She has the distinction of submitting the highest expenses claim in the history of Condé Nast - for a dilapidated building. Issie wrote on the expenses form, 'Just £50,000 for a very small ruin that really was a must'. It went unpaid.
Issie immediately created a stir by the bold outfits she turned up to work in, and her eccentric manner. Wintour recalls, 'People would stop by my office just to see what Issie was wearing that day. One morning she might be in full punk regalia, the next dressed like a maharajah, dripping in jewels and sari silks.'
It rapidly became clear that although Issie was not a great administrator, she was highly creative, and hard-working - on things that interested her, at least - and second-to-none at spotting new talent. Wintour says, 'Every day she'd leave Vogue as if her working day was only beginning; the next day she'd come in and relate with breathy excitement about the new artist, the new designer, the new photographer, the fabulous girl we absolutely must work with.'
As Wintour observed, 'the more something shocked her, the more it captivated her imagination'. One such discovery was the painter, Jean-Michel Basquiat, Andy Warhol's collaborator. Both Warhol and Basquiat ended up doing assignments for Vogue as a result of Issie's introductions. Issie met Warhol at a party where she was wearing one silver and one purple shoe of the same style by Manolo Blahnik. Warhol came up to Issie and said, 'Gee, you had to buy two pairs of shoes to get that look.' Their friendship was to last until his death in 1987.