Why Do Most Men Dress So Poorly?

Last week, on the metro, I passed a man in his late thirties, well dressed, shirt impeccably pressed… and wearing white sneakers on his feet. That’s a no, no and no… This kind of contrast, we notice it instantly in others, even if we don’t always catch it in ourselves. You might tell me he perhaps had dress shoes waiting at the office, but I doubt it, since more and more men are pairing sneakers with a suit these days, a habit that traces back to the casual style typical of Silicon Valley. And yet, we’re right in the middle of “Montreal Fashion Week,” now rebranded as the M.A.D Festival. And this event, like others of its kind around the world, raises a simple question: what’s the point of these if their influence never actually reaches the average man’s wardrobe? I was also chatting about this with Stéphane Le Duc, fashion columnist and host of the interview with Clara Tosi Pamphili that I’ll get to further down, trying to figure out why most men dress poorly. It’s hard to pin down a clear answer, but I’ll offer a few pointers to help change that perception and figure out whether your own style needs work.

Style, fashion and elegance: are they the same thing, or different?

Before anything else, know that I haven’t included any bad style choices in the images illustrating this article, and that’s intentional: the idea is not to give you bad habits, but to show you the right ones.

I personally believe the three concepts named in the subheading each deserve their own explanation. Fashion is often a fleeting thing that changes constantly, so keeping up with it means spending constantly, and the results of any given trend tend to wear off quickly. We see proof of this in the fact that most designers and major houses release two collections a year, not only to showcase creativity, but for commercial reasons: so that you, the consumer, keep spending, and the company keeps turning a profit and stays afloat. It’s an endless cycle. You need to put a stop to it in your own head, and only buy what you actually need.

Style and elegance belong more to the same family. Both words reflect timelessness, which, to me, is the key when buying a piece of clothing. Just take a look at the men at Pitti Uomo, or in Milan in general: their looks are rarely exuberant or eccentric. Instead, the outfits tend to be sober, and it’s the accessories that set them apart and make them stand out.

I was actually at the Italia è Moda exhibition this week, running until August 23 at the Fairmont Le Reine Elizabeth, as part of the second edition of the “Italian Fashion Days in the World.” Curated by Clara Tosi Pamphili and staged like a theatre set, the exhibition presents clothing and accessories following the rhythm of everyday life: daywear, eveningwear and sportswear. From tuxedos to tracksuits, evening gowns to contemporary pieces by young designers, alongside leather goods, footwear (including gorgeous Santoni shoes), eyewear and cosmetics, the exhibition offers a full panorama of Italian fashion and design. The pieces on display had a real influence on this article, because even though they’re simple, it’s the way people put them together that makes them elegant. I also had the chance to attend a very informative interview with her afterward, on Italian style and its influence on the fashion world.

I also think dressing badly is a very Québec, even North American, thing. When I was a kid, my mother would often ask, “Where do you think you’re going dressed like that?” Even though I thought I was dressed “nicely.” I wonder if that isn’t tied to the fact that, when she was young, religion was everywhere, and church was one of the few occasions where people actually dressed up. Outside of that context, it simply didn’t have a place… ah, that Judeo-Christian complex that still haunts us!

Gentlemen, keep in mind you’re not teenagers anymore

I asked a friend who spent years working in fashion for a few pointers on what, in her view, makes most men dress badly. She told me right away that a lot of men never evolved, and are still stuck with a teenage sense of style. The clothes are ill fitted and badly finished, with pants that are too long and too baggy, giving a sloppy appearance. Shirts with oversized patterns, too big, with too much room around the collar, that put the brand front and centre and hide your personality behind the garment. Some men try to hide extra weight in baggy clothes, but it backfires, they end up looking even bigger. It’s as if, for a lot of men, clothing is more of a utilitarian function than a way to be elegant. Your life has changed; your clothes need to catch up with your new lifestyle.

None of this means you need to spend a fortune on clothes, far from it. A grey sweater and a pair of denim pants can make for a perfectly elegant outfit or a completely inelegant one, if you’re careless about how you wear it (you don’t want to end up looking like the Michelin Man). Sometimes all it takes is a good fitting at a tailor’s, or simply choosing the right size not the size for the body you hope to have in five years, or the one you had five years ago.

Fit isn’t just a matter of size, it’s also a matter of proportion. A blazer, shirt or pair of pants that fits a friend perfectly won’t necessarily suit you the same way, because your build isn’t his. A shorter man will benefit from avoiding oversized patterns or jackets that run too long, which crush the silhouette. A more heavyset man should favour structured cuts over baggy ones, which elongate the line instead of adding bulk. Knowing your own build isn’t about vanity, it’s the foundation for making sure any garment, however simple, actually fits well. We touched on this, in fact, with Jean-Michel Bonin, owner of Clusier, in our article on custom-made clothing.

Buy for the future, sure, but not for an unrealistic physical goal you’re not actually prepared to put in the work to reach. Yes, I know that last part can be a tougher call to make, and can sting the ego a little.

Can’t find your style, or feel uncomfortable with advisors putting too much pressure on you? Don’t hesitate to hire a stylist, ideally someone independent, not affiliated with a particular shop or mall.

Another reflex a lot of men lack: knowing how to match colours together. You often see combinations that clash, or the opposite, outfits that are entirely colourless, all black, grey or navy, out of fear of getting it wrong. The fix isn’t complicated: build your wardrobe around two or three neutral colours (grey, navy, beige) that pair easily with one another, then add one or two accent colours through your shirt, tie or accessories, like an analogue watch (we’d recommend a visit to the professionals at Château d’Ivoire or Time Vallée). You don’t need to be an expert in colour theory, just consistent, and not afraid of a little boldness, in small doses.

Holding on to clothes for too long: a bad habit

A worn-out garment worn in public has no place. A frayed collar, a faded colour, a fabric that’s started to pill: these are all clear signs it’s time to move on. If you want to hang on to it, put it to use for manual labour or yard work. If it’s not being used, donate it or recycle it, plenty of organizations and thrift shops will give it a second life.

The same principle applies to accessories and footwear. If a belt is worn out, replace it. Shoes that no longer do your style justice should go to a cobbler for repair, if possible: a resoling job often costs a fraction of a new pair, and can add years to a good pair of leather shoes. This is exactly where investing in quality pieces from the start pays off: a well-made garment can be repaired, a cheap one just gets thrown out.

Let’s talk about shoes…

Ah, the suit-and-sneakers combo I mentioned in the intro… is there a worse style mistake? I don’t think so. This trend actually got its start in the 1980s, with people wearing sneakers for a comfortable commute before changing into dress shoes once they got where they were going. But it became the norm once the tech industry came along, looking to break free from the traditional codes of the business world, and was later picked up by the advertising world, which became something of a sister industry to tech, and eventually by major fashion houses, which started producing sneakers at outrageous prices. Call me old school if you want, but sneakers or anything with a white sole, I’d rather save those for a run or a more summery outfit. I think this bad habit, prioritizing comfort over elegance, is part of what’s dragging down men’s overall class. I’m guessing plenty of you are guilty of this too, but hey, that’s just my opinion. On top of that, the big issue with sneakers is that they’re often disposable and don’t last long. They’re practically impossible to repair, and cleaning them properly comes with an outrageous price tag. In the end, the shoe ends up in the same state regardless, especially the sole, which is often plastic, wears out quickly, and can’t be replaced.

Beyond just skipping the sneakers with a suit, it’s worth knowing how to choose the right shoe for the occasion. The oxford remains the most formal option, with its closed lacing, perfect for the office or a dressy evening out. The derby, with its open lacing, offers a bit more versatility and pairs well with a more casual jacket. Always go for genuine, high-quality leather, not bonded leather or shoes labelled “genuine leather,” which is often a misleading term for lower-end quality. Two or three pairs of well-made, well-maintained shoes will last longer, and be more comfortable, than half a dozen cheap ones.

And once fall arrives, the boot becomes the gentleman’s ally, as long as you don’t mistake it for a work boot or a hiking boot. We’ve actually put together a full guide on the best autumn boots to help you choose, a decision that deserves just as much care as picking out a dress shoe.

A few more tips to elevate your style

As for me, even though I haven’t yet bought a suit (an expense I haven’t allowed myself just yet, since a good chunk of my savings is going toward this platform), I do already own a tuxedo, and I still try to be elegant by choosing pieces that will keep my style timeless and serve me over the long run. To find inspiration, I look to menswear content creators, particularly Europeans. Americans tend to default to Suitsupply (an entry-level suit brand) and Ralph Lauren (whose logo tends to be everywhere), largely thanks to sponsorships. You can also look to James Bond for inspiration, though his suits can sometimes run a little too tight, so it’s better to focus on the style itself rather than how it’s worn, and above all, adapt it to your own everyday life.

Working with a tighter budget? Choose pieces that are well sewn, well tailored and well made. Keep an eye out for sales, they can be tempting, but make sure the colours, styles and sizes actually match your taste and your wardrobe. Don’t hesitate to ask yourself how many times you’ll realistically wear the piece you’re about to invest in.

Be yourself, not a magazine cover

Don’t forget that the first impression you give through your clothes is often the one people remember. Whether it’s for a date or a professional meeting, it’s your calling card. Don’t be afraid of looking “overdressed,” own your style, be confident, dare to try new colours and new cuts, and above all, find a style you’re comfortable in, one that gets noticed for the right reasons.

If you only take away a few key points from this article, here’s the essential:

• Timelessness over trends. Invest in pieces that will stand the test of time rather than what’s popular this season.
• Fit above all else. A garment well tailored to your current build beats a piece from the right brand that doesn’t fit properly.
• Colours, with consistency. Build around neutrals, then dare one accent at a time.
• Dress shoes, not sneakers. Save the sneakers for sports or very casual settings, never with a blazer.
• Upkeep, as a discipline. A worn garment, a damaged sole, a frayed belt: these get repaired, replaced, never worn as is.

At Gentologie, our mission is to help every man become a gentleman. And when it comes to clothing at least, that often starts with something simple we like to repeat: style over trends, always. To start your journey toward a timeless style, join the Club by Gentologie and get a discount on your first purchase at our partner Clusier, a menswear shop in Old Montreal carrying timeless brands like Canali, Gran Sasso, and many others.

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