“The Clothes are great, but it’s about the posture and attitude.”

 – Scott Schuman, The Sartorialist

The most important rule in all of style is to carry and dress yourself in confidence. In all things you do and in any path you choose to take, do so confidently. Have the confidence to make your own way, to achieve your goals and to look your very best every day. We all know that there is an undeniable attractiveness to someone who walks, talks and dresses with the utmost self-assurance. And on the flip side, there is nothing more noticeable than a guy who looks like he’s trying too hard while looking incredibly uncertain about himself.

The confident man wears his clothes with an ease that makes his striking pieces look like an everyday staple of his wardrobe. He owns his look, no matter what he decides to wear because it’s an authentic expression of his personality and character. On the other hand, the guy who is insecure about his appearance will be noticeably self-conscious of his clothing – touching it, fixing it up, looking himself up and down every reflective surface on the street. He’s not wearing his clothes, his clothes are wearing him.

So how can you achieve that confident style that some seem to just be born with? Well, that’s the thing – you don’t have to be born with confidence to have it. In this article, we’ll explore confidence in the context of style by exploring what we believe to be its three essentials characteristics.

1. Authenticity 

“Style is an expression of individualism mixed with charisma.
Fashion is something that comes after style.”
– John Fairchild  (Founder of W Magazine) 

Confidence in your style starts with an authentic expression of yourself. Have you ever tried to pull off a look you saw somewhere only to feel extremely self-conscious about it all day, constantly bothered by that uneasiness of looking silly?  If your image is inconsistent with who you are, this insecurity is a common symptom.

There are two types of insecurities: 1) you’re stepping out of your comfort zone to dress better and you’re getting used to your new self; 2) you’re wearing something that isn’t consistent with who you are as a person. The former is okay but the latter is not. At face value, this may sound complicated, but allow us to explain.

Example #1: You’re a gentleman who likes and wears suits on a regular basis but has decided to drop the “poppa-hand-me-down” sack suit in favor of a form-fitting, slimmer suit. You know this looks better, but you’re adjusting to an improved look. This is normal as there’s always a bit of “uncertainty” here. Ignore the uncertainty and be confident in your upgrade.

Example #2: You’re a gentleman who likes and wears suits on a regular basis but one day, liking the way a street-style blogger looked in a snap back hat, graphic t-shirt, ripped up jeans and high-top chucks, you decide to do the same. Now, you can’t stop fixing yourself, averting glances and wondering what people think of you.

Don’t get us wrong. There’s nothing wrong with experimenting with a new look, but it makes sense to transition and explore rather than jump in head first. So a good place to start is to get some clarity about yourself and what you intend to communicate with your image. If you’re a preppy guy who likes some street style, be a preppy guy with splashes of street style rather than a preppy guy uncomfortably trapped in street style.


2.  Confidently Take Risks 

Photography by Tommy Ton 

A stylishly confident guy isn’t afraid to try new things. So if you choose to express yourself with a preppy look, that’s fine, but why not experiment a bit? Being confident means being comfortable, but don’t be comfortable to a point of stagnation, be comfortable to the point of taking some risks. So take some chances, even if they are small. At the end of the day, your confidence should always trump your fears.

Here’s a quick and simple exercise to help build some stylish confidence: Write the following down on a piece of paper, “I can’t wear that, it’s just not me”. Scribble, cross, X or black-line the sh*t out of that same sentence. Now take that piece of paper, crumple it up or torch it (just don’t set your office or apartment on fire).

Stylishly confident men never let such language thwart their sartorial progress. Just because the entirety of a certain look or aesthetic might not be “you” doesn’t mean you can’t incorporate specific elements of that certain aesthetic to make it yours. You might be a guy who prefers a bacon cheeseburger over a grilled chicken salad, but that doesn’t mean you can’t enjoy that bacon cheeseburger with some lettuce and tomatoes and that also doesn’t mean you can’t enjoy a grilled chicken sandwich with some bacon and cheese. You’re a preppy guy who doesn’t like the whole rock-star-leather-jacket-skinny-jeans look? No problem, but why not try wearing a leather jacket with a button down, vest, tie and some slim denim? Be confident enough to take some risks and you’ll see how far you can go.


3. Not Giving a F*** (NGAF)

This is final and most important rule of being truly confident in style. But it’s the final rule for a reason. If it were the first rule, some guys would have stopped reading by now, canceled their upcoming haircut appointments, thrown out their razors and dug up those beer-stained jeans and fraternity t-shirts. So, NGAF needs to be taken in the proper context. By being confident in your style, NGAF means that your style is not dependent on the approval of others. It also means that you know you look good because you’ve taken the time to figure out how to authentically express your style, take some risks and hone your look to where it is now. More importantly, you understand that at the end of the day, style is a PERSONAL statement, one that should be yours and only yours – this is never at the mercy of trends, passing fads and the opinion of others. NGAF means that you dress for yourself because you know your style is an the extension of yourself and you’re fully confident in showing the world who you are.

There is a magnetic quality to the man who is confident about who he is and how he looks. He defines his clothes rather than let his clothes define him. He creates unique and original outfits that seem like an organic outflow of his personality. This may be you. If it’s not, it can be you. It’s the combination of authentic expression, risk-taking and irreverence that culminates into the stuff of icons—the Karl Lagerfelds, Lapo Elkanns, Steve McQueens of the world. Now it’s your turn. Go forth in confidence!