Three weeks ago, I got an email from a reader named Mike in Cleveland. “I’ve been reading men’s style blogs and magazines for five years,” he wrote, “and I’ve spent thousands following their advice. But I still don’t feel like I dress well. What am I doing wrong?” Attached was a photo of his open closet—a sea of blue shirts, gray trousers, brown shoes, and an impressive collection of what I can only describe as aggressively tasteful ties. All technically “correct” by standard men’s style rules. All utterly forgettable.
Mike’s situation crystallized something I’ve been grappling with for years: the fundamental problem with most men’s fashion advice. It’s not that it’s wrong, exactly. It’s that so much of it is perfectly right in all the wrong ways.
As someone who’s been dishing out style guidance for over a decade, I feel a growing responsibility to acknowledge a hard truth—much of what passes for men’s fashion advice is problematic at best and counterproductive at worst. It’s created generations of men like Mike, who follow all the “rules” but end up with wardrobes that neither excite them nor actually serve their real lives.
So let’s talk about what’s broken in men’s style advice and how to filter the genuinely useful information from the noise.
The first and most glaring problem is what I call “aspirational disconnect”—advice divorced from how men actually live. Open any men’s magazine or style site and you’ll find recommendations seemingly written for someone who splits their time between corporate boardrooms and yacht parties, with maybe the occasional safari thrown in for good measure.
The classic example is the “essential blazer,” which appears on every must-have list despite being functionally useless for huge swaths of American men. If you work in tech, construction, healthcare, education, or most modern offices, a tailored navy blazer is about as essential as a top hat. Yet the advice persists, creating closets full of rarely-worn items purchased out of some vague sense of obligation to “being a well-dressed man.”
I recently analyzed the “10 Essential Pieces Every Man Needs” articles from seven major men’s publications. The overlap was revealing—every single one included a navy blazer, dark denim, white dress shirt, and brown leather shoes. Not one mentioned workout clothes, which most men wear far more frequently than blazers. Only two mentioned anything related to outerwear for inclement weather, despite this being literally essential for survival in many American climates.
This brings us to the second major problem: the stubborn persistence of class performance in men’s style advice. So much “timeless” guidance is actually about signaling social position through coded markers—the hand-stitched lapel, the Goodyear-welted shoe, the “proper” proportions of a spread collar. These aren’t actually about looking good; they’re about looking like you belong to a particular social stratum.
There’s nothing inherently wrong with appreciating craftsmanship or traditional details. The problem comes when they’re presented as universal rules rather than stylistic choices with specific sociocultural contexts. When publications insist that certain details are “correct” while others are “mistakes,” they’re often just reinforcing class boundaries rather than helping men develop genuine personal style.
This elitism extends to recommended brands and price points, creating the impression that dressing well requires substantial financial investment. The reality? I’ve seen guys look amazing in thrifted $30 suits tailored for $75, while others look awkward in $3,000 designer outfits. Budget certainly expands options, but it’s never the determining factor in whether someone dresses well.
Then there’s the curious time warp that most men’s style advice exists in—perpetually stuck somewhere between 1962 and 1967. Don Draper casts a long shadow, apparently. While other areas of design continually evolve, traditional menswear advice remains suspiciously static, creating weird anachronisms like recommending pocket squares to guys who work in open-plan tech offices where even wearing a collar is considered formal.
This nostalgia extends to lifestyle assumptions that haven’t been broadly relevant for decades. How many modern men actually need a tuxedo, or attend events where pocket squares aren’t costumey, or wear different shoes for day and evening? Yet these concepts persist in style guides, creating an alternate reality where men are constantly attending garden parties and changing for dinner.
Perhaps the most insidious problem is the fundamental premise underlying most style advice—that there is one objectively “correct” way to dress well. This notion of universal rules not only ignores the rich diversity of cultural expressions in menswear but also strips the joy and creativity from personal style.
Traditional menswear advice often treats fashion as a problem to be solved rather than an opportunity for self-expression. Follow these rules, avoid these mistakes, buy these specific items—and you’ll be “doing it right.” This approach might produce technically correct outfits, but it rarely results in genuine style, which emerges from the relationship between clothing and the individual wearing it.
So if traditional advice is so problematic, how do we filter what’s actually helpful? Here’s my framework for cutting through the noise:
First, interrogate the context. When reading style advice, ask yourself: Who was this written for? What lifestyle does it assume? What social signals is it trying to send? Many “rules” make perfect sense in specific settings (like traditional business environments) while being completely irrelevant in others. Understanding the context lets you translate advice to your actual circumstances rather than adopting it wholesale.
For example, the classic advice about matching leather colors makes sense for formal business attire but becomes needlessly restrictive for casual wear. Similarly, guidelines about suit proportions are useful if you regularly wear suits, but pretty meaningless if you don’t.
Next, distinguish between practical and symbolic advice. Some style guidelines have functional bases—like wearing fabrics appropriate for the season or choosing shoes that properly support your feet for their intended use. Other “rules” are purely about signaling cultural literacy in specific circles—like never buttoning the bottom button of a suit jacket or understanding the subtle hierarchy of dress shoe formality.
Both types of advice can be valuable, but it’s important to recognize which you’re dealing with. Practical advice generally translates across contexts, while symbolic rules are only relevant if you’re trying to send those specific signals to audiences that can read them.
I find it helpful to categorize style advice into three tiers:
Technical advice concerns construction, fit, and functionality. This tends to be the most universally applicable—clothes should fit your actual body, construction should be appropriate to intended use, and materials should suit their purpose. When traditional style sources talk about suit shoulders that accommodate your frame or shoes constructed for longevity, they’re generally on solid ground.
Social advice concerns contextual appropriateness and cultural literacy. This is highly dependent on your specific environment and goals. Guidance about dressing for job interviews, black-tie events, or particular social settings can be valuable if those situations are relevant to your life—and completely irrelevant if they’re not.
Aesthetic advice concerns subjective matters of taste presented as objective rules. This is where traditional menswear advice most often goes astray, insisting on “timeless” combinations or “correct” proportions that are actually just stylistic preferences from particular eras and subcultures. Take these with an enormous grain of salt.
Perhaps most importantly, evaluate advice based on outcomes rather than adherence to rules. The ultimate test of any style guidance is simple: Does following it help you dress in a way that makes you feel confident and appropriately dressed for your actual life? If not, it’s not serving its purpose, regardless of how authoritative the source.
This outcomes-based approach helps explain why some of the most useful style advice comes from unexpected sources. Some of my favorite guidance has come from costume designers, who focus on how clothing expresses character and fits into specific contexts rather than abstract notions of correctness.
It’s also worth seeking advice from diverse sources with different perspectives. Traditional menswear has been dominated by a narrow slice of cultural experience, primarily white, upper-middle-class, and Euro-centric. Expanding your influences introduces new possibilities and challenges assumptions about what “works” or doesn’t.
So what might better style advice look like? Here are the principles I try to follow in my own writing:
Start with the individual’s actual life, not an imagined ideal. Effective style begins with honestly assessing where you live, what you do, who you interact with, and what you value—not with someone else’s template of “essential” items.
Recognize that context determines appropriateness. There’s no universally “correct” way to dress, only options more or less suited to specific environments and purposes. A perfectly tailored suit can be just as inappropriate in some settings as cargo shorts would be in others.
Focus on principles over prescriptions. Rather than providing rigid rules or must-have lists, good advice offers frameworks for making choices—like understanding how color and proportion affect perception, or how different elements work together to create coherent expressions.
Emphasize personal comfort—both physical and psychological. Clothes that pinch, restrict, or make you self-conscious will never look good, regardless of how well they follow “the rules.” The best-dressed people wear clothes, not the other way around.
Treat style as an ongoing conversation rather than a fixed destination. Our bodies, lifestyles, and identities change throughout our lives. Our relationship with clothing should evolve accordingly rather than aiming for some perfect, static wardrobe.
So what happened with Mike from Cleveland? After seeing his closet photo, I didn’t send him another list of essential items or style rules. Instead, I asked him to send photos of people whose style he admired, outfits he’d felt most confident wearing, and a realistic breakdown of how he spent his time. His response revealed someone whose actual inspirations—more casual, textured, and contemporary than traditional menswear—were completely disconnected from the advice he’d been following.
Two months later, he sent an update with a photo of his newly edited wardrobe—smaller but more cohesive, with pieces that worked for his creative-leaning workplace and active social life. “For the first time,” he wrote, “I feel like my clothes are actually mine, not some version of myself I thought I was supposed to be.”
And that, ultimately, is what good style advice should do—help you become a more authentic version of yourself, not someone else’s idea of who you should be. It should expand possibilities rather than constrain them, offering tools for self-expression rather than rules for conformity.
The finest-quality made-to-measure suit in the world is a failure if it sits unworn in your closet. The “incorrectly” styled outfit that makes you feel amazing and suits your actual life is a triumph, regardless of what any style guide might say. The sooner we recognize this fundamental truth, the sooner we can develop style advice that actually serves the men who read it, rather than some theoretical ideal that exists only in magazines.
So the next time you read a breathless piece about the “10 Shoes Every Man Must Own” or “Style Mistakes You’re Definitely Making,” remember to filter that advice through the reality of your own life. Take what serves you, leave what doesn’t, and never forget that genuine style isn’t about following rules—it’s about knowing which ones matter to you and why.
