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.

67 of 161 products

Rolex Sky-Dweller 326935

$42,955.00
Watch, Box, Papers | 2019 | 42mm

Rolex Datejust 36 116233

$11,385.00
Watch & Papers | 2009 | 36mm

Rolex Datejust 41 126300

$10,350.00
Watch, Box, Papers | 2024 | 41mm

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 41 126334

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

Vintage

Rolex Datejust 36 16013

$6,210.00
Watch Only | 36mm

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

Rolex Oyster Perpetual 134300

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

Vintage

Rolex Datejust 36 1603

$9,835.00
Watch Only | 36mm

Rolex Datejust II 116333

$13,455.00
Watch Only | 41mm

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

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

Rolex Datejust 41 126300

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

Vintage

Rolex Day-Date 36 18038

$64,690.00
Watch, Box, Papers | 36mm

Rolex Oyster Perpetual 134300

$10,870.00
Watch, Box, Papers | 2026 | 41mm

Rolex Perpetual 1908 52508

$26,395.00
Watch, Box, Papers | 2024 | 39mm

Rolex Day-Date 40 228238

$50,715.00
Watch, Box, Papers | 2022 | 40mm

Rolex Datejust 31 78240

$8,800.00
Watch Only | 31mm

Rolex Lady-Datejust 279174

$10,350.00
Watch, Box, Papers | 2017 | 28mm

Rolex Datejust 31 278274

$12,940.00
Watch, Box, Papers | 2022 | 31mm

Rolex Datejust 36 126234

$12,940.00
Watch, Box, Papers | 2022 | 36mm

Vintage

Rolex Datejust 36 16203

$7,765.00
Watch Only | 36mm

Rolex Datejust 31 278274

$14,235.00
Watch, Box, Papers | 2026 | 31mm

Rolex Datejust 36 126231

$21,220.00
Watch, Box, Papers | 2022 | 36mm

Rolex Sky-Dweller 326934

$24,840.00
Watch, Box, Papers | 2022 | 42mm

Rolex Lady-Datejust 179174

$5,900.00
Watch & Box | 2009 | 26mm

Rolex Oyster Perpetual 41 134300

$11,180.00
Watch, Box, Papers | 2025 | 41mm

Rolex Oyster Perpetual 124300

$9,525.00
Watch, Box, Papers | 2025 | 41mm

Rolex Day-Date 40 228238

$58,995.00
Watch, Box, Papers | 2026 | 40mm

Rolex Datejust 126200

$11,385.00
Watch, Box, Papers | 2026 | 36mm

Vintage

Rolex Datejust Turn-O-Graph 16263

$6,730.00
Watch & Box | 1991 | 36mm

Rolex Datejust 116234

$7,765.00
Watch Only | 36mm

Rolex Datejust 41 126334

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

Rolex Datejust 41 126300

$10,870.00
Watch, Box, Papers | 2022 | 41mm

Rolex Day-Date 18038

$9,315.00
Watch Only | 1987 | 36mm

Rolex Datejust 41 126334

$15,525.00
Watch, Box, Papers | 2023 | 41mm

Rolex Day-Date 36 118135

$20,700.00
Watch & Box | 36mm

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.