Fashion mavericks from Anna Piaggi to Isabella Blow weren't afraid to rip up the rule book

Sometimes greed is good. I'm not talking avariciousness or materialism, but that hunger to see more, do more, be more, that pushes people forward. Whether that is the pursuit of truth, beauty, or the perfect shade of red. It's this desire that drives fashion's larger -than-life characters.

Diana Vreeland, Isabella Blow, Iris Apfel are all women who forged a unique path stylistically, and challenged the status quo. They were never in hock to individual designers. Their style is unapologetic: it might look garish to some or vulgar to others, but they would not care a jot. This spirit of liberation and proud individualism resonates this season. What could be more modern than that?

It's been a long time since Gucci could be called modern. But this season something surprising has happened: all of a sudden Gucci is the talk of the town thanks to the appointment of a new creative director. Not since Tom Ford's Nineties heyday has the brand been so discussed, coveted and copied.

In January, Alessandro Michele, himself a protégé of Ford but with a distinctly different aesthetic, was plucked from obscurity – he was head of accessories at the time. Less than a month later, he presented his first womenswear collection: a romantic paean to extreme eccentricity, a stark contrast to the house's long-running "sex sells" template, which had fallen distinctly out of fashion when it comes to the modern woman's wardrobe.

Despite the current fetish for physical fitness that's obsessing many in the West, there is now a greater acknowledgement that women ought to be praised for what's inside rather than outside the body beautiful. That's not to say that brands peddling high-octane glamour and super-sexualised shapes have been consigned to the bargain bin. They still sell, but they are not the brands setting the agenda. Mark that down to fashion's contrariness if you will.

Iris Apfel, the nonagenarian star of the recent documentary Iris – which I implore every one of you to watch – is a truly inspirational figure. Her eclectic style and exotic beauty have earned her the nickname "the rare bird of fashion". Although Apfel's passion for clothes and costume jewellery stretches back to her youth, it is only in the last decade that her role as style icon has gone mainstream. Quick-witted yet kind, Apfel's mind is still sharp. But it is for her fashion nous that she has won plaudits in recent years: the way she piles on costume jewelleryfor instance. She holds no truck with Coco Chanel's mantra to take one thing off before leaving the house.

Apfel is one of an endangered species that included Diana Vreeland, Anna Piaggi, Isabella Blow – eccentric creatures who lived for fashion and beautiful things. None of them were afraid to take risks and make mistakes, to offend or look vulgar – better that than being boring or bland. Their spirit of rebellion lingers and what a blessed relief that it does – it empowers women to fight against convention, expectations and typecasting.

In our hearts we know that Apfel and her kind's unapologetic style is unique and inimitable, but who can blame us for being inspired by that self-confidence and joie de vivre.

It's no coincidence that this celebration of the oddball comes at a time when the unreality of social media is gathering strength. It's no longer just the glossy pages of a magazine that ooze polished perfection; now everything looks rosy thanks to Instagram filters and Photoshop.

There is a refreshing sense of messiness to Michele's Gucci that reflects reality in a way that most luxury labels of that calibre would fear. Yes, everything was luxurious and crafted from the finest fabrics, but there was none of the coldness of his predecessor's perfect polish. Instead there was a sense that his women were living, breathing characters. That they'd been whisked from wherever they happened to be and would duly go back and carry on long after the designer had taken his bow.

Michele isn't the only one taking unsubtle sexiness off the table. In Florence in June, the first collection for Pucci by Massimo Giorgetti was a thoroughly modern affair, with "ageless" the byword. And while it's true that canary-yellow feathers are tricky to pull off at any age – it's something that perhaps would only be attempted by the most confident of dressers – it's a fine thing not to be concerned with the futile objective of looking beautiful or perfect.

There's been a childish mood brewing in fashion of late. Children dress without understanding the arbitrary rules of what supposedly goes with what. The best-dressed women know the rules, they just don't care about breaking them. And what could be more empowering? Women of the world take heart. This season, fashion favours the bold.