There’s nothing quite like slipping on the perfect watch to complete your outfit. Whether you’re getting ready for an important meeting at the office or heading out for an evening with someone special, the right timepiece can add instant elevation and class to anything that you wear.

Having the right timepieces at your disposal to slip on for any occasion is a long and thoughtful process that often involves countless hours of searching for the right pieces at the right prices to suit your taste and budget. And once this collection is complete, you’ll have the perfect array of styles to reach for to suit any upcoming occasion.

But, finding the right pieces to start or add to your collection can be a challenge. Between sifting through endless new and used luxury watch styles, it can be difficult to determine which pieces are worth the investment. At Gray and Sons, we understand this struggle and are here to help. Whether you’re new to the world of watch collecting or simply searching for more affordable options to round out your timepiece collection, we have the perfect pieces for you. Here are 17 of our favorite watch pieces to start your watch collection under $20k.

The Rolex Datejust 16018 Watch

Rolex Datejust

When it comes to luxury watches, there is no name more synonymous with iconic style than Rolex. This used Rolex Datejust is no exception, offering a beautiful 18k yellow gold construction with a stunning 36 x 36mm case with round caseback and Silver Stick dial.

The Hublot MDM 1393.2 Watch

Hublot MDM

Designed with a nod to vintage style, this elegant pre-owned Hublot MDM 1393.2 Watch is the perfect timeless addition to any collection. This piece features an original Mother of Pearl dial set in a silver- and gold-plated bezel with a 25 x 25mm case with round caseback.

The Chanel Mademoiselle H0007 Watch

Chanel Mademoiselle

There is truly no brand like Chanel. Forever entwined with luxury fashion, Chanel offers the perfect selection of timeless watches to add to any collection, including this beautiful Chanel Mademoiselle H0007 Watch. This pre-owned Chanel watch features an eye-catching 22.4 x 22.4mm case with a square caseback carefully set on five strands of shimmering pearls.

The Tag Heuer Aquaracer WAF1110 Watch

Tag Heuer Aquaracer

A favorite timepiece amongst collectors around the world, the Tag Heuer Aquaracer watch effortlessly combines function and fashion. This stylish watch features a durable stainless steel composition with a striking 39 x 39mm case with round caseback and Black Stick dial.

The Franck Muller Casablanca 7500 Watch

Franck Muller Casablanca

If you’re searching for a timeless style that exudes elegance to add to your watch collection, there is no better timepiece than a Franck Muller watch. This unique pre-owned Franck Muller watch is the perfect example, offering a stunning 18k yellow gold composition with a 28.5 x 32mm case with Tonneau caseback and silver Roman Numeral Dial.

The Cartier Tank Americaine Watch

Cartier Tank Americaine

The Cartier name is interchangeable with elegance in the world of luxury watches. This pre-owned Cartier Tank watch is a great example of this thought, with a truly timeless 27 x 45mm 18k yellow gold case with rectangle caseback, Silver Roman Numeral & Arabic Dial and bold lug detailing.

The Patek Philippe Calatrava 3820 Watch

Patek Philippe Calatrava

One of the most respected names in the world of luxury watches is Patek Philippe. This pre-owned Patek Philippe Calatrava watch is the perfect piece from this renowned brand to add to your collection, with a sophisticated 32 x 32mm case with round caseback with White Roman Numeral dial on a sleek leather strap with original 18k tang buckle.

The Chopard Happy Diamond Watch

Chopard Happy Diamond

Perfect for adding a little bit of color and sophisticated shimmer to any outfit, the Chopard Happy Diamond 207233 Watch features an elegant Mother of Pearl hour display surrounded by a trendy transparent outer dial that perfectly showcases 12 floating, sparkling diamonds.

The Gio Manaco Hypnos 11/50 Watch

Gio Monaco Hypnos

An elevated style from Gio Monaco is the perfect subtle yet statement-making piece to round out any timepiece collection. This incredibly rare Gio Monaco Hypnos Geneve Chronograph watch features a bold 45x 45mm 18k rose gold case with round caseback and Black Roman Numeral dial.

The Omega Seamaster Planet Ocean Deep Black Watch

Omega Seamaster Planet Ocean

There’s nothing quite like adding a bold pre-owned Omega Seamaster watch to your wrist before heading out for an important occasion. This Omega Seamaster Planet Ocean Deep Black Watch is the perfect option to suit any occasion and sense of style, with a striking 45 x 45mm case with round caseback and Black Stick dial on a comfortable rubber strap.

The Tiffany & Co Classic Champagne Dial Watch

Tiffany & Co. Classic

Circa a la 1970’s, this bold vintage Tiffany & Co. watch is the perfect statement-making piece to add to any outfit. This pre-owned Tiffany & Co. Classic Champagne Dial Watch features a stylish 18k yellow gold link bracelet with a 35 x 20mm case with rectangular caseback and a Champagne No Market Dial for a sophisticated appearance.

The Rolex Submariner Kermit 126610LV Watch

Rolex Submariner Kermit

Another timeless design from the Rolex Watch Company collections, the Rolex Submariner effortlessly combines function and style. This used Rolex Submariner Kermit Watch is in like-new condition and features a durable stainless steel construction with a 41 x 41mm case with round caseback, a Black Stick Dot Dial and green ceramic bezel.

The Breitling Transocean Chronograph RB0152 Watch

Breitling Transocean Chronograph

Effortlessly elegant with a sense of modern sophistication, this Breitling Transocean Chronograph Watch is the perfect timepiece to round out any collection. This stylish used Breitlin watch features 18k rose gold and a 43 x 43mm case with round caseback and Silver Stick Dial.

The Bvlgari Parentesi BJ 01 Watch

Bvlgari Parentesi

Ideal for any collector who’s searching for a bold, statement-making style, this used Blvgari watch offers a truly unique appearance and unmatched sophistication. This Bvlgari Parentesi BJ 01 Watch features shimmering 18k yellow gold and sparkling diamonds with a 20 x 20mm case with round caseback and Pave No Marker dial.

The Patek Philippe Gondolo 5024 Watch

Patek Philippe Gondolo

Another perfect example of a must-have pre-owned Patek Philippe watch style, this elegant timepiece is sophisticated yet highly wearable. This Patek Philippe Gondolo 5024 Watch features a 30 x 38mm case with rectangular caseback and White Arabic Numeral Dial on a sleek black crocodile leather band.

The Chopard Imperial 8531 Stainless Steel Watch

Chopard Imperial

Minimalist with an elegant appeal, this Chopard Imperial 8531 Watch is the perfect addition to any timepiece collection. This pre-owned Chopard watch features a bold Mother of Pearl dial in stainless steel with a sophisticated 40 x 40mm case with round caseback for the ultimate in wear-anywhere elegance.

The Cartier Trinity WG2001S8 Watch

Cartier Trinity

A playful yet elevated style, this used Cartier watch is a great choice for dressing up any outfit to suit any occasion. This Cartier Trinity WG2001S8 Watch features shimmering 18k yellow gold with a tri-color diamond bezel and a sleek 26.7 x 26.7mm case with round caseback and Beige Guilloche Dial.

We hope our article on watch pieces to start your watch collection under $20K will help you with your journey of building a formidable watch collection. The right timepiece can truly make all of the difference in what you’re wearing, whether you’re heading to the office for an important presentation, or enjoying a date night with your significant other. Finding the right pieces to add to your collection can be a challenge, but Gray and Sons is here to help guide you through the world of luxury watches and help you find the perfect pieces.

With over 40 years of experience in the industry, we have built a renowned reputation for being a trustworthy and reliable source for luxury watches. And with a 10-day return policy and independent appraisals, you can shop with confidence knowing that you are making a smart investment with us. Start your luxury watch collection today with Gray and Sons.