Old Becomes New Again: Our Favorite Vintage Watches That Are Still in Style Today

When it comes to fashion and accessories, the word “vintage” can be either a trend or a taboo. But there are some pieces that simply never go out of style – and as luck would have it, vintage is decidedly in at the moment. Reporting on the 2025 Oscars, Vogue compiled a list of all the stars wearing vintage dresses on the red carpet, with standouts including Cynthia Erivo in ‘90s Alexander McQueen and Hailey Bieber in a Yves Saint Laurent piece from 1987. But when does vintage mean old, and when does vintage mean timeless?

Let’s take a closer look at the term “vintage” in the world of luxury watches. We’ll examine some of the perennial timepieces that have been manufactured for decades (some clocking in at nearly a century), holding their value all the while. We’ll also look at some newer timepieces that are inspired by the styles of yore. After all, fashion tends to be cyclical! So gear up and get ready to dive headfirst into Avi & Co.’s newest, hottest, oldest, glam-est watches…

A true “vintage” watch is one that has been preserved in a collection or passed down for generations and hails from another era. There’s a bit of disagreement on how old a watch has to be for it to be decidedly vintage, but overall, we’d say most of these pieces hail from around or before 1990. They could have one owner, or maybe they have been passed around a bit. Maybe they are still produced, or maybe the line has been discontinued altogether. Either way, a vintage watch is at least 30 years old.

Remember: A watch does not have to be discontinued to be vintage. For example, vintage Rolex Datejust models are a popular purchase. The watch was first introduced in 1945 but is still manufactured today. A Datejust from 1945 is certainly vintage, as is a Datejust from 1960, 1972, or 1989. But you can also buy a brand-new Datejust that looks vintage or is inspired by the original designs and dials of the collection!

Many people wonder, if a watch is discontinued, can I still buy it? The short answer is yes… and no. You cannot buy a discontinued watch directly from the manufacturer, as they do not make or sell it anymore. But you can buy a discontinued watch on the secondary market from trusted sellers like our team at Avi & Co.

On the secondary market, individuals can buy, sell, trade, and consign their timepieces to curate the watch collection of your dreams. When you work with a secondary market watch expert like Avi & Co., you’ll gain access to our robust network of watch world connections – in other words, if you’re looking for a particular timepiece (whether or not it’s vintage), we can more than likely source it for you.

For example, take a look at this video review from our loyal customer Nick, who has purchased numerous watches from Avi & Co. He wanted a particular Patek Philippe Aquanaut model, and the sales team at our Miami store went above and beyond to source exactly the watch Nick was hoping for. Watch the video to hear what Nick has to say about his experience.

Some vintage watches are still functional, while others might have suffered damage that renders them defunct. At Avi & Co., we only sell fully functional, certified original timepieces. With us, you’ll never have to worry about problems with your watch or a knockoff that you only discover down the road. We even have in-house watch repair services to give you total peace of mind if anything does go wrong.

When you buy a vintage watch with Avi & Co., you can rest assured that you’ll walk out of our store with a working timepiece that you’ll be able to enjoy for a lifetime.

Wondering which timepieces are the hottest vintage and vintage-inspired options on today’s market? We’ve got you covered. Check out our comprehensive list right here!

While the Rolex GMT-Master II line was introduced in 1982, it was not until 1999 that the original GMT-Master collection was officially discontinued. This specific timepiece hails from 1984 and would have been initially manufactured with a matt black dial with painted tritium indices. Pieces made after 1986 have glossy dials with applied white gold tritium-filled indices – which this watch now exhibits after a replacement performed by Rolex during routine servicing.

The watch’s dial exhibits minor hairline scratches, contributing to a sought-after "spider dial" appearance, which has gained considerable popularity among vintage watch aficionados. While the bezel has some light scratches throughout its life, it maintains vibrant colors indicative of its age. Overall, this piece remains in good condition, making it an ideal choice for those seeking a vintage watch suitable for daily wear.

As a brand that has been around since 1839, it’s no surprise that Patek Philippe has plenty of vintage-worthy watches in its almost two centuries of operation. While the Patek Philippe Calatrava featured above is not vintage itself, it evokes the look of the original Calatrava line from the 1930s. The Calatrava was first introduced in 1932 and is a flagship model for the Swiss brand. It exudes timeless class and elegance and was apparently inspired by the popular Bauhaus movement of its time. It was also a favorite of renowned Spanish artist Pablo Picasso, who was often photographed wearing a yellow gold Calatrava with a brown leather strap!

Since the 1930s, Patek Philippe has unveiled numerous variations on the classic Calatrava design, introducing references with metal bracelets, adding different precious metals to the rotation, and experimenting with unique designs, like the Calatrava pilot’s watch. As this model approaches its 100th anniversary, it is a good time to get your hands on this memorable piece.

Other Patek Philippe watches worth noting for vintage value are any of its pocket watches and the prized Patek Philippe Nautilus 5711, which was discontinued in 2021 and has only boomed in popularity since then.

Speaking of Patek Philippe, there’s another incredible watch from this Swiss brand in stock at Avi & Co. that we have been drooling over. The Patek Philippe Gondolo Cabriolet, Reference 5099RG, was launched in 1999 at Baselworld – but eagle-eyed horological enthusiasts quickly recognized it as an homage to a watch from way back in the 1920s. The “Cabriolet” component of the name refers to the cover of the watch, which you can lift up and down to cover or reveal the watch’s face. It is a relic of a time when glancing at one’s watch was considered disrespectful to one’s companion – therefore, the cabriolet was introduced as a deterrent.

After its launch in 1999, this timepiece was produced for eight years and is now discontinued. The model is much-loved by collectors, who appreciated the turn-of-the-century addition to Patek Philippe’s repertoire and its harkening back to the olden days. If you’re looking for a wearable, distinctive addition to your watch collection, don’t miss out on this unique piece, which is sure to be a conversation starter when you show it off.

The Rolex Oyster Perpetual is a classic entry-level Rolex watch that first hit the market in 1926. As we gear up for a century of loving this gorgeous, iconic timepiece, it’s fair to say that adding an Oyster Perpetual to your collection is never going to be a bad move. There are certainly some references that are considered paragons in the vintage watch world (for instance, the Reference 1002) – but frankly, the line hasn’t changed that much since its inception. And we like it that way! Why fix what’s not broken?

An Oyster Perpetual watch is also a fun way to kick off or fill out your watch collection because there are so many fun dial colors and variants. The forest green dial pictured above is a crowd favorite, but Rolex also makes turquoise, rosy pink, vermilion, marigold, and even a “celebration” dial that combines all of those colors in a whimsical pattern. For those looking for something more understated… Yes, there are black and silver dials too!

At Avi & Co., we are a trusted secondary market reseller of some of the world’s most famous watch brands. From Richard Mille to Rolex and from Audemars Piguet to Patek Philippe, you can find the most coveted timepieces on Earth in our three showrooms. We have locations in New York City, Aspen, and Miami – so wherever you call home, there’s an Avi & Co. boutique near you!

Schedule an appointment today to visit us in person. We can’t wait to meet you!