Underwood Jewelers

Underwood Jewelers is a jewelry and watch store in the San Marco neighborhood of Jacksonville, and by a wide margin the most established shop in this list — the business has operated continuously since 1928 and is now run by its sixth generation of family ownership. Underwood's holds official dealer status for Rolex, and its offering extends into designer jewelry, engagement rings, and other luxury watch brands including Tudor. The shop is also a member of the American Gem Society, an industry body whose membership is limited to jewelers meeting specific ethical and educational standards — a credential the shop points to directly as part of how it presents itself to customers. The business runs a recurring promotional program, introducing a new limited-quantity jewelry special each month across a range of styles and price points, and features both engagement and fashion designers as part of its ongoing collection. Beyond sales, Underwood's serves Jacksonville, Ponte Vedra Beach and the wider northeast Florida area, with a long-term-quality philosophy that has evidently kept the business in the same family for nearly a century — a rare thread of continuity for a jewelry store of any size, let alone one holding an official Rolex dealership.