From the INSEAD case study:

"Starting in 1991, Maurizio Marchiori, the newly-appointed advertising director, developed a global branding campaign in-house with the help of Paradiset, a Swedish advertising agency. The campaign appropriated the “products make better living” theme popular among advertisers in the 50s and turned it on its head in the “Diesel for Successful Living” campaign. Diesel’s vision of consumer paradise was to be interpreted ironically; the standard promise of “success” was exaggerated, made absurd, even mocked. Serious themes seemed to be lurking everywhere in the adverts but were undercut by a final admission that it was all just a joke."

Well there you go. I have difficulties imagining an American brand to fool around with the American dream like that.

seems also to be influenced by the northern European raggare and Italian paninaro scenes in the early/mid 80s.
The more retro the look and styling the better it sold.

The Chevignon sweats , dungarees and chucks look in particular ,
I think I would have seen that combination first in Ibiza about 89/90 as it seemed to be the uniform of the 'international tourist thieves' selling drugs around the beach bars.

oh Iceberg, how very Rimini 92.