Last month, as I walked along Oxford Street, I caught the unmistakable and quite extraordinary energy of a city that has turned its pavements into catwalks. I mean, look, for instance, at the truly contemporary styles that have emerged recently. They are a gentle mix of the virtually effortless urban ensemble and the sharp silhouettes of today—a blend that still manages a well-tailored appearance.
It’s really about what is possible with everyday clothing, with some balance between the oversized hoodie and the apparently distressed denim; it’s about some clear thinking as to the fresh appearance of streetwear that does—at last—kind of reflect its name. I spotted an eye-catching look that encapsulates this new direction. A young man strolled past me in an outfit that was, for lack of a better term, tailored streetwear.
It was the kind of look that might have been a little too dressed-up for daytime (unless you were going to a pretty fancy daytime event), yet it worked because the pieces were styled with a casual, unstudied air. He wore a blazer that wasn’t too big or too small, over a crew-neck pullover (that, for all I could tell, could have been some kind of fancy sweatshirt), and trousers that tapered just enough to show off his sneakers. Again, it wasn’t one for the ages, but the combination was striking enough that I found myself staring at him as he passed.
How I dress for the city has changed. Rigidly following one ‘look’ dictated by high-end runways is a thing of the past. Now, it’s about outfits that feel both spontaneous and thoughtfully curated.
Embracing my collision of styles has taken me to a blend of well-tailored basics that make the nod to vintage something I feel comfortable doing. The garments I wear have stories to tell. And that kind of authenticity is what I see in my fellow commuters when I spot them en route to something they feel even more comfortable doing: taking creative risks with their personal style.
In practical terms, mastering the urban aesthetic means investing in pieces that can see you from day to night, from right here to right there. And that means you ought to consider a well-fitted blazer. It’s not just for boardroom meetings anymore; it can easily elevate a pair of jeans or balance the informalities of graphic tees.
These are popping up everywhere, from the streets of Manchester to the working-class corners of Soho, and are worn with an ease that belies their somewhat stuffy reputation. When paired with smart sneakers or even well-thought-out boots, they send the same message as the weekday looks we’ve outlined: sophistication doesn’t mean you have to be uncomfortable or over-polished. Today, street style is more than just a visual statement.
It’s deeply interwoven with the practicality we all crave as urban dwellers. We have to contend with so many variables when it comes to dressing. Prêt-à-porter just doesn’t cut it for all of us, for all occasions.
Beauty and brains do exist in some well-crafted street style. I pursue both, searching for pieces that make sense no matter how many different ways you might attempt to layer them. And in the base stuff of my wardrobe, from which I intend to work outward, I want specified resilience both for the pieces themselves and the looks I can conjure with them.
In the last few weeks, I have seen a trend among influencers and nearby fashion bloggers that I appreciate: They have taken to Instagram to embrace what I—and, I suspect, many of you out there—consider a classic street style. This isn’t just about taking pictures in front of graffiti murals or in the entrances of the latest restaurants, though; it’s about finding an aesthetic that works in the ever-changing setting of the city. And I would say that the piece that really captured this “trend” (if we can call it that) was, in my view, an Instagram post of an outfit just thrown together to go about one’s day.
This developing trend isn’t limited to one group; it’s a diverse blend of influences. You have college students who are nailed down with a busy course load but still manage to hustle for part-time jobs. They want outfits that go from the classroom to the boardroom, maybe with a few tweaks—like adding one of the now-ubiquitous oversized belt bags.
Then we have professionals who are a little further along in their careers but are still searching for work that’s as fulfilling as it is financially sustainable. These adults want to feel and look good in polished, professional outfits, but at the same time, they want these to be pretty “easy” to wear and not overly fussy. This style offers many rewarding aspects, but one of the most gratifying is the unexpected combinations and their daring and practical feel.
I remember one day when I was really crunched for time between meetings. I opted for a look that was kind of the opposite of an all-timer image I might create with the incredible pieces in my wardrobe. I mixed a pair of impeccably tailored trousers with a soft, oversized street-style sweater and some rugged boots (I call this look “urban balance”).
The same rebelliousness I have when I create an outfit that’s more about real life than image comes through here in the use of “unexpected” combinations. Moments like these remind me that street style is as much about adaptation as it is about aesthetics. The modern street style is essentially democratic.
There is no single template, no rulebook to follow—just a shared understanding that dressing well should be accessible to everyone and true to oneself. It’s about using style as a means of self-expression and the well-placed accent or unexpected color combination that doesn’t need a lengthy explanation to justify it. If there’s any rule about street style, it’s that you can make your own rules, not only from one season to the next but also from one day to the next.
Daily life on the streets, whether enjoying a leisurely weekend walk in Brixton or enduring a nonstop workday in the City, reinforces the idea that style is a vital, vibrant expression of life itself. It is something that, like the seasons, mood, and resilient urbanity, seems always to be on the verge of changing. It is this pulsing street energy that makes one pay attention to how real fashion evolves and responds (or fails to respond) to real-life urgencies—an ensemble here, an outfit there, all somehow and, in some way, together or apart, forming an expression that feels as right for the moment as it is destined for the next moment.
When it comes to social media, the view it provides of what it truly means to be fashionable is often a distorted one. That makes it all the more necessary for young people today to consider the genuinely urban approach to dressing as something to emulate. Not only is that approach visually refreshing; it also carries an empowering message.
The urban individual becomes the everyday person who is also the muse, the critic, and the trendsetter all at once. And while the high-end fashion magazines offer a curated, if not overly pretentious, view of style, the true essence of street style lives in its spontaneity and imperfection, the places where that look and this life intersect. To be street-savvy in today’s world means committing to practicality, with a keen eye for detail, and embracing the unpredictable nature of urban life.
It means curating a wardrobe that’s as multifaceted as the city itself. It means dressing for a fresh canvas that every day provides, in a way that both reflects your identity and celebrates the world around you. For those who share a passion for an authentic, relatable style, there’s no better time than now to experiment, adapt, and redefine what it means to dress well on the streets.
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