In the latest decision the Milan provincial tax commission rejected an appeal by the designers and ruled in favour of Italy's tax authority, Agenzia delle Entrate.
In its findings, the commission found "conduct of abuse with the only goal of obtaining a fiscal advantage".
Investigators claimed the price at which the companies were sold – 360 million euros – to the holding company was about one third of their true market value.
The designers have always denied the allegations and said the charges were based on "a completely abstract calculation" of their companies' value.
Apart from the massive fine, the business partners face prison sentences of up to five years if found guilty. It is unclear whether the fashion designers will take the latest decision to the next level of appeal.
The case attracted a great deal of interest in Italy since technocrat government of prime minister Mario Monti adopted a hardline on tax avoidance last hear. Finance police and tax inspectors conducted a number of high-profile raids across the country in a bid to clamp down on a black economy estimated to account for 17 percent of Italy's gross domestic product.
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