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.

169 products

Rolex Day-Date 40 228238

$64,170.00
Watch, Box, Papers | 2024 | 40mm

Rolex Datejust 41 126333

$19,150.00
Watch, Box, Papers | 2025 | 41mm

Vintage

Rolex Oyster Perpetual Date 15203

$6,730.00
Watch, Box, Papers | 1993 | 34mm

Rolex Datejust CPO 41 126334

$13,455.00
Watch, Box, Papers | 2019 | 41mm

Cartier Tank A Guichets WGTA0234

$122,130.00
Watch, Box, Papers | 2026 | 37.6mm

Vintage

Rolex Datejust 36 16013

$6,210.00
Watch Only | 36mm

Jaeger-LeCoultre Ultra Thin Master 174.8.90.S

$6,210.00
Watch Only | 40mm

Vintage

Rolex Oyster Perpetual 34 6564

$7,765.00
Watch Only | 1958 | 34mm

Rolex Datejust 41 126300

$11,385.00
Watch, Box, Papers | 2021 | 41mm

HYT H0 Liquid H00840

$17,595.00
Watch, Box, Papers | 48.8mm

Tudor Royal M28600-0001

$3,315.00
Watch, Box, Papers | 2025 | 41mm

Rolex Oyster Perpetual 134300

$12,940.00
Watch, Box, Papers | 2025 | 41mm

Cartier Santos De Cartier WSSA0062

$9,215.00
Watch, Box, Papers | 2025 | 40mm

MB&F Time To Love M.A.D.1

$5,955.00
Watch, Box, Papers | 2024 | 42mm

IWC Chronograph Portuguese IW371480

$11,905.00
Watch Only | 41mm

Vacheron Constantin Quai De L'ile 4500S/000A-B196

$17,080.00
Watch & Papers | 2018 | 41mm

Cartier Tank Americaine W2609156

$10,195.00
Watch, Box, Papers | 2011 | 27mm

Cartier Santos De Cartier WSSA0029

$8,230.00
Watch, Box, Papers | 2026 | 35mm

Vintage

Rolex Datejust 36 1603

$9,835.00
Watch Only | 36mm

Cartier Santos De Cartier WSSA0029

$7,245.00
Watch, Box, Papers | 2022 | 35mm

Jaeger-LeCoultre Master Geographic 142.8.92

$6,730.00
Watch Only | 38mm

Patek Philippe Nautilus 7010G-013

$77,625.00
Watch, Box, Papers | 2026 | 32mm

Jacob & Co. Astronomia Solar Planets AS300.40.AP.AK.AFL4A

$253,575.00
Watch, Box, Papers | 45mm

Jaeger-LeCoultre Geophysic 8008520

$9,830.00
Watch, Box, Papers | 2015 | 39mm

Rolex Datejust 31 278274

$13,975.00
Watch, Box, Papers | 2026 | 31mm

Rolex Datejust II 116333

$13,455.00
Watch Only | 41mm

Jaeger-LeCoultre Master Control Chronograph Calendar Q4138420

$17,080.00
Watch, Box, Papers | 2020 | 40mm

Jaeger-LeCoultre Reverso Classic Large Small Seconds Q3858520

$9,725.00
Watch, Box, Papers | 2022 | 46mm

Rolex Oyster Perpetual 124200

$11,385.00
Watch, Box, Papers | 2026 | 34mm

Vintage

Rolex Datejust 36 16030

$4,660.00
Watch Only | 1985 | 36mm

Rolex Datejust 36 126234

$14,490.00
Watch, Box, Papers | 2026 | 36mm

Rolex Oyster Perpetual 126000

$10,350.00
Watch, Box, Papers | 2026 | 36mm

Rolex 1908 52506

$46,575.00
Watch, Box, Papers | 2026 | 39mm

A. Lange & Söhne Lange 1 Perpetual Calendar 345.036

$139,725.00
Watch, Box, Papers | 2026 | 42mm

Rolex Day-Date 40 228235

$49,680.00
Watch, Box, Papers | 2022 | 40mm

Vintage

Rolex Date 15233

$6,210.00
Watch Only | 1990 | 34mm

Vintage

Rolex Datejust 36 16013

$4,140.00
Watch Only | 36mm

Rolex Datejust II 116334

$9,835.00
Watch Only | 41mm

Vintage

Rolex Datejust 36 16234

$8,280.00
Watch Only | 1999 | 36mm

Jaeger-LeCoultre Reverso Tribute Duoface Calendar Q3918420

$17,080.00
Watch, Box, Papers | 2025 | 49mm

Glashütte Original Panomaticlunar 1-90-02-43-32-05

$8,800.00
Watch, Box, Papers | 2018 | 40mm

Rolex Datejust 41 126300

$10,040.00
Watch, Box, Papers | 2024 | 41mm

Cartier Santos WSSA0061

$7,455.00
Watch, Box, Papers | 2023 | 35mm

Grand Seiko Elegance SBGW259

$6,730.00
Watch, Box, Papers | 2024 | 38mm

Cartier Tank Must Black Cartier WSTA0072

$4,195.00
Watch, Box, Papers | 2022 | 34mm

Ulysse Nardin San Marco Alarm 603-77

$3,105.00
Watch Only | 38mm

IWC Chronograph Portuguese IW371480

$11,905.00
Watch Only | 41mm

H.Moser & Cie. Pioneer Centre Seconds 3200-0903

Price on Request
Watch, Box, Papers | 2019 | 42.8mm

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.