Street style. The term conjures endless images of white, middle-class dandies with too much time and money on their hands, boasting their style credentials from one high street coffee chain to another, itching to run into Scott Schuman from The Sartorialist so they can light a cigarette in an enigmatic and seductive manner.

And yet street style is about much more than creatively starved art students who’ve clearly spent hours in front of the mirror practising the obligatory pretentious ‘Street Style Pose’, which usually entails standing on one leg like a contrived flamingo and avoiding looking into the camera so as to create a sense of ‘sprezzatura‘.

Rather, as I hope to illustrate throughout this post, street style is an essential force that drives both the high fashion industry and high street trends. More importantly, when done correctly, it can be an art form in itself – reflecting the complex relationship between the world of aesthetics and the real world.

If you’re still not convinced, perhaps you’ll feel differently after I share some of my favourite street style images of all time with you…

Street Style: The Humanitarian Aspect

Florence Street Style Image

Florence Street Style (Above Left)

This first image is of a very dashing young man wearing a beautiful camel overcoat in Florence. What always excites me about this photo is the sense of movement it evokes.

There’s nothing contrived here. This is a genuine snapshot of a human being living their everyday life and showcasing the role that style has to play in that life.

This guy is not ‘stylish’ because of the clothes he wears – it’s the way he stands, the way he moves and, in my imagination at least, the way he lives.

Italian Street Style (Above Right)

If anyone is ever lost as to why I romanticise the Italians as such a magical people, I show them this photo.

There is so much humanity in this image, that I often don’t see the clothes. The only thing more tangible than the union that their style lends them is the obvious friendship between these two men.

Street Style: Transcending Generations

Street Style Can Inspire Current Trends and Looks

Twentieth Century Street Style (Above Left)

Ah, now we come to my favourite. This photo was taken in North Africa at the beginning of the twentieth century.

What I adore about this image is the way it symbolises the interaction between timeless style and current trends. The tie pin and sartorial excellence of the top half contrast with the very modern lack of break of the trouser legs.

In reality, this dapper chap probably just didn’t have any other trousers that fit him better, but the exposed socks and immaculate footwear look so contemporary that you can see why designers might be inspired by such an iconic image.

Twenty-First Century Comparison (Above Right)

We can see how enduring street style images are through comparisons with more recent examples. I’ve already mentioned the notable lack of break in the trouser leg, but how can a seemingly trivial detail like this transcend changes over time and crop up in a photograph taken in the early twenty-first century? Well, it seems they have done just that.

The same details still jump out at us: there’s the beautifully trim silhouette, created by some expertly slimmed down tailoring, and a very fashion-forward cut. Yet at the same time, we are still struck by the gentleman’s choice to hem his trousers so that they have very little break.

It’s executed with a little more forethought, granted, but the visual impact is the same.

Street Style: A Cultural Snap-Shot

Rockers On Chelsea Bridge & Alex Turner's Inspired By Look

Taking a more historic approach to street style can yield some surprising conclusions, especially when applied to widespread cultural trends like that of the Mods and Rockers.

Take the image above (top left), for example, this striking photo of three Rockers on the Chelsea Bridge actually reflects an important transition between the ‘Teddy Boy’ style of the 1950s and the more contemporary rock-influenced styles that we see all around us today. Iconic modern performers like Alex Turner from the Arctic Monkeys (above right) have clearly been inspired by an amalgamation of all of these teen subcultures.

However, it is also much more than just a snapshot of a cultural fad. The clothes that the Mods and Rockers chose to wear weren’t just indicators of rebellious progressivism or musical tribalism. They reflected important frictions arising between the status quo and the nation’s youth.

This association exists today. The leather jacket. The Pompadour. Distressed denim. As every iconic rock front man knows, these are all weapons in the timeless arsenal of the nonconformist. Morrissey’s James Dean-inspired quiff was the glue that held together the more eccentric aspects of his musical persona, just as Sid Vicious became a hero to thousands of disillusioned youths without ever seemingly playing a correct musical note.

Even today, when I slip into a pair of skinny jeans or when I don my beloved denim jacket, I am making a social, cultural and historical statement. I may not know it at the time – I may just think I look damn good – but on a deeper level, what we all choose to wear is inseparable from how we wish to align ourselves with conformist society. And where is the ideal battleground to make such statements?

The street, of course. And this, above all the other reasons I have mentioned in this article,
is why street style really matters.

Final Word

As you can see, street style is much more than a means to an end for art school drop outs and aspiring fashion photographers. It’s a glimpse into the complex relationship between fashion and history, heritage and humanity.

Please feel free to share links to your favourite street images of all time in the comments section below and tell us all why you love them so much…