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; or what works for one is considered too pedestrian or too avant-garde by another. So, when it comes to dressing, they always have to be taken at face value. They’re solid 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, ever more 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 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 discovered for yourself. That, after all, is part of the pleasure of clothing, which no rule should hamper: trying 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.
1. Wear A Suit Well
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 Wisely In A Watch
“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.” Aesthetically, 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. Don’t Shy Away From Colour
Whether it’s on casualwear or formalwear, indulge in a bit of colour. “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.”
4. Wear In Your Jeans Until They Are Yours
The all-time most useful cut of the world’s most popular garment, according to Alex Mir, co-owner of Sheffield-based label LinkText, is ‘slim-tapered’. “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?”
5. Look After Your Appearance
It’s the kind of advice your mother might offer, but if you’ve invested money and thought in your clothing, look after it. Use wooden hangers for shirts and shoe trees for your best shoes; 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. Equally, it’s not just the skin of your leather jacket that you need to care for, the same goes for the one you wear everyday. Establish a simple, but no less solid, grooming regime, brush your hair and cut your nails. After all, the devil resides in the details.
6. 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, breath well and are comfortable against your skin.
7. Spend Money On Shoes
“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. “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.”