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How to Dress Well — 8 Rules All Men Should Learn

There are enough rules in life as it is. Some, however, are there to help. Like the rules that govern how to dress well. Of course, every man or woman that has an opinion on such things speaks from personal experience – and no doubt what works for one doesn’t always work for another; in short, one man’s food is another man’s poison.

So, when it comes to dressing, they always have to be taken at face value. They’re tangible suggestions rather than the last word on style.

But good advice is never to be sniffed at, and, as menswear becomes ever more rich and varied, ever more experimental and abundant, trend-aware, in moments of confusion and self-doubt, it can help to have a valuable fall-back position that cuts through the clutter.

These ‘rules’ tend to be founded in history – they’ve worked for generations, so might well be assumed to work well today too. And they tend to be founded in the obvious, so obvious they’re often overlooked: a preference for a good fit, high quality, versatility, good value, lack of extremes and keeping it sober.

There are certainly many other rules out there than are presented here. Some of these you may have already learned for yourself. That, after all, is part of the pleasure of fashion which no rule should hamper: trying a new kit out, seeing if it suits you, seeing how it makes you feel. But, these rules have stood the test of time and, when used in conjunction, act as a failsafe guide on how to dress well today.

Here are 8 ways to dressing well

1. Wear A Suit Well

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Getty

The key to a suit looking good is fit. If you’re buying off-the-peg, focus on the fit across the shoulders because getting the chest and waist altered is a relatively easy job according to Davide Taub, head of bespoke suits at Savile Row tailor Gieves & Hawkes. “Be cautious about wearing a period suit unless you’re pursuing a total period look because in isolation the suit starts to look like a novelty,” he adds. Classic is best and most useful – dark, two-button, single-breasted, moderate in details. “It’s not boring. A suit is a uniform. The idea is to think of this suit as a canvas to build different ideas of individuality around. It’s the way you wear it, not the label inside, that impresses.”

2. Invest In A Watch

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“A watch is like a piece of art,” argues Don Cochrane, managing director of British watch brand Vertex. “Choose it because you love it, not because you think it might make money. Watches are personal, it marks your passage through time. But you also have to be practical.” Aesthetic, functional, rugged sports models go with anything and can take the hard knocks of everyday wear. Yet, a watch still has to fit you. It should feel comfortable and be right in terms of size and depth relative to your wrist as well – 40mm is considered the ‘Goldilocks’ size.

3. Keep Your Underwear Simple

Style isn’t only what everyone else can see. When it comes to men’s underwear, there are two rules to follow. One, novelty prints are not for grown men – “your underwear is not the place to express your ‘personality,” as shirt and underwear-maker Emma Willis notes.

And, two, heavily-branded underwear lacks sophistication. “Of all places where you might have the confidence not to have branding, your underwear should be it,” adds Willis. The style that has best stood the test of time, of course, is the cotton boxer short, likely because (as is the case with linen) they take repeated washing, breathe well and are comfortable against your skin.

4. Keep Accessorising to a Minimum

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Drake’s

Accessories like ties and pocket squares bring individuality to classic clothing, but be careful how you use them. “It’s best to harmonise them with what you’re wearing by picking out a colour or two. Or even to juxtapose them entirely,” says Michael Hill, creative director of men’s accessories brand Drake’s. “What you don’t want is to match them up.”

When it comes to curating shirt and tie combinations, wear your tie or pocket square in a darker shade than your jacket. And don’t overdo the accessories either – if in doubt, think less is more and take one element away. “You’re aiming for an air of nonchalance,” adds Hill. “You just need one point of interest.”

5. Dress For The Event

Style is not merely about self-expression; it’s also about being dressed appropriately for your environment. Think of clothes as being codes: you need the right combination to work with the setting you’re in – and that’s whether it’s a formal dinner or a lazy Sunday in the pub.

The worst style is one that is out of place. Is this a kind of conformity? No, as one of Tom Ford’s oft trotted out fashion quotes explains, it’s a mark of respect for others. And about feeling comfortable in yourself. When in doubt, overdress.

6. Spend Money on Shoes

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Timelessness is about simple design and all the more so with shoes,” argues Tim Little, owner of heritage shoe brand Grenson. “The colour, the pattern, the sole – you don’t want it fussy. Anything fussy may look good now but will look strange very quickly.” Quality shoes — the gold standard being re-soleable Goodyear welted examples — are the kind of investment that should last 15 years or more.

Opt for classic styles such as brogues, loafers, or a plain, dark, five-eyelet Derby on a round-toe last, but don’t forget about finding quality dress socks as well. “It’s the shape of the toe that really counts – and round never goes out of fashion,” says Little. “It’s pointy toes or square toes that look obviously impractical. Nobody has feet shaped like that.”

7. Know When To Break The Rules

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Know when to stick to dress codes such as black ties and know when to break them. Some are there for a good reason, typically because the occasion demands it or some higher authority – your boss, perhaps – expects it. But, likewise, as Drakes’ Hill notes, “we can get too hung up about rules as well, and there’s always a case for ripping them up”. That, after all, is how style advances, little by little. “Enjoy the freedom there is now to make mistakes.”

8. Be Yourself

You are not stylish if you’re not being yourself. It’s easier to mimick someone else’s style because they look really good. But do you look good when you mimick their style?

Whatever you’re wearing, you have to own it. Genuine style icons are those who go their own way with a self-confidence that comes from their clothes being a second skin, not a costume.

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