How To Dress Well: The 9 Rules All Men Should Learn

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.

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.”

Photo: Monofore

“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.

“Most men are unjustly scared of it – they’re intimidated by anything that isn’t navy or grey,” says menswear designer Oliver Spencer.

“But colour can be timeless too.”

A green suit, for example, can look particularly rakish, while Spencer also recommends pinks, greens, mustard and brighter shades of blue as especially versatile year-round shades that will lift your entire outfit.

But he adds that, when it comes to colour, less is still more: “You just need a bit of it, in one garment.”

Photo: A Day’s March

“It’s wider in the thigh, so it’s comfortable, but narrows, so it works with either smart shoes or sneakers,” he advises.

“It’s the best year-round, wear-with-anything, dress up or down style.”

The wise will wear dark, raw denim too and give the pre-distressed a wide berth.

“The whole pleasure of denim is that it ages with the way you wear it. Why miss out on that?”

It’s the kind of advice your mother might offer, but if you’ve invested money and thought in your clothing, look after it.

Have your suit dry-cleaned and pressed; wash your clothes regularly and, ideally, don’t tumble dry them (it can degrade the fabric); and polish your shoes.

Photo: CDLP

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.

Photo: Myrqvist

“The color, 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.

Photo: Drake’s

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.”

There’s are few things less stylish than a man dressed as he thinks he should dress rather than in what he genuinely feels suits who he is.

There are caveats to that, of course: there are no prizes for dressing like a rodeo clown unless indeed you are one.

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.