A stylish outfit does not even need to look perfect, according to Guy. “Even the perfect pair of trousers will crumple when the wind blows,” he writes. Instead, he suggests dressing with sprezzatura, the Italian phrase that means “studied nonchalance”. The idea is that for an outfit to look good, it must look natural – and nothing adds that sense of effortlessness than putting on a good outfit and forgetting all about it.

According to some, a lean or athletic body can make anything look good, while those not blessed with certain proportions are left to the misfortune of looking wrong in everything. This was news to Guy, as someone who has spent more than 15 years on a menswear forum, where men of all body types and budgets learnt to dress phenomenally. Plus, there’s no shortage of lean, athletic men who dress badly (just look outside). He proposes a better way of thinking about how to dress for your body type.

Ever since the coat-and-tie look retreated from daily public life, men have wondered what they’re supposed to wear to look good. Business casual can sometimes feel flat and uninspired; certain modes of workwear can occasionally feel archaic. Gardening attire – battered chore coats, rumpled corduroy trousers, chambray shirts, sweatshirts with stretched collars and the occasional technical jacket – promises all the romance we appreciate about other aesthetics while looking perfectly at home in contemporary environments.

The debate between ready-made and custom tailoring has raged on for more than 100 years. In 1931, the editors of the industry trade journal Apparel Arts published an article on the value of handwork. The quality of a custom suit ultimately depends on the skill of the tailor who drafts it and on whether the two of you are, in the end, a good fit for each other. Some people require custom work because their proportions fall outside industry norms. But by statistical design, ready-to-wear is built to serve most bodies. For many men, thoughtful alterations will achieve nearly the same result – and with far less risk.

Back when men’s dress was governed by time, place and occasion, certain overcoats were made to be worn over dark worsted suits when men were doing business, while others were designed to be teamed with Shetland knits and tweed sport coats in the blustery countryside. Out of these emerged specific details, such as collars that could be turned up against the wind or pockets that could keep frigid hands warm. Design conventions today are not as strict, as designers mix and match details to create a new language. But through learning the history of certain overcoats, we can better understand how to style them – and which might be best for our lifestyle.

For thousands of years, the start of a new year has offered a symbolic blank slate – a chance to reflect, reset and recalibrate. For the style-minded, the dawn of the year offers not just an opportunity for self-improvement, but also a chance to rethink one’s wardrobe. Here, Guy proposes five style-focused resolutions to help usher in a new year with confidence.

We travel, in part, to claim our capacity for attention and wonder. Things that may seem banal at home can take on a poetic quality when abroad, such an arched doorway or a fig tree spilling over a crumbling wall. However, this mindset doesn’t come magically upon arrival; it begins with preparation. The right set of clothes won’t guarantee a meaningful trip, but they can help make space for one. If travel teaches us to see, then dressing for the journey is the first step toward knowing how to look.

Holiday shopping breeds its own little ecosystem of anxiety – a blend of performative cheer, desire to get the perfect gift and the nagging suspicion that other people are better at this than you. The festive season compresses time, crowds swell and we’re left holding our purchases like uncertain props. Consider, then, a few strategies that might make this annual ritual feel a bit less fraught.

When Goldman Sachs sent a memo to employees announcing they no longer needed to wear a coat and tie, the firm didn’t say what should take its place. Management merely advised staff to “dress in a manner that accords with the company’s and clients’ expectations” and to “exercise good judgment”. In other words: you figure it out. This has caused endless confusion. But fear not, there are some guidelines on how to return to the workplace in style.

For roughly a decade from 2002, menswear was dominated by prep, Americana and all things heritage, leaving many men feeling secure in the knowledge they were adhering to menswear rules deduced by style philosophers. Then Hedi Slimane’s SAINT LAURENT revived a rebel grunge aesthetic with high-fashion skinny jeans and, almost overnight, the heritage movement vanished. With the movement now feeling like ancient history, it has become fashionable to question whether style can ever be timeless. Read on for Guy’s take.

The cowboy comes and goes as a pop-cultural force, but his sartorial allure persists as a steady electrical current. What is it about the American West that makes it so compelling? Many workers today dream of being able to unshackle themselves from their desks and spend time outdoors. Westernwear hints at qualities we wish to see in ourselves – plus, the clothes look really good. Here are a few ways to incorporate it into your wardrobe.

If you look at images of how men dressed in the past, you may be tricked into thinking that men only wore dark blues, earthy browns and stoic greys, as those are the colours we mentally impose onto black-and-white images. While it’s true that, ever since the days of Beau Brummell, many Western men have relied on sober colour palettes, not all have been so dowdy and tame. So how does one incorporate colour into a wardrobe? Guy offers three ways.

A friend once succinctly summed up personal style as the point at which someone can see a pile of your clothes on the floor and instantly recognise them as belonging to you. True personal style is an extension of you – a visible representation of your identity, personality and place in culture. But developing this can be a long process that requires a lot of experimentation and self-reflection. After all, you are answering the difficult existentialist question, “Who am I?” You can make this process a little easier by keeping four things in mind.

According to Andy Sachs of the culture blog Deez Links, the internet has flattened culture, making aesthetic inspirations entirely too traceable. People have surrendered their sense of personal style in favour of safe, algorithm-dictated outfits and the accessibility of digital information has made everything mainstream. “Men’s fashion, rather than opening new doors for identities to try on, has instead become the defining identity,” Sachs argued. But Guy has a counterargument: there has never been a better time in menswear – and tomorrow will be better still.

Since at least 2010, menswear writers have been predicting something new will replace slim-fit silhouettes. Many years on, it’s hard not to notice something has changed. You don’t have to throw away your slim-fit clothes, but the dismantling of slim-fit hegemony means men have more options nowadays for how they get dressed. If you’re looking to experiment with a looser silhouette, here are five suggestions on how to do so without feeling like you’re a kid playing dress-up in his father’s clothes.

Building a wardrobe that you will love and wear for many years requires more than just being able to spot quality. It requires knowledge of self, confidence in one’s taste, and consideration of “emotional durability”. As much as you can, try to buy things that you think you’ll love wearing even in 10 years. Here are some suggestions on how to do that.

In 1992, Rick Miller and his team at Levi’s wrote an eight-page brochure titled A Guide To Casual Business Wear showing how men could swap their coat and tie for more casual but still professional-looking attire. Think knitted vests in place of sport jackets, plaid button-down shirts with mid-wash jeans and denim button-ups with pleated chinos. More than 30 years after that fateful brochure, business casual needs another reinvention. Here are five suggestions on how to do business casual better.

Some men are resigned to wearing clothes they don’t love because they think style is not for them. When it comes to dressing larger figures, the fashion press doesn’t provide much inspiration or guidance. And this industry is not known for being size-inclusive. But it is simply not true that size is an insurmountable barrier to dressing well. Dressing is a skill and, like any skill, it requires only knowledge and a willingness to make mistakes.

The coat-and-tie look has been dying a slow death since the end of WWII. After the Casual Friday movement of the 1990s and rise of tech bros in the early 2000s, the suit was all but dead, surviving only in the corners of finance, law, government, and television newscasting. This has posed a problem for men who love tailoring. But the easiest way to incorporate tailoring into your life is to simply do it.

To be well-dressed means dressing appropriately for a setting. To be stylish, however, means mastering the art of dress and injecting some personality into your choices. So, how does one dress originally?

The idea that our clothing choices carry certain connotations is not novel. But respectability in dress is a particularly sensitive issue because it touches on people’s virtues, morality, and character, often carrying the weight of who is “deserving” in society. Dressing “professionally” nowadays requires you to know your audience. The best advice anyone can give is to make an effort. When necessary, dress in ways that accord with people’s expectations of what it means to look trustworthy and respectable.