Getting dressed is about telling a story every time you leave the house. What’s yours?

Life is full of learning. We learn how to read, write, count, run and even eat. But one learning is forgotten too often and men have been suffering from it for a long time: how to dress? I will immediately clarify: everyone “knows” how to dress, that goes without saying. I assume that everyone reading this is aware of putting on a shirt, pants, shoes and underwear when they leave the house. It’s from a completely different angle: who can boast that they really know how to dress when it comes to a shirt and jacket? Not many people. Very few people, in fact.

Asian man wearing a grey checkered suit
Dressing well can often seem out of reach, but is it as complicated as it seems?

However, these are very simple basics that can be learned in a flash. We’re not talking about becoming a dandy here; just knowing the basics of how to put together the different pieces that make up an outfit to get the most out of our clothing pieces. It’s as simple as that. What shirts should I get? Do I have to buy six suits for my job? What should I match my tie with? After reading this article, you will be more knowledgeable on the subject and will make much more informed decisions in the future.

Do I consider myself a style expert? Of course not. That’s why I sat down with Charles Desnoyers, stylist at Montreal’s Surmesur boutique, to learn more about the basics of this often forgotten aspect of our lives.

But where to start?

At the thrift store! For the novice who is starting from almost zero for his wardrobe, thrift stores are the ideal place to find the basic components of a successful style. You can find great pieces at very low prices. Some items don’t have to fit perfectly, like jackets, for example. A quick trip to the tailor to make a few alterations, and you’ll have a garment that looks great for a fraction of the price.

For your first two outfits: navy and gray. You can never go wrong with these colours: in addition to being quite simple and classic, they complement each other perfectly, which means you can put them together and expand your number of outfits without spending more.

Two men wearing navy suits walking in the street
The navy suit is versatile and timeless, with good reason!

Which shirts to buy?

It’s all well and good to buy shirts, but which ones? There are as many to choose from as there are Canadiens jerseys the day after a loss. Charles makes it simple: blue, white, lilac/pink. That’s it—no need for anything else. The reason is simple: these colours go with everything, are super classic and can be worn for any occasion. You can never have too many!

If you wish, you can still opt for patterns, but keep it simple rather than extravagant. However, before you go down that road, make sure you have the basic variations: plain, striped, plaid, light, dark, etc.

At this point, you can start exploring funkier colours like teal, yellow or orange, but always start with the same trio: blue, white, lilac.

A blue, white and lilac dress shirts
Blue, white, and lilac, those are the basics!

Who should I listen to?

Charles is very clear on this point: follow the advice of your stylist! That’s his profession: his advice is well thought out and comes from years of experience. Listen to your stylist the same way you listen to your trainer or nutritionist; they literally get paid for it! Even if your girlfriend “has a good eye” or “thinks it looks good on you,” it never equals the expertise of an experienced stylist.

Basic tips

Style is something that can be learned without necessarily becoming an avid fashionista. It never hurts to be aware of your clothing and know how to choose the right colours, textures and materials.

To advise someone new to building their wardrobe, he surprised me with his answer. The first investment to make is a good pair of shoes. You shouldn’t be afraid to spend $400 or $500 on a pair. The reason? Your feet won’t change, but as your career progresses, the rest of your body will.

If we persist in staying with pairs of shoes at 50-60$, the purchase becomes almost annual due to the lower quality of materials, and we quickly catch up with the price of quality shoes that will last us a decade or even fifteen years.

Stylist advice: learn how to iron your shirts!

Charles couldn’t be more explicit about this: learn how to iron your shirts! There are many tutorials on YouTube, and after that, it’s good for life! You don’t have to iron your entire wardrobe on a Sunday afternoon either: you can do it only for the shirt you’re going to wear during the day. Making ironing part of your morning routine, just like shaving or showering, is a simple way to take care of your style without overwhelming yourself. 

According to him, there is something very masculine in this; the desire to look good, to detach oneself from the image of the man who doesn’t care about his clothes. He takes care of his own shirts, chooses his socks, ties, handkerchiefs, etc. In his opinion, this is part of the famous sartorial quest, without falling into caricature or dandyism. In the same way that we take the time to choose our car and take care of it for years, our clothes should receive the same treatment.

It’s okay if you only want to wear navy suits or want to explore colours like pink; you have to be comfortable with what you have and not be afraid to dare to wear what you want, to try new things. 

A white shirt on an ironing board
Ironing is a simple task that every man should master.

What’s next?

After navy and gray, the stylist will recommend checks, again in the same colours. According to Charles, if the workplace allows it and the client wants it, checks on a brown suit is an underrated style. 

What about black? It’s hardly ever worn anymore. It’s very, very classic. It looks like you’re going to a funeral or a ball. Those who want to explore other patterns for their next outfit, lined, commonly known as pinstripe, are coming back into style.

Now that you have some outfits, you can do some mix-and-match! Blue and grey go perfectly together, so we can combine our grey jacket with our blue pants, and vice versa. Then we can play with beiges and browns. For example, a brown jacket with gray pants is a great combination that we, unfortunately, don’t see often enough. 

What should we remember? Don’t buy more; buy smarter! 99% of men need a maximum of 10 shirts and three pairs of shoes: one black, one oxblood and one brown, that’s it! With this, your style is guaranteed for years to come without becoming redundant.

If I want to go even further?

This step is optional but can suit the modern gentleman who has found a new passion for the sartorial art: dressing according to the seasons. 

One misconception about summer is that you should be dressed as little as possible as soon as it gets hot: this is not true! With a good thin wool or linen suit with a cotton shirt, you won’t be warmer than in a t-shirt. Don’t be afraid to play with materials! Same thing for colours: you can try brighter colours.

Two men wearing a white and a yellow suit with sunglasses
To take your style to another level, you can try less traditional colours like white or yellow!

In the winter, thicker materials like flannel are preferable. You’ll be much more comfortable than with your thin summer suit once January arrives. You should prefer duller and more discreet colours versus bright colours or beige when it comes to colours. 

Charles adds this: “It’s weird that in Quebec, it’s freezing in the winter and very hot in the summer, but we dress the same all year round with our suits.”

No matter how involved you are in your wardrobe, one last tip: avoid polyester and anything unnatural!

When can we incorporate custom-made products?

Let’s say it right away: custom-made products are an investment. We can’t say it enough. Yes, it’s more expensive. But if you work in an environment where you often have to wear suits, several reasons can convince you.

First of all, generally speaking, people dress badly. That may sound raw, but hey, this comes from someone who has been dressing men for almost 15 years! Having a well-fitting suit makes you look your best instantly, and others notice. It’s hard to explain, but you feel it: you seem more in control, you look better.

Secondly, it’s an investment matter: am I willing to put $1000 on a suit? Well, just like that, probably not. For an outfit that fits me perfectly, that will last me for years, making me look my best in front of my colleagues and clients, and that is as comfortable as my Sunday morning pyjamas? Of course.

I have to wear suits all week, and I only have one navy and one grey suit, should I buy more?

No! The first step before buying another suit is to expand your shirt collection. It is certain that if you always wear a white shirt, you will always look the same, but if you wear a blue-lined shirt one day, a plain blue shirt the next day and a lilac shirt the day after that, you will never give the impression that you are dressed the same, even if you only have two suits. 

Speaking of owning no more than two or three suits, what happens to washing them? Do we end up wearing a dirty suit every other day? Of course not! Materials like wool are antibacterial, so there’s no need to take it to the cleaner every time. Same thing for shirts: simply iron or vaporize them and they will stay beautiful for a long time before needing to be cleaned. Sending such clothes to the cleaner too often will only damage them prematurely. Once a year is enough for most of them.

We also too often underestimate the importance of accessories. They are part of the components that take our outfit to another level. Whether it’s the watch, the socks, the tie or the handkerchief, they should not be neglected. 

Charles Desnoyers wearing three different suits
Mixing and matching your garments is a great way to diversify your wardrobe without buying more, as demonstrated by Charles himself!

Socks, tie and handkerchief? What do I do with this?

First and foremost: don’t buy them in a kit! The first step is to buy the accessories you think are good-looking; you can never go wrong with that! To find them, simply go to thrift stores, as mentioned before. You can find beautiful accessories for very low prices, and even from well-known brands!

Here are some basic rules for accessories so you can see a little more clearly before making bad purchases:

The handkerchief, if you decide to wear it, must match your shirt, nothing else! Too often, we see people trying to match it with the tie, which is a mistake. For example, if your shirt is plain, a handkerchief in the same colour but with patterns is a good way to go. Again, it’s not about rules set in stone: dare to explore with what drives you the most!

When it comes to ties, get a few lined ones, a few floral ones and a few plain ones. No more checkered or Snoopy ties! Colours like red, orange or blue are good starting points.

Finally, for socks, favour solid colours before patterns. Get pairs of socks in all sorts of different colours that will complement your ties. Too often we see people trying to stand out with funky socks versus their suit: these are not the socks that take a suit to the next level. Stylist tip: only solid colours! Gone are the days where the cool thing about your outfit is your socks.

That’s a lot of information? If you have one thing to remember about accessories, it’s this:

Infogrpahics of how to match accessories
Accessories should complement each other if you plan on wearing any.

That’s it! By matching your accessories in this manner, you’re on the right track when it comes to the look and effectiveness of your outfit. Of course, the world of fashion is extremely vast, and there is a myriad of ways to match your clothing pieces, but this is a good starting point for the uninitiated!

If you want to take your style to the next level, nothing beats consulting with one of our stylists at Surmesur!


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