A family death notice said Sir Clifford died peacefully on Thursday. He was 94.
Sir Clifford was the founder of the Skeggs Group, whose investments over the years has included seafood, tourism, wine, property and for a short stint, aviation.
He was elected to the Otago Harbour Board in 1968 and, five years later, was made chairman.
In 1971, he was elected as a Dunedin city councillor and was eventually elected as mayor for four terms between 1977 and 1989.
Dunedin businessman Allan Dippie said Sir Clifford was a mentor.
"[He] encouraged me in business and I learnt a lot from him. We did a bit of business together, he was a pretty tough rooster to deal with at times, but if you took a firm position back, I always thought that he respected that."
Mr Dippie first met Sir Clifford where he was a "young primary schoolboy" and on a class trip to Port Chalmers.
"I thought he was fantastic and even at that young age he made quite an impression."
When Sir Clifford later became the mayor, Mr Dippie said he "was a true champion of getting things done".
"He told me once that the large majority of his councillors always agreed with his decisions, and he never put anything to the vote unless he knew the outcome. That’s why the right things got done under his leadership."
In 2002, Mr Dippie’s company bought land in Wānaka from the Skeggs Group that is now Three Parks,
a project Sir Clifford "always took a keen interest in".
"Sir Cliff Skeggs Dr is a road I was pleased to name after him ... although he never said it, I think he was quietly pleased about it."
Dunedin Mayor Jules Radich said he would hold his memories of Sir Clifford "dear".
"Sir Clifford was a significant figure in our community — I had the pleasure of meeting [him] on several occasions and always found him to be a particularly positive and dynamic person, and I had the pleasure of hearing several of his fascinating stories of things he had done.
"His was a remarkable life of achievement and dedication, and one worthy of recognition, as evidenced by the knighthood he received."
Sir Clifford was a "pioneering businessman" and found many ways to contribute to the South Island community, he said.
Originally from Bluff, Sir Clifford eventually left Southland and headed to Port Chalmers to begin a five-year boat-building apprenticeship with Miller and Tunnage in 1947 at age 16.
Aged 22, he employed four boat-builders with whom he had served his apprenticeship.
Investing the $240 he had saved, he started a business converting fishing boats for crayfishing.
Sir Clifford was knighted in 1987 during his mayoralty.
He is survived by his wife Marie, Lady Skeggs, his sons and daughter-in-laws and his grand and great-grandchildren.
At Sir Clifford’s request a private family farewell will be held.
His third son, Graeme, died last year.
