Dress Watches

Rooted in tradition and built for sophistication, dress watches are the cornerstone of elevated wristwear. Whether worn with a tux or tailoring, their sleek design and minimalist details never go unnoticed. At Grand Caliber, discover an expert-curated mix of new & preowned watches designed for evenings out, boardroom presence and everything in between.

192 products

Vintage

Rolex Datejust 36 16233

$7,245.00
Watch Only | 1994 | 36mm

Vintage

Rolex Day-Date 36 18238

$21,735.00
Watch Only | 1996 | 36mm

Montblanc Meisterstuck Star GMT 101638

$8,800.00
Watch Only | 42mm

Cartier Santos De Cartier WSSA0039

$8,540.00
Watch, Box, Papers | 2024 | 39.8mm

Vacheron Constantin Fiftysix 4600E/000A-B442

$14,805.00
Watch, Box, Papers | 2026 | 40mm

Vintage

Cartier Santos 2319

$6,210.00
Watch Only | 29mm

Rolex Datejust 36 126200

$9,315.00
Watch, Box, Papers | 2022 | 36mm

Vintage

Rolex Datejust 1601

$9,315.00
Watch Only | 1964 | 36mm

Rolex Day-Date 40 228235

$43,470.00
Watch Only | 40mm

Vintage

Rolex Datejust 1603

$5,175.00
Watch Only | 1970 | 36mm

Cartier Tank Must Black WSTA0071

$4,090.00
Watch, Box, Papers | 2022 | 29.5mm

Rolex Sky-Dweller 336934

$25,360.00
Watch, Box, Papers | 2026 | 42mm

Vacheron Constantin Overseas Automatic 4520V/210A-B483

$30,535.00
Watch, Box, Papers | 2025 | 41mm

Rolex Land Dweller 127234

$20,700.00
Watch, Box, Papers | 2026 | 36mm

Rolex Datejust 41 126333

$18,115.00
Watch, Box, Papers | 41mm

Patek Philippe Annual Calendar 5205R-011

$58,995.00
Watch, Box, Papers | 2024 | 40mm

Vintage

Rolex Air-King 5500

$4,140.00
Watch Only | 1969 | 34mm

Maurice Lacroix Masterpiece Double Retrograde MP7018-PS101-110

$3,105.00
Watch Only | 43mm

Rolex Datejust 36 126233

$20,700.00
Watch, Box, Papers | 2025 | 36mm

Jaeger-LeCoultre Reverso Tribute Monoface Small Seconds Q713842J

$11,385.00
Watch, Box, Papers | 2024 | 45mm

Rolex Datejust 41 126300

$10,870.00
Watch, Box, Papers | 2024 | 41mm

Glashütte Original PanoLunar Inverse 1-91-04-01-03-62

$41,400.00
Watch, Box, Papers | 2025 | 42mm

Omega Seamaster Aqua Terra 220.10.41.21.03.001

$5,385.00
Watch, Box, Papers | 2019 | 41mm

Vintage

Rolex Day-Date "President" 118238

$25,360.00
Watch, Box, Papers | 2000 | 36mm

Rolex Datejust 41 126333

$15,010.00
Watch, Box, Papers | 2021 | 41mm

Rolex Datejust 36 116234

$10,350.00
Watch Only | 36mm

Grand Seiko Heritage Collection Soko Shadow SBGA429

$5,175.00
Watch & Box | 2024 | 39mm

Grand Seiko Evolution 9 Hi-Beat 36000 SLGH027

$8,800.00
Watch, Box, Papers | 2025 | 40mm

Gerald Genta Arena Bi-Retro

$25,875.00
Watch Only | 45mm

Cartier Santos De Cartier WSSA0018

$7,245.00
Watch, Box, Papers | 39.8mm

Omega Museum Petrograd 1915 5703.30.01

$9,835.00
Watch, Box, Papers | 2007 | 43mm

Cartier Tank Francaise W51008Q3

$4,660.00
Watch & Box | 20mm

Rolex Datejust 41 126334

$19,665.00
Watch, Box, Papers | 2026 | 41mm

IWC Chronograph Portuguese Rattrapante IW371202

$8,125.00
Watch, Box, Papers | 2002 | 41mm

Grand Seiko Elegance Hi-Beat 36000 GMT SBGJ219

$5,175.00
Watch, Box, Papers | 2018 | 39.5mm

Cartier Pasha Chronograph W3108555

$5,695.00
Watch, Box, Papers | 2008 | 42mm

Grand Seiko Elegance SBGW281G

$4,140.00
Watch, Box, Papers | 2023 | 37.3mm

Rolex Day-Date 40 228235

$51,750.00
Watch, Box, Papers | 2022 | 40mm

Rolex Day-Date 40 228238

$51,495.00
Watch, Box, Papers | 2024 | 40mm

Patek Philippe Golden Ellipse 3545/2

$22,255.00
Watch, Box, Papers | 1972 | 32mm

Vintage

Rolex Datejust 36 16200

$4,660.00
Watch Only | 2000 | 36mm

Rolex Datejust 41 126334

$13,975.00
Watch, Box, Papers | 2024 | 41mm

Vacheron Constantin Historiques Chronograph 47111/000J

$38,295.00
Watch Only | 37mm

Girard-Perregaux Collection Prestige Vintage 1945

$25,875.00
Watch, Box, Papers | 2001 | 32mm

Breguet Classique Perpetual Calendar 5327ba/1e/9v6

$31,050.00
Watch Only | 39mm

Breguet Classique 5140BA/12/9W6

$15,270.00
Watch, Box, Papers | 40mm

Vintage

Rolex Lady-Datejust 69174

$5,435.00
Watch Only | 1987 | 26mm

Rolex Datejust 41 126334

$21,735.00
Watch, Box, Papers | 2026 | 41mm

Mens Dress Watches

Men’s dress watches are the ultimate expression of timeless elegance and refined craftsmanship. Designed to complement formal attire, these watches typically feature slim cases, minimalist dials and classic leather straps or sleek metal bracelets. Brands like Patek Philippe, Jaeger-LeCoultre, Vacheron Constantin and Cartier have been leaders in this category for decades, emphasizing precision and understated sophistication. Originating in the early 20th century, dress watches were created to offer a clean, elegant look without sacrificing mechanical excellence. The focus is on quality movements and lasting appeal, with many models showcasing hand-finished details and precious metals. Their simple yet polished designs make them perfect for business, black-tie events or any occasion where subtlety meets style.

Womens Dress Watches

Dress watches for women represent the perfect blend of style and horological craftsmanship. Designed to be both beautiful and functional, these watches usually feature slender cases, elegant dials and high-quality materials. Many models incorporate subtle decorative elements such as diamond accents or mother-of-pearl faces to enhance their feminine appeal. Historically, these watches have been cherished for combining mechanical precision with delicate aesthetics. Renowned names like Cartier, Jaeger-LeCoultre and Rolex are celebrated for their expertise in creating timeless dress watches that offer lasting style and expert finishing. These watches focus on simplicity and sophistication, with clear markers and understated designs that complement formal and professional attire. Women’s dress watches remain essential for anyone seeking refined elegance and dependable performance in their wristwear.