A famous Italian chef once said: “If you are not cooking with passion and love, then you are not cooking – you are just making something to eat”. I’m starting with this analogy because dressing, just like cooking, can be a form of art. An art that is mastered by those gentlemen that have well understood that building up a wardrobe takes a certain dedication and appreciation of classic menswear principles.

More importantly, besides naturally enjoying it, those gentlemen firmly believe that dressing appropriately is form of respect towards life and beauty. And while a charm à la Cary Grant or à la Gianni Agnelli may be innate, every gentleman can reach these elegance and sartorial heights with the right tools and knowledge. If you are keen to embark in this journey, this guide is for you.

Before we start it is crucial to debunk two myths that I’m sure you also encountered many times on a number of menswear blogs and papers.

First, matching colors comes only after matching fabrics (and choosing the appropriate ones for the occasion). Someone who knows how to dress would look perfect even in a very unusual color combination while pairing the wrong fabrics would 99.99% of the times result in an outfit that is unpleasant to the eye. In this case there are primarily two features to consider: the material of the fabrics and the weights. When in doubt, always opt for jacket and trousers of the same or similar weights. At the same time, animal fabrics such as wools are better paired with other wools and the same applies for vegetal fabrics such as cotton or linen.

The second myth is that classic menswear is full of “rules” that you must adhere to. Here you will never find the word “rule” as it falsely depicts what classic menswear is about. There are no rules in fact, only guiding principles and key concepts every gentleman should know to master the art of dressing well, feeling comfortable in your clothes and successfully building a wardrobe.

On guiding principles, there are a few common ones that must be highlighted. First, a gentlemen wardrobe shall be divided into four “registries”, as first skillfully described by Italy’s Cavalleresco Ordine:

• Formal: garments that we mostly need in our professional life, where the dress code is essentially determined by our job and office.
• Informal: garments that we enjoy in our free time, for example when we go to our favorite bar with a dear friend.
• Casual: garments that we also wear in our free time but for occasions that require a lower degree of formality or a more sportive look, such as a walk in the countryside.
• Ceremonial: garments that we need to attend a ceremony such as for example a wedding or the opera.

Now that we have described our playing field, there are two key questions we need to ask ourselves in order to put the above into fruition.

What is the context we are in?

Take a banker going to his office on Wall Street, a doctor visiting a patient in Naples, and a CEO of a manufacturing business meeting clients in Los Angeles. Technically, all these occasions belong to the formal registry. However, the banker in this example would look great in a three-piece pinstripe suit in gray or blue, giving him a highly formal and business-oriented look perfectly appropriate for the streets of New York City and for the deal that he is about to close.

The very same suit would not look as good on the doctor in this specific example because he would most likely prefer a less-formal suit, perhaps because he needs to take off the jacket at some point to perform the visit or because he would want to appear more friendly and relaxed to his patients.

The context we are in is not only determined by our occupation and work environment but also by the connotations of a place or a city. Specifically, a gentleman living next to the sea can allow himself to wear brighter fabrics and colors that would otherwise look excessive and out of context in a big city center surrounded by skyscrapers. The opposite is also true.

What is the message we want to deliver?

To dress is a language and our garments are the words we can use. More often than not, in fact, what we wear can superbly complement and support what we say verbally. Sometimes even allowing us to express ourselves without the need of speaking, as long as what we want to convey is true.

The aforementioned three-piece pinstripe suit would perfectly serve a lawyer whose objective is to transmit confidence and trustworthiness to his clients and counterparties. A Scottish Tweed sport jacket would look phenomenal on someone who loves the countryside and find himself the happiest when walking in the nature.

At a cocktail party, a single man in his 30s might want to opt for a tuxedo that is cut more open on the front and on the fitter side because he might want to socialize and make friends while a married man in his 50s might go for a more rigorous tuxedo because, perhaps, he doesn’t love to dance or because he feels it better fit with his body and social status. As you can see, the list of examples could go on forever.