Has menswear got messier? Yes, but with good reason

SINGAPORE – For a long stretch of the past decade, the ideal man – at least the one who lived on social media – looked immaculate.

His hair was trimmed into precise gradients. His wardrobe consisted of disciplined neutrals: sand, black, cream, navy. His trousers fell at mathematically approved lengths above spotless sneakers. His apartment contained exactly three design objects, all of which had likely been purchased after watching a YouTube video titled 10 Things Every Man Should Own.

That was the era of the clean boy. Or the minimalist man. Or whichever algorithm-friendly variation one prefers to call it. The point was not merely dressing well; it was appearing frictionless. Style was presented as a solvable equation: Buy these five items, follow these grooming rules, lift these weights, achieve this symmetry.

But then, society turned a corner, letting out the grime and the unpretty. Across runways, social feeds and street-style photos, that immaculate archetype has begun to unravel – sometimes literally. Shirts are wrinkled, jackets hang off sloping shoulders, denim looks suspiciously pre-destroyed and layers slapdash, as if thrown together in dim lighting.

Gents, take this as a welcome to the rise of the “messy boy” aesthetic.

From uniform to individual

The term itself is less important than the mood it describes: an undone, slightly chaotic approach to menswear where polish takes a back seat to personality. In this world, hair looks slept in, shirts remain half-tucked and once-starched tailoring now slouches off the frame. Pristine exits as the spotlight shines on the chaotically mismatched.

It is a look that is as much a way of dressing as it is an attitude switch. And if the clean era once aspired to perfection, messy boy thrives on the opposite impulse: the pleasure of looking a little bit unfinished.

Fashion has always moved in cycles between order and disorder. After several years dominated by quiet luxury, capsule wardrobes and algorithm-approved basics, the pendulum has swung again – this time towards something looser, stranger and faintly chaotic.

On the runways, the mood has been unmistakable. At DSquared2, twin brothers Dean and Dan Caten’s Spring/Summer 2026 showcase resembled the contents of a particularly adventurous wardrobe explosion: leopard print with chainmail scarves; overwashed track jackets against delicate lace; garments layered with the enthusiasm of someone who had run out of hangers.

Japanese label Doublet pushed tailoring into droopy territory, with slouching jackets, sun-faded fabrics and shoulders that appear to melt downwards rather than stand square. The result feels charmingly off-kilter, as if traditional menswear codes had been left outside in the rain.

Then there was Maison Mihara Yasuhiro, whose Spring/Summer 2026 runway show approached everyday dressing with a sense of playful sabotage. Striped shirts arrived deliberately wrinkled, while jeans appeared splattered with paint.

Once cosy, cardigans strode down the runway containing a web of strategically placed holes, as if to celebrate the effects of time and a moth-infested wardrobe. Letterman tees delivered slogans that sound like they were muttered under someone’s breath at 3am.

The clothes read as a parody of normality – recognisable, but skewed just enough to suggest mischief and irony.

None of this is accidental. Messiness, in fashion terms, is rarely the absence of thought. It is the performance of effortlessness, which paradoxically requires quite a lot of effort.

For designers such as Ethan Lee, founder of the Singapore-based label Fassbender & Mellon Collie, the aesthetic reflects a broader cultural mood.

Lee, whose pieces are stocked at Dover Street Market Singapore, describes the look as an expression of rebellious nonchalance, one shaped by a generation increasingly sceptical of traditional aspirations.

“I think it resonates with the current state of the world,” he says, pointing to the lingering hangovers of economic uncertainty and global instability.

“It feels like people just don’t care any more. The younger generation’s done with trying to live ‘The Dream’. Why bother working a nine-to-five? Why please the older generation by looking clean, prim and proper?”

In this context, appearing slightly dishevelled can function as a quiet act of rebellion. Lee sees the aesthetic echoed across contemporary pop culture – from the chaotic styling of television series to the internet’s fascination with offbeat personalities who appear indifferent to conventional polish.

The message is clear: Perfection is beginning to feel suspicious.

Trend forecasters Tim Gates and Nihan Arici of BDA London frame the shift in similar terms.

According to them, the messy boy aesthetic reflects a return to something more lived-in and emotionally honest. As macroeconomics and societal pressures weigh on younger generations, the appeal of clothing that feels “real rather than overly curated” has grown in its appeal.

Highly polished aesthetics, they note, have begun to carry associations with privilege and performative perfection – visual signals that can feel increasingly detached from everyday life. In response, many younger consumers are gravitating towards clothing and aesthetics that communicate individuality and spontaneity instead.

The look also dovetails neatly with the rise of resale platforms and repair culture. Garments that show wear – faded denim, patched jackets, fraying hems – carry a sense of history. They look like they lived a life before arriving in your wardrobe.

Against the algorithm

But there is another dimension to the messy boy phenomenon – one tied less to economics and more to the strange aesthetics of the digital age.

The internet has been steadily moving towards visual perfection, with artificial intelligence at the steering wheel. Filters smooth skin, while editing apps sharpen proportions. AI produces images where everything appears impossibly symmetrical and gleaming.

The result is a peculiar form of visual fatigue: When every image is immaculate, immaculate stops feeling interesting.

Against that backdrop, the messy boy look functions as a subtle refusal of algorithmic polish. Wrinkled fabrics, awkward layering and imperfect proportions act as visual proof of human intervention because they signal that a real person, not a machine, assembled this outfit.

Ibiza-born, London-based content creator Olaf Hernandez has watched the shift unfold first-hand. Early in his social media career, he admits, the dominant aesthetic leant heavily towards perfection: outfits that looked polished, controlled and impeccably styled. More recently, however, his audience has responded enthusiastically to looks that feel looser and purposefully undone.

“The messy boy aesthetic feels like the opposite of (polish),” says Hernandez. “It’s more relaxed, a bit imperfect, and it allows personality to come through and connect more with the public.”

Interestingly, those “imperfect” outfits often generate stronger engagement. Viewers respond to them because they resemble real life rather than editorial fantasy. When something appears slightly chaotic, Hernandez notes, it feels relatable.

Jesper Chai, a Singapore-based model at local agency Basic Models whose personal style leans into messy boy territory, describes the appeal in similar terms. The look, he says, carries a sense of humanity that polished styling sometimes lacks.

“It’s like leaving the house with your shirt half-tucked, hair a little messy, mixing pieces that technically shouldn’t work together, but somehow do,” says Chai.

But the illusion of spontaneity can be deceptive because even the most casual-looking outfit often involves careful decisions about proportion, texture and layering. “It might appear effortless or accidental,” Chai says, “but there’s usually a lot of thought behind it.”

Push and pull of messy

And it is this paradox that sits at the heart of the messy boy aesthetic. The look suggests carelessness, yet the best versions of it are quietly meticulous. The right slouch in a jacket sleeve; the correct amount of rumpling in a shirt. There is a delicate balance at play between looking interesting and looking like you actually slept on the train.

Designers understand this tension well.

Speaking to Harper’s Bazaar Singapore, Milan-based brand GR10K, known for its workwear-inspired collections that approach volume and looseness from a functional perspective, says it often begins with garments designed for real labour – clothing originally engineered to allow movement and mobility.

From there, it introduces subtle distortions, adding what it describes as “hallucination” to everyday silhouettes. The result lands somewhere between practicality and imagination.

It also highlights another reason messy boy styling resonates today: its relationship with process. Garments appear to be in mid-transformation – patched, dyed, customised and altered. They look like works in progress rather than finished products.

One also has to consider how the aesthetic intersects with shifting ideas around masculinity.

For decades, male dress codes often emphasised control and discipline: tailored suits, clean lines, restrained palettes. The rise of the finance-bro uniform – trimmed hair, slim trousers, minimalist sneakers – extended that ethos into casual dressing as well.

But younger generations appear less interested in those rigid signals. According to designer Lee, the hypermasculine archetype that once dominated menswear culture has begun to lose its cultural grip.

Messy boy styling offers a different visual language, as it allows for vulnerability, eccentricity and emotional expression without requiring the wearer to announce those qualities explicitly. A fraying knit or a paint-splattered pair of jeans can communicate mood in ways that perfectly pressed garments rarely do.

Of course, none of this means that polished dressing is about to disappear entirely. Fashion rarely eliminates an aesthetic; it simply adds new ones to the conversation. In fact, even traditionally refined wardrobes are beginning to absorb hints of messiness.

Forecasters Gates and Arici expect the messy boy aesthetic to evolve rather than vanish. As individuality and self-expression remain central cultural drivers, the visual language of imperfection will likely continue to influence how menswear develops over time.

Which brings us back to the messy boy himself because, in spite of the name, he is not necessarily careless or disorganised, though his wardrobe might occasionally suggest so. What defines him is an instinctive distrust of perfection: He is suspicious of formulas, allergic to uniformity and unbothered by the idea that a shirt might wrinkle during the day.

In a cultural moment increasingly shaped by algorithms, filters and AI, that slight unpredictability can feel refreshing. After all, style has always been more interesting when it looks like a human made it.