5 Essential Rules That Most Stylish Men Forget

Eureka! moments on the well-trodden path to dressing well.
IMAGE Esquire UK

"Know first who you are, and then adorn yourself accordingly."

—Epictetus, Philosopher, 55 AD

While this sage wisdom may have been imparted to the enlightened minds of ancient Greece more than 1,500 years ago, it would appear that we men are slow learners; still prone to scrabbling about in the dank marshes of poor taste and ill-fitting fashion, even now.

But how about those stylish few that are out of the woods, so to speak? How did they manage to elevate themselves above the termite mound?

Epiphanies, that's how. A moment of self-awareness that serves to highlight their folly, leaving a lasting impression. Because even the most style savvy guys have to start somewhere. Just Google 'David Beckham 2001' if you don't believe us.

1 | Realizing that formal shoes don't automatically make every outfit formal, or stylish

Bad Shoes

Burn them.

A more destructive style move than even the much-maligned 'going out shirt'; cast your eyes across the booze-soaked floors of Britain on any given Saturday night and you'll be greeted with a familiar scene: scores of men who have decided to pair formal shoes with whatever casual look they've cooked up; carrying the misguided belief that bright tan Winklepicker = automatic nighttime style win.


Even if your formal footwear happens to be a pair of lifetime-lasting Church's brogues, pair them with a t-shirt and jeans and they'll automatically look out of place. Which is why stylish guys understand that even the best quality pieces require context and setting.

So, if your top half is casual, then opt for a pair of simple, quality leather sneakers or work boots instead. There's no need to overplay it.

2 | That quality trousers and a trustworthy tailor are a good investment

Ben Affleck

Ben Affleck doesn't know how to wear trousers.

You'd think that it'd be easy to chuck some money at trousers and have them fit perfectly right off the rack, but as exhibited by our friend Ben Affleck above, that's certainly not the case.

Some men may well have the build or good fortune to find the right pair straight from the shop, but, if not, this is where well-dressed guys understand the value of a skillful tailor and their ability to transform good trousers into GREAT trousers.

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If you're on the cusp of two waist sizes, opt for the larger of the two and have your tailor go from there. It's much easier for trousers to be brought in as opposed to taken out.

3 | Understanding that putting on a suit isn't a sharp move by default

Daniel Craig

What a turnaround, Daniel.

Forget what you've heard about the 'death of the suit'; a well-cut piece of tailoring is timeless for a reason, but that doesn't mean that wearing any old one makes you the most dapper guy in the room by default.

Too often you'll see a man chuck on a suit with little to no consideration over how it actually feels or fits, mistakenly believing that the very act of wearing one is enough to negate the fact that, actually, it isn't doing him any favors.

Another affliction that can be easily solved by visiting a tailor (there's a reason well-dressed guys have a guy), never fall into the false confidence trap that can come with the wearing of a bad suit.


4 | That wearing 'loud' clothes doesn't make you a modern-day dandy

Paul Pogba

How not to wear bold formalwear.

While we here at Esquire are all for injecting a sense of fun and experimentation into dressing well, it's incredibly easy to veer from 'louche style god' to 'try-hard douche' when it comes to escalating your take on color and print.

Those guys who fall onto the louder scale of the spectrum, while pulling it off, do so because they're confident and wear their clothes with ease and a little ego. It can be painful to see a guy trying to wear a trend or extra loud piece, but actually having it wear him instead.

Not that we can knock them too hard. What with it being part of the epiphany process and all.

5 | That sometimes the simplest outfit is the most stylish

Paul Newman


Paul Newman donning the classics.

Yes, they might be worn best by the likes of Brando, Newman and Gosling, but there's a reason why women will never turn their nose up at a clean white T; slim dark denim and a quality pair of boots.

In a modern fashion landscape where men are bombarded with a constantly evolving zeitgeist; a place where trends come and go in a matter of weeks or months, well-dressed guys understand that sometimes less is more. And that for all the experimentation and Hot New Trends out there, there's a certain timeless solace in keeping things clean and simple every now and again.

This story originally appeared on

* Minor edits have been made by the editors.

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Finlay Renwick
Finlay Renwick is the Digital Editorial Assistant at
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