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.

As a result, when it comes to dressing, they must always be regarded at face value. They are ideas rather than the last word on style. But excellent advice is never to be dismissed, and as menswear grows more rich and varied, more experimental and bountiful, more trend-aware, having a valuable fall-back position that cuts through the clutter can aid in moments of difficulty and self-doubt.

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 they’re often overlooked; a performance for a good fit, high quality, versatility, good value, lack of extremes, and keeping it sober.

There are undoubtedly many more rules than those presented here. Some of these you may have discovered on your own. After all, it is part of the fun of dressing, which no law should take away: putting on new clothes, seeing if they fit you, and seeing how they make you feel. However, these standards have withstood the test of time and, when combined, serve as a foolproof guide on how to dress properly today.

1. Wear a suit well

Fit is the key to making a suit appear good. According to Davide Taub, head of bespoke suits at Savile Row tailor Gieves & Hawkes, if you're buying off-the-peg, focus on the fit across the shoulders because getting the chest and waist changed is a reasonably easy process. “Be cautious about wearing a period costume unless you're going for a comprehensive period appearance since the suit starts to look like a curiosity in isolation,” he advises. Classic is the best and most useful – dark, two-bottoms, 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.”Aesthetic, useful, and robust sports versions go with everything and can withstand the rigors of everyday wear. However, a watch must still fit you. It should feel comfortable and be the proper size and depth for your wrist — 40mm is called the ‘Goldilocks' size.

3. Don’t shy away from color

Whether it’s on casual wear or formalwear, indulge in a bit of color. “Most men are unjustly scared of it – they’re intimidated by anything that isn’t navy or grey”, says menswear designer Oliver Spencer. “But color can be timeless too.” A green suit, for example, can look particularly rakish, while Spencer recommends pinks, greens, mustard, and brighter shades of blue as particularly versatile year-round colors that will lift your entire outfit. However, when it comes to color, he believes that little is more: “You just need a bit of it, in one garment.”

4. 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 color, the pattern, the sole – you don’t want it fussy. Anything fussy may look good now but will look strange very quickly.” “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.”

5. Keep accessorizing to a minimum

Accessories like ties and pocket squares bring individuality to classic clothing, but be careful how you use them. “It’s best to harmonize them with what you’re wearing by picking out a color 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.”

6. Dress for the setting

Style is more than just self-expression; it is also about dressing appropriately for your surroundings. Consider clothes to code: you need the appropriate combination to function with the situation, whether it's a formal dinner or a leisurely Sunday in the pub. The worst style is one that is inappropriate. Is this some sort of conformity? No, as one of Tom Ford's many fashion quips indicates, it's a sign of respect for others. Also, how do you feel at ease in your own skin? When in doubt, dress up.

7. Buy a Dinner suit, never hire

Occasions for the highest level of formal attire may be infrequent, but they are all the more demanding as a result. So, while it may appear to be an extravagance at first, having a dinner suit that fits you rather than hiring one makes more sense after a few years of use. “With hiring, there’s always the risk of the wearer looking almost childlike while dressed in some oversized, boxy ensemble,” warns Toby Lamb, design director of contemporary tailoring label Richard James. Own as classic a dinner suit as possible: in midnight blue, single-breasted, with satin lapels and trouser seams. And it goes without saying you should learn how to tie a bow-tie yourself.

8. Don’t Skimp on glasses

Invest time into finding the right spectacles for you. “People spend an average of seven minutes picking a pair that will define them for the next three or more years,” notes eyewear designer Tom Davies. “Poor choice and poor fit are why so many people learn to hate their glasses.” Buy what you feel good in, taking into account your face shape but considering the top line of the frames’ relation to your eyebrow shape – team straight with straight, curved with curved – and your hairstyle. Buy wisely too, says Davies: there’s no point buying cheap frames and being up-sold on expensive lenses because the frames will look tatty soon enough anyway.

9. Know when to break the rules

Know when to follow clothing codes, such as black tie, and when to defy them. Some are there for a good reason, either because the situation calls for it or because a higher authority — your supervisor, for example – expects it. However, as Drakes' Hill points out, “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.”