Generation style: style icons through time

Physically, we have many tools to gauge something: thermometers, rulers, and beakers are just a few. Socially, we have less. In fact, to gauge the inner minds of those whose company we are gracing, there is a rather reliable social gauge that we often find ourselves turning to in times of faltering conversation: the dinner party. If you could have a dinner party with any three people, dead or alive, who would you pick?

It is a question of limited success, with an equal capacity for ice making as it does ice breaking, and yet when asked, it has all the potential to highlight the shadowy sides of someone’s subconscious. From someone’s wider interests to their deeply held values, who is chosen for one of the coveted three seats is a social gauge of who exactly a person is. And in fashion circles, there is the possibility that a style icon, or three, might be chosen. After all, if we’re throwing a dinner party, should we invite Bella Hadid?

However, despite ‘icon’ implying the almost-universal appraisal of an individual, who counts as an icon, especially a style icon, can mean many things. Is it someone who is unashamedly bold and daring in their fashion choices, and if so, what counts as bold and daring? How do these categories of judgement change over time? Is a style icon simply someone who is recognised for having style, and if so, shouldn’t some of us count as style icons?

Monroe immortalised Hollywood, lacing glamour and elegance with threads of easy Americana, leaving behind a legacy that defined an era

While there is no easy answer to these questions, and quite frankly they move too easily from talk of the fashionable to the philosophical, when talking about a style icon, it becomes clear that each generation has offered an individual, or two, to rank in our collective consciences as those illusive ‘style icons’.

Starting in the spotlight of Hollywood’s Golden Age, the 1950s gifted us with many a silver screen starlet. But none were as starry as Marilyn Monroe. With classic blonde curls and a smirking red lip, Monroe emerged as the Hollywood pin-up – equal parts sultry as she was stylish – with an innate ability to enrapture audiences. While her charisma created an all-consuming aura of confidence, it was her style choices that elevated her to icon status.

From the white dress she wore in Billy Wilder’s The Seven Year Itch, to the offscreen capri pants and crisp white shirts, Monroe immortalised Hollywood, lacing glamour and elegance with threads of easy Americana, leaving behind a legacy that defined an era.

But, if the 1950s were Hollywood, then the 1960s were Hampstead Heath. With the British Invasion swinging the cultural conversation onto all things Brit, it only makes sense that our 1960s icon is Twiggy: arguably the world’s first supermodel, and a key player in the Mod era. Pushing past the petticoats of the skirts of previous decades, Twiggy embraced the Mary Quant mini, embodying the sexually liberated ‘Single Girl’ that had emerged from the sexual revolution. Patterned tights, pixie cuts, and playful eye makeup, Twiggy’s experimentation pushed the boundaries of fashion, tearing open a portal of possibility within the fashion world, and ensuring that she had left a rather stylish mark.

Embracing such possibility, yet revamping it for the 1970s, was the socialite and humanitarian, Bianca Jagger. A true trailblazer, Bianca Jagger was a pioneer in power-dressing, with double-breasted blazers, wide-legged trousers, and classic-cut coats all forming part of her essential wardrobe. Combining both the sophistication of the 1950s and the sexually liberated 1960s, Bianca Jagger knew what it meant to be a modern woman. And this is no clearer than in that image, where she is stood next to her husband, Mick Jagger (a style icon in his own right), on their wedding day, wearing an Yves Saint Laurent bridal suit and actively redirecting the trajectory of ‘coolness.’

This trajectory unfortunately strayed off course for most of the 1980s. Despite this, the style icon defining this generation, the material girl herself, Madonna, remains revered for her impact on fashion and pop culture, with Karl Lagerfeld naming her as the “single greatest fashion influence in the world”. From her risqué white lace wedding dress for Like a Virgin to the corseted femme fatale Jean Paul Gaultier created for her 1990 Blond Ambition World Tour, Madonna was the queen of reinvention, using her prowess as a performer to breathe life into her bold choices. Being able to mix latex and tutus, and embrace every fluorescent colour of the rainbow, is not an easy feat, and to make it fashionable enough for Vogue to recognise – Madonna was the first musician to grace the cover in 1989 – is another thing entirely. The 1980s may have sidestepped style (in the strictly traditional sense), but Madonna was undoubtedly stylish.

Now, having danced through some decades, flitting through the wardrobes and style files of actresses, models, socialites, and musicians, for the 1990s, we step into the streets of New York and onto the television set of the iconic Sex and the City, with it’s equally iconic, if a little problematic, main character, Carrie Bradshaw. Pairing $7 vintage slip dresses with her $300 mismatched Manolo Blahnik’s, Bradshaw’s chaotic-chic style, as created by costume designer Patricia Field, both prophesied and summarised the nineties, speaking to its minimalist overtones and grungey undertones. By strutting along the fine line between style success and fashion failure, Bradshaw’s eclecticism embodied what it means to be a fashion icon: embracing the bold while consistently being ahead of the trend curve.

For now, when discussing ‘style icons’, looking back at the offerings from previous generations can be all the more rewarding

This becomes more evident when we turn our attention to Y2K trends. With Bradshaw sporting crop tops and decorative belts before the millennium, her nineties know-how helped ease fashion into the new decade. Without icons like Destiny’s Child infusing their much-needed star quality into the 2000s trends, we may never have seen the current resurgence in Y2K at all. From their scandalously low-waisted jeans and coordinated girl-group glittery bandeau tops, to their khaki cargos and embellished denim, the quintessential R&B and pop group defined 2000s style, leaving them with the status of true style icons. After all, elevating double denim requires a certain deftness with designs.

As for who would count as our style icons for the 2010s and 2020s? Well, I’d say that is still up for debate. We could have Alexa Chung, Rihanna, Zendaya, or Kim Kardashian; the list is endless. And with these ‘icons’ still actively vying for that status, who is to say that they’re icons only of that era? As we see resurgences of the best trends of those decades, we may be able to say who created the best looks of their time. For now, when discussing ‘style icons’, looking back at the offerings from previous generations can be all the more rewarding.

So, if you find yourself asked about dinner parties and you’re scrambling to think of the invitees, flick through the style files from archives past – there might be a style icon or two that could make the guest list.