In this, the second of two posts, Ivy-Style looks at clients of legendary clothier Chipp, as recounted by Paul Winston in our recent interview with him. For this one, on IBM president Thomas J. Watson, Jr., contributing writer Chris Hogan takes the reins.

Although Fortune magazine proclaimed him the most successful capitalist in history, Thomas Watson, Jr. was no pinstriped egomaniac. In fact, the IBM president was quite the opposite: a consummate gentleman who once said, “Really big people are, above everything else, courteous, considerate and generous — not just to some people in some circumstances — but to everyone all the time.”

Born in Short Hills, NJ, Watson prepped at the Hun School of Princeton and then went on to Brown University. Never a great student, “Terrible Tommy” usually put drinking and dancing ahead of studies.

But he soon became the kind of leader you wanted to follow. In 1952 he was appointed president of the company his father founded, and spent the next 19 years building IBM into the unchallenged giant of the computer industry, and one of the largest corporations in the world. Forward thinking and adaptive, Watson embraced mainframe computers and moved IBM from punch cards to electrons.

Although he was very much a modern leader, it was Watson who formalized the now legendary conservative IBM uniform of gray suit, white shirt and “sincere” tie. Former IBM employee and computer industry pioneer Bob Bemer recalled that he was once scheduled to appear on a TV program in the ’50s. Apparently white shirts were blinding on early TV cameras, and Bemer had to get special permission from IBM management to wear a blue shirt.

When Watson retired from IBM in 1971, he traded in his suit and tie for a captain’s hat and spent considerable time on the water. He won awards from the New York Yacht Club and the Cruising Club of America for guiding his sailboat farther up the coast of Greenland than any non-military ship had ever ventured. Watson also followed Captain Cook’s route across the Pacific and, in appropriately noteworthy fashion, named seven successive sailboats Palawan.

In 1979 President Carter appointed Watson ambassador to the Soviet Union.

Watson also had a love of flying, and in 1986 was the first private citizen granted permission from then Soviet Premier Mikhail Gorbachev to pilot his jet across all the time zones of the Soviet Union. — CHRIS HOGAN