The world of the watch is changing, and at Gray and Sons, we pride ourselves on staying ahead of the curve. What once was just a convenient method of keeping the time has now become a highly desirable accessory or centerpiece to an outfit. Rather than focusing simply on functionality, watches have transformed into a fusion of form and function, bringing together elegance and style alongside timeless technology. While this shift in timepiece aesthetics can be considered recent, it draws its inspiration from one important piece of the industry – vintage watches.

Part of the allure of a vintage watch isn’t just that it has a particular design or style from a bygone area. Rather, it’s that it has stood the test of time, remaining coveted and distinguished although many other models have followed it. Vintage watches offer a glimpse into the timeless craftsmanship and techniques that go into their modern counterparts, all wrapped up with an unmatched style. These timepieces are an excellent way to add character to any outfit, with an undeniable charisma and charming aesthetic that will be uniquely yours.

But finding the right vintage watch can be a challenge. Between sorting through the library of available pre-owned watches and navigating the endless sea of styles to choose from, it can be difficult to find the right pieces to add to your collection. If you’re thinking about taking a dive into the world of vintage watches, we have you covered. Here are 19 of our favorite vintage watches to kickstart your collection in timeless style.

Vintage Cartier on Black Crocodile Strap

Vintage Cartier Manual Wind Watch

This timeless Cartier watch offers the best of both vintage inspiration and modern aesthetics, combining a classic rounded 31.5mm case with bold, lustrous 18K gold accents. A simple yet elevated black crocodile strap with plaque tang buckle completes the look.

Rolex Oyster Perpetual 6569 Stainless Steel Watch

Vintage Rolex Oyster Perpetual

There’s nothing quite like finding one of the most popular vintage Rolex models that’s still in mint condition. This Oyster Perpetual timepiece features signature design elements, including an engine-turned bezel with a unique cream dial for added appeal.

Patek Phillipe Ellipse 3598 Gold Manual Watch

Patek Philippe Ellipse

Ideal for any lover of true vintage style, this iconic Patek Phillipe Ellipse watch features bold art-deco inspired accents circa 1974 alongside a bold 18k gold mesh band. This timepiece is perfect for slipping on to make a sophisticated statement for any occasion.

Tiffany & Co. Pocket Watch

Tiffany & Co. Pocket

A truly vintage piece that will make any outfit, a Tiffany & Co. pocket watch is both elevated and playful at the same time. Circa 1920, this timepiece features a 44 x 44mm case with rounded case back and a crisp White Arabic numeral dial. 14k gold accents complete the look for a truly sophisticated feel.

Rolex Bubble Back 3348 Pink Gold & Stainless Steel Watch

Rolex Bubble Back

Is this one of the rarest vintage Rolex in the world that you can start your collection with ? The Rolex Bubble Back 3348 Pink Gold & Stainless Steel Watch is circa 1940 with plenty of eye-catching features. This rare Rolex watch features a 29 x 29mm case with round caseback and original Rolex presentation box shaped like a fan shell for a true wow factor.

Omega Constellation Stainless Steel Watch

Vintage Omega Constellation

When you’re looking for a modern yet vintage piece with undeniable style, an Omega Constellation is always a great option. This classic timepiece features a 34mm case with a silver stick dial and an iconic Omega “rice” style bracelet.

Ebel Cocktail 18k Gold Watch

Ebel Vintage Cocktail watch

Perfect for any true connoisseur of art deco inspired fashion, this eye-catching Ebel Cocktail watch flawlessly combines unique design elements and timeless style. This bold women’s watch features bold 18k gold with a statement-making bark finish and a playful rectangular design.

Rolex Air King Stainless Steel Watch

Vintage Rolex Air King

Any Rolex, pre-owned or new, is an elevated piece that will instantly make any look next level with subtle, timeless style. This Air King 5500 Stainless Steel 34mm Auto Watch is no different, featuring an iconic 34 x 34mm case with Silver Stick dial and a jubilee USA bracelet.

Omega Pocket Watch

Omega pocket watch

Another great vintage piece for the fan of a pocket watch, this Omega Pocket Watch combines a sleek cream dial with eye-catching 18k gold accents. Designed to be paired with any chain, this timeless pocket watch will make a sophisticated statement with any outfit.

Cartier Tonneau Dual Time Watch

Cartier Tonneau Dual Time

An innovative design with a lot of character, the Cartier Tonneau Dual Time 084-88 watch is both timeless and modern. This unique timepiece features sleek 18k gold with dual watch faces and an eye-catching blue crocodile strap.

Tudor Oyster Prince Stainless Steel Watch

Vintage Tudor Oyster Prince

Another favorite among lovers of used watches is the Tudor Oyster Prince. This sophisticated style features a classic rounded case with a black stick dial, contrasting accents and a sturdy stainless-steel bracelet with matching buckle.

Patek Phillipe Vintage Watch

Patek Philippe Vintage

Statement-making with a nod to iconic style, this Patek Phillipe ref. 3319/7 watch is a great eye-catching piece for any lover of vintage watches. This bold design features a square case set on a bold 18k gold bracelet with matching buckle for a unique appeal.

Cartier Tank Francaise Stainless Steel Watch

Cartier Tank Francaise

A favorite style of lover of modern and vintage watches alike, the Cartier Tank Francaise 2485 is a great addition to any collection. This timepiece features a sleek rectangular caseback with a clean white Roman numeral dial for a minimalist feel.

Chopard Pocket Watch

Chopard Pocket Watch

An iconic design with truly timeless appeal, the Chopard 9877 Pocket Watch in 18k white gold will add instant appeal to any look. This sleek and stylish used pocket watch offers an alluring 41 x 41mm case with silver stick dial and elegant features.

Patek Phillipe Vintage Manual Watch

Vintage Patek Philippe

Perfect for lovers of undeniably cool 1980’s style, the vintage Patek Phillipe ref. 2488 watch offers timeless sophistication and edgy aesthetics. This iconic timepiece features sleek 18k yellow gold with an eye-catching rectangular case and a white stick dial.

Bucherer Classic 18k Gold Watch

Bucherer 18k yellow gold “Bark”

When it comes to statement-making style, there’s nothing quite like a Bucherer Classic. This sophisticated style straight out of the 1960’s features iconic bark texture with a hinged dial cover and champagne dot dial for the perfect finish.

Bulova Vintage Stainless Steel Watch

Bulova Diver Compressor Brever

Sleek and sophisticated with a notable nod to modern style, the Bulova Vintage 317537/337462 Watch is a great wear-anywhere addition to kickstart any collection. This rare Bulova Diver Compressor Brever features a stainless-steel design with a 36 x 36mm case for eye-catching appeal.

Patek Phillipe Calatrava Watch

Patek Philippe Calatrava “Disco Volante”

Sometimes, when you find the perfect Patek Philippe for sale, you must jump on it immediately to add to your collection. This Patek Phillipe Calatrava “Disco Volante” watch is a perfect example, with a lustrous 18k composition with a sleek rounded case and eye-catching black crocodile strap for timeless appeal.

Rolex Daytona 6239 Watch

Rolex Cherry Daytona

Last, but certainly not least, on our list of must-have vintage watches is the Rolex Daytona. A beloved piece with a devoted following, this iconic design features a bold silver / black panda dial with a super rare first generation “Daytona” in red for the ultimate elevated appearance.

Vintage watches are more than just timepieces – they’re a statement. And what better way to start your collection than with a one-of-a-kind vintage watch? Whether you’re a seasoned collector or just starting out, trust Gray and Sons to guide you through the world of vintage watches and help you find the perfect piece to cherish for years to come.

With over 40 years of experience in the industry, we have built a reputation for being a trustworthy and reliable source for vintage watches. And with a 10-day return privilege and independent appraisals, you can shop with confidence knowing that you’re making a smart investment. Start your vintage watch collection today with Gray and Son’s.