How to defy conventional thinking on dress codes – and still look like you know what you’re doing.

Now, don’t get us wrong: style rules exist for a good reason. They’re a vital safety net. Especially for those who have more of a, shall we say, cursory interest in fashion (which is absolutely fine by the way, there are other things in life, after all). Yes, we’ve all benefited from style directives at some point in our lives, whether by avoiding embarrassment in the workplace, successfully navigating the dress code at a fancy restaurant or simply knowing how to match a shirt and tie.

So, why break them? For one thing, a lot of these rules were invented decades ago to help men conform to societal norms that are simply no longer relevant. Also: you can only get so far in life by blindly following the rules. Anyway, as these six gentlemen demonstrate, if you want your style to be a true expression of who you are, then it’s perfectly acceptable to start thinking – and dressing – for yourself. You have to know the rules to break them, of course, but sometimes break them you must. Especially if you want to be papped outside fashion shows.

In what might be the clearest modern example of the cyclical nature of trends, socks and sandals – until recently the preserve of retired holidaymakers – are now the toast of the fashion set. Who do we have to thank for this remarkable volte-face? None other than Prada, whose fresh take on the socks-and-sandals look for SS17 made us all wonder why it was ever so controversial in the first place. One word of advice: if you do opt for white socks, as in the case of this urban wanderer, invest in some good ones – old gym socks are not OK.

“Tuck your shirt in, young man.” It’s one of the first pieces of style advice that we receive, but is it worth following? It makes sense if you’re wearing a suit, of course, but in less formal situations there are plenty of arguments for leaving your shirt fully – or, in the case of Mr Alexandre Mattiussi of AMI, shown here on the left – partially untucked. For one, a tucked shirt worn without a jacket can serve to draw attention to the waistline, which is not a virtue for most men. For another, a tucked shirt rarely stays tucked. Sit down, bend over or lift your arms above the height of your shoulders and your shirt tails will inevitably balloon above your belt, leaving you with an unflattering muffin-top. Yes, you could wear shirt stays, which are essentially inverted suspenders for men. Or you could save yourself the bother by just not being so prissy about the whole thing.

We’re often told that the most important consideration when choosing clothes is how well they fit. But, what does that actually mean? Fit, silhouette, proportion: these are the variables by which the big movements in style are defined. A jacket that “fits” by today’s standards might well look ridiculous in a couple of decades’ time. Mr Thom Browne broke every tailoring rule in the book when he set about redefining the male silhouette in the mid-2000s; designers such as Messrs Craig Green, Demna Gvasalia and Alessandro Michele do similarly radical things with proportion today. The take-home lesson? Don’t be afraid to experiment with size and shape. Try things one size too big and see how it looks. This picture clearly shows the effect that a cropped, boxy jacket and generously wide trousers can have on your frame.

In 1951, Mr Bing Crosby was very nearly turned away from a hotel in Vancouver on the grounds that he was wearing denim. Levi Strauss & Co heard about this story, designed a denim tuxedo for Mr Crosby and presented it to him at a rodeo event in Elko, Nevada. So was born the legend of the “Canadian tuxedo”, otherwise known as double denim, an outfit that continues to polarise opinion to this day. We’re firmly in the yes camp – assuming it’s done properly, of course. While the safest approach is to pick two different washes, the jury’s out on whether this approach really qualifies as double denim proper. If you’re planning on going all-out, the trick is to treat it as you would any other outfit with a large expanse of one colour and find a way of breaking it up. A crisp white T-shirt is a great way of adding contrast, as is the light-grey herringbone overcoat that the gentleman in this picture is wearing.

“Blue and green should never be seen” is surely an example of the rhyme-as-reason effect, a cognitive bias that makes us more likely to believe statements that have a poetic quality to them. Why else would people be so violently opposed to seeing these two colours together? Consider the gentleman in this picture, whose outfit of a fern-green bomber jacket and blue shirt makes a compelling case for establishing another, competing rhyme: “Keen to be seen? Wear blue and green.” Here’s hoping that it catches on. While we’re on the topic of underrated colour combinations, navy and black work well together, too. “You’re on the right track with navy and black.” We could do this all day.

Should you wear a pastel-blue printed shirt with green camouflage shorts? Absolutely not. Should you take our advice as gospel? Absolutely not. We’d have to be blind to miss the irony in an article entitled “Six Style Rules To Break This Summer” that itself comes across as a set of rules, so we’ll finish by encouraging you to remember that personal style is exactly that: personal. The best way – no, the only way – to achieve a style that is truly your own is to do the things that others wouldn’t dare to do. History remembers the iconoclasts. Look at this man. See how the people turn their heads.

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