A 60th deserves more than another sweater. It is a milestone worth marking with something he will keep, or a day he will tell stories about.
My favorite idea on this list is a watch made in the year he was born. The rest are built to last another sixty years, or to be remembered just as long.
Diana Ostroff, Founder
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For the 50th or 60th: a vintage Rolex, Omega or Patek made in his birth year, from Chrono24's verified dealers. Ask the dealer for the watch's papers to confirm the year.
The 153rd Run for the Roses, from the fourth floor: indoor dining and a covered terrace overlooking the finish line. The first Saturday in May.
Saturday and Sunday at the most glamorous race of the year, from a lounge overlooking the first corner: champagne reception, open bar, gourmet menu and live entertainment. June 2027.
A chronometer-certified steel dive watch, rated to 300 meters. Mark the 50th or 60th with a watch he'll wear for the next twenty years.
Keeps two automatic watches wound and ready, with a drawer below for the rest of his collection. The natural companion to a birthday watch.
The greatest moments, courses and players in golf, hand-bound in a clamshell case and written by George Peper, former editor of Golf magazine.
Montblanc's flagship pen with an 18K gold nib. For signing the deals he's known for.
Heavy French crystal in Baccarat's oldest pattern. The bar cart's centerpiece for decades.
A private four-course pairing with select Opus One vintages and an in-depth winery tour in Napa. For 4 to 8 guests; book 14 days ahead.
A 90-minute session on a real handling circuit with a professional coach, from a Boxster up to a 911 GT3.
Six hours in Chicago assembling his own mechanical watch, then he takes it home with his initials engraved inside. A rare gift for a collector who has bought everything else.
A year of 160 lab tests drawn at Quest, with results and trends in one app. For the man who tracks everything but his own biomarkers.
A cover that cools or warms each side of the bed separately and tracks his heart rate and sleep without a wearable. Requires a yearly membership from $199.
The compression boots elite athletes use after training. Air pulses up each leg in waves to move circulation after golf, tennis or a long flight. Most models are FSA/HSA eligible.