Let’s say you’re on a binging kick, and not of reality television or another true crime series, but good old fashioned vintage watch content. In the year 2020, admirers of horology have never had more captivating information on this revered craft at their disposal, naturally making many want to get in on the game for themselves. With every article you read and video you view, your desire for a great vintage watch is only intensifying, but with so many options to choose from, making the leap into the collecting world can be an understandably daunting task. Today, we’re here to offer up a few pieces that not only rank among our favourites, but represent some of the best buys imaginable for those looking to start a collection that’ll stand the test of time.

Rolex Datejust

Though the brand’s sports offerings enjoy unparalleled fanfare within their class, there’s really no more versatile and iconic Rolex model than the famed Datejust. Introduced in 1945, the Wilsdorf timepiece immediately made a splash thanks to the impressive combination of both an automatic movement and a date complication, neatly positioned at the three o’clock marker for easy reading. Following the first reference (Ref. 4467), the watch would go on to realize a collection of references executed in both precious metals and robust stainless steel, bearing a varied range of dials, bezels and bracelets. The extensive number of configurations made the watch a hit with those looking to express their individuality, all while maintaining the arguably perfect, no nonsense aesthetics of a 36 mm Oyster.

Of the bunch, the gold fluted bezel-fitted Ref. 1601 is one of the best ways to go, and one of the best buys in vintage watches, to boot. As the market has continued to progress, this reference remains attainable to many, while still possessing all the celebrated facets that have made vintage Rolexes so popular. Powered by the in-house Cal. 1570, this Datejust is about as reliable a timepiece as you can get, and with modern references taking direct inspiration from it, this watch is literally never going out of style. Every important collection has a Datejust, and upon seeing a noteworthy example, it’s easy to see why.

Omega Speedmaster Professional

Best known as the “Moon Watch,” the Speedmaster Professional is truly one of the greatest values in horology, and one of the ultimate picks for a first fine watch. That’s because it has everything going for it and then some. Timeless styling? Check. High grade chronograph caliber under the hood? Check. A singular reputation for being the first watch worn on the moon itself during NASA’s Apollo 11 mission of 1969? You know it. Simply put, it’s one of the greatest watches ever made, and the perfect candidate for a one watch collection in the eyes of several seasoned aficionados.

Throughout its production, the Speedmaster saw a number of changes, but never did the watch stray from the manufacture’s original vision. Omega progressed the line through the incorporation of new calibers, beginning with the Cal. 321, and later the Cal. 861 and subsequent Cal. 1861. The Speedy was also evolved by way of experimentation with minor design updates and material adjustments, most notably seen through the change from straight to twisted lugs, along with the departure from hesalite to sapphire crystals. Professional references from the 1990s can still be had for serious deals, making them attractive propositions to those just getting started in watches.

Jaeger LeCoultre Triple Date

Last but not least is perhaps a less obvious pick, but a terrific one nonetheless. Within the industry, Jaeger LeCoultre is well known as the “watchmaker’s watchmaker,” largely as a result of their history of producing quality movements for top tier brands like Patek Philippe, Audemars Piguet, IWC, and more. Though they have a number of stunning time-only calibers to their name, the brand is best known for their rich history of complicated watches. To the delight of many new collectors, many of these early complications can still be had without breaking the bank, including their stunning Triple Date Calendar.

As its name would suggest, the Cal. 451/A-powered watch touts a full, triple function calendar complication, displaying the day, date, and month, using a series of apertures and hands. All this is set using the crown and two recessed pushers found on the case’s edge, keeping the design elegant despite its several functions. With teardrop shaped lugs and multi-coloured dials, these watches have all the vintage charm you could ask for, and tuck neatly under a shirt cuff at 36 mm across. Much like the two previous watches, it’s genuinely hard to beat one of these 1940s complications for the money.