If fashion is about flash then Will Vicars might have looked an outside bet. The chief investment officer and part owner of Caledonia Investments manages billions on behalf of some of the country’s richest and most private families, and Vicars tends to be just as private. He keeps well below the radar, successfully avoiding the Financial Review Rich List until he popped up in 164th spot for the first time this year (those close to him speculate his wealth is much higher than the estimated $527 million). His clothes look expensive, but you won’t get far making small talk about what labels he likes to wear.

Yet here Vicars is, on a sparkling Friday afternoon in June on Sydney Harbour, watching as a glamorous Hungarian model (day rate $40,000) poses in sewn-together silk scarves on the teak deck of his yacht, the 78-foot Drumfire, for a photographer, a battalion of make-up artists, hairdressers and stylists standing by. It’s all in aid of creating the perfect image for Oroton, the 80-year-old Australian luxury leathergoods and accessories retailer. “We’re putting serious money into this,” says Vicars.