freely with no click is worth another look.

Fading is not a flaw to me. A faded Coke bezel is just a watch that has been somewhere.

I would begin with the wrist. Try the 26mm, the 31mm and the 36mm on the same arm, because the size changes the whole feeling of a watch far more than the color does.

Next I would pick the metal: steel for everyday, two-tone for a bit of warmth, yellow gold for the days I want the watch to be the whole outfit. Then I would read the condition notes, ask about the papers and the bracelet, and choose the one I keep going back to.

The Datejust started as a fortieth birthday present from a company to itself. I would choose a Rolex the same way, as something I plan to keep wearing. If you want to keep browsing, I also put together Breitling Watches and Seiko Watches.