Art deco. The Great Depression. Zoot suits. Shag carpet. For better or worse (we could have done without the crippling depression and avocado-green rugs, but hey), each of these brings a distinct decade to mind. And whether you’re drawn to a good jazz-era Homburg a la the Roaring Twenties or James Dean’s era of teenage disillusionment, there’s sure to be an epoch that catches your eye.

However, you can’t fully appreciate these time periods until you’ve explored the vintage watches that tick, tick, ticked the minutes and hours away, bringing the world closer and closer to the next innovative decade. From the forefathers of the classy modern Rolex to the tough and practical predecessors of today’s dive watches, these classic timepieces captured the essence of their decades while pushing watch evolution forward.

1920s: Rolex Oyster and Cellini Prince

Rolex roared through the ‘20s with a wealth of (what are now) classic vintage timepieces. While flappers flapped and prohibition prohibited, Rolex released the rectangular Cellini Prince timepiece, which, in addition to paying homage to the art deco inspiration of the era, was the first watch to become chronometer certified. With a large sub-dial to count seconds, this “doctor’s watch” released in 1928 predated the use of center seconds and are, quite frankly, drop-dead elegant. What these vintage timepieces possess in good looks though, they lack in durability.

You wanted durability? Enter the Rolex Oyster classic watch.

First debuted in 1926, this collectible watch was the first waterproof watch. To prove just how good the hermetic seal was, English swimmer Mercedes Gleitze wore an Oyster for her grueling 10-hour swim across the English Channel in 1927. (Not missing a beat, Rolex took out a full-page ad on the front page of the Daily Mail the very next day, boasting of the success of the three-part waterproof case. Solid marketing team.) Essentially, this vintage watch was the precursor to the modern sport watch—though its echo of art deco is decidedly more attractive than the sports watches of today.

1930s: Jaeger-LeCoultre Reverso

The Threadbare Thirties heralded in the Great Depression, and were, to put it lightly, a rough time in the U.S. Perhaps not quite as tough were the problems faced by polo-playing British army officers, whose watches kept being damaged by rogue polo mallets and errant balls. (What suffering they endured!)  Luckily, in 1931, the Reverso hit the market with a watch case that allowed the watch to be flipped over while still on the wrist. Once the watch was flipped, a protective metal back case kept it safe from polo accidents. The strong back combined with a face that could be dubbed an art-deco masterpiece leaves this watch as a top contender for best in form AND function.

1940s: Patek Phillipe 1518 in steel

You can circle the year 1941 on the calendar: That was the year the first perpetual calendar with chronograph debuted on a timepiece. The Patek Phillipe 1518 watch (and the 2499 version) were in fact the only two perpetual calendars with chronograph for the better part of 50 years. The 1518 version of the collectible watch came in several colors to best match your zoot suit; customers could choose from steel or yellow or rose gold, with steel being the rarest: In fact, there are only four known worldwide (one of which sold at auction for a mere $11,136,642 in 2016). If you’re willing to settle for a 1948 rose gold version, you’re in luck: They can be had for a steal at around $1.5 million.

1950s: Breitling Navitimer “Pre-806” with Valjoux 72

 
The Fifties took flight with the Breitling Navitimer 806. Believed to have been released in 1954 for the Aircraft Owners & Pilots Association, the Navitimer watches provided pilots with every bit of info they might ever need about navigation (“navi-“) and time (“timer”) in the pre-digital age, thanks to a slide-rule bezel. Essentially, they crammed a lot of information into one tiny watch face—and apparently, it worked! The early (read: most coveted) versions of the 806 (sometimes called the “pre-806”) vintage watches feature the Valjoux 72, which is the same movement that was integrated into some of the vintage Rolex Daytonas. Couple this with a bowling shirt and some penny loafers, and you’re truly channeling the decade—though you’ll pay a pretty price. 806’s run about $4K, while a pre-806 will cost you at least $25K.

1960s: Jaeger-LeCoultre Polaris

While the Peacock Generation dominated the fashion world with their bold new looks, in 1968 this vintage watch kept things simple—at least at face value. While the Polaris’ watch face didn’t stand out, it was literally what was inside that counted. This vintage watch was the first diving watch with a mechanical alarm, and features a triple case to optimize sound transmission underwater (the outer case back has 16 holes in it so that the alarm can be heard more easily). Only 1,714 of these bad boys were ever made, so they’re a sought-after collectible watch and a perfect complement to your lava lamp and Beatles albums.

Every decade brought new styles (again, for better or worse—should Glenn Urquhart suits or checkered linoleum really have been a thing?) and new developments in classic watches, leaving us with an exciting array of collectible vintage timepieces to choose from. Whichever decade you prefer, these cool (groovy, swell, keen, bee’s knees) vintage watches clocked in with the vibe of the decade while hinting at the style and ingenious innovation to follow.