With the chaos of the holiday season only just behind us, it can leave one scrambling to remember what day of the week it is and pausing just a bit too long when writing down the year. With that in mind, here are six pre-owned watches in the Hodinkee Shop that can reliably tell you it’s Monday, Tuesday, or Friday, and one that can even tell you what year it is, so you can kick off the new year in a fashionably synchronized way.
Tudor Day-Date Prince 76200
A date wheel is a common complication, and while adding the day of the week may give some clarity to your calendar, it will also add some level of complication to the watch itself. While Rolex’s version of the Day-Date may be more famously known by the moniker “The President” – for how common it is on the wrists of US leaders – the Tudor version is a little bit easier to get your hands on. Modeled after the Rolex version, the Tudor Date+Day puts the day of the week across the 11 and one-hour markers for clear visibility. The case shape and smooth bezel are taken from Rolex as well, but Tudor put its own five-link bracelet and textured dial on this watch.
Breitling Galactic 44 A45320

The often-overlooked Galactic from Breitling puts the day-date complication in a watch that’s ready for exploring. The rider tabs on the bezel and steel case might have you thinking this is a Chronomat, but this is a watch built for the outdoors instead of the cockpit. The rehaut has a compass layout, and the uni-directional bezel with 200m of water resistance combines to make this a functional dive watch. The 44mm large steel case will prove to be a formidable companion on your next camping trip.
Omega Speedmaster Day-Date Chronograph 3220.50.00
The Speedmaster Day-Date may come from before the days of co-axial escapements as the Omega standard, but that doesn’t mean it doesn’t pack a horological punch. This watch starts with the DNA of a Speedmaster with twisted lugs, a black tachymeter bezel, and three register chronograph – all with a different layout. On top of the tried-and-true design is a day and month indicator inside the 12 o’clock sub-dial and an extra hand that works as a pointer date. The pointer date hand takes 31 days to circle the watch’s dial, pointing to the date of the month printed on the outer edge of the dial along the way. Having the date, day, and month all tracked on the dial is referred to as a “triple calendar” and is a moonphase away from a complete calendar.
Omega De Ville Annual Calendar 433.
Moving up the complications ladder is the Omega De Ville Annual Calendar, with an opaline silver dial that features a month and date window. The simplicity of the display hides what’s going on beneath the dial, where the movement mechanically tracks when to jump ahead on the 30th or 31st of each month. Only at the end of February do you have to move the date forward to March 1st. This once-a-year change is why this complication is referred to as an annual calendar. To match the high-level complications on the dial, there are 18k white gold hours markers and hands. The hands have even been oxidized to give a slick black sheen to them. This is a watch ready to be worn to the office, on the weekend, or to a nice evening out all year round.
Breitling Super Chronomat 44 Four-Year Calendar I19320
Another rugged Breitling makes the list, but this time, the rider tabs correctly tell you it’s a Chronomat. The dial has a lot going on in each of the four sub-dials. First, this is a chronograph with an internal tachymeter scale and sub-dials that work accordingly. Each sub-dial does have a second hand, with the one at six o’clock telling the day, the nine o’clock dial pointing to the month, and the 12 o’clock indicating the date. With the addition of the moon phase at three o’clock, this Breitling is a complete calendar, but that’s not the last trick up its sleeve. The movement is a four-year calendar, which means that, unlike an annual calendar, this watch will jump forward on February 28th to March 1st without any fiddling around with the crown. Only once every four years during a leap year will this watch have to be reset.
IWC Big Pilot Antoine De Saint-Exupery Perpetual Calendar Limited Edition IW5038-01
IWC Big Crown arrives with none other than a big complication. This 46mm wide watch leaves plenty of space for each sub-dial to tell the day, date, and month. The moonphase on the top completes the traditional calendar. It’s the small four-digit date near the seven that reveals that a little more is happening underneath the surface. This is a perpetual calendar, which is often considered one of the hardest complications to make. Once the calendar on this watch is set, it will accurately jump forward at the end of every month, also keeping track of leap years. If it’s February 28th or 29th, the gearing will know and jump forward accordingly. The only exception is that years that are divisible by 100 and not by 400, which is when a leap year is skipped. One of these years is coming up in 2100, so if you keep the seven-day power reserve topped off and have taken good care of the watch, you will have to add your own input to the calendar in 77 years.