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How to Dress Well (6 Rules for Style All Men Should Follow)

6 min

Paying attention to your appearance can go a long way. By applying these six rules to your own life, you'll quickly see that being stylish is only a matter of making a few intentional decisions that can impact the kind of life you have and the people you meet.

I understand that learning to dress well is a tall order for some. I remember the days when clothes were just "clothes" to me. As long as they covered my body, were comfortable, and didn't make me look bigger than I was, I called them "good."

But whether we like it or not, what we wear says something about who we are and can directly impact our trajectory in life. This isn't a guarantee. You may very well be someone who found your way to achieving success for yourself, built wealth or fell in love without needing to invest much time, attention, and personal funds into constructing your wardrobe.

But paying attention to your appearance can go a long way. By applying these six rules to your own life, you'll quickly see that being stylish is only a matter of making a few intentional decisions that can impact the kind of life you have and the people you meet.

Here are my six rules for style that, if followed, can enhance your life for the better.

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Your clothes must fit you well, plain and simple, and this is one rule that I firmly believe will always stand the test of time.

Admittedly, I'm not a fan of specific trends such as the baggy or ultra-tight look (one being more popular than the other at the time of my writing this). Some people can pull these looks off, and depending on where you live and what is considered stylish in that area of the world, you may or may not find it easy to adopt particular looks for yourself.

When you're just starting to build your wardrobe (or looking to begin anew), the assumption is that you aren't quite sure what your style ought to even be.

Not everyone can pull particular looks off. Over time you will most likely determine if you can or can't rock a specific outfit, but for now, focus on selecting garments that fit you well so you can get on the right track.

No matter the era, timeless, well-fitting clothes will always look handsome on you, and if you make a point to work out and stay trim, this will only help you even more in the long run.

Regardless of how you feel about yourself in the clothes you wear, the fact remains that wearing ill-fitting garments does nothing to help your appearance (or build confidence).

Prioritize fit above everything else.


Finding a tailor will change the game for you. Simply put, a reliable and trustworthy tailor separates the boys from the men when dressing well.

Having a good tailor means taking items in your wardrobe that you were thinking about selling or donating and turning them into workhorse staples from which you can get a lot of wear.

A great tailor will save you money in the long run and, more importantly, help you to nail the fit of your clothes if you are the type of guy that doesn't have an "off-the-rack" build.

Having a great tailor is like maintaining a rewarding marriage; it requires trust and continual communication, so ensure that these are values that each of you can share.

If you aren't sure how to find a tailor you can trust, see my separate article here.


Colors matter. This aspect is a little more nuanced than making sure your clothes fit properly, but it helps create cohesion, which is commensurate with a well-put-together outfit.

For example, your skin's undertone plays into the colors you should choose when deciding what to wear. This matters because our objective should be to help guide a person's gaze towards our face, and we accomplish this by making intentional decisions with the colors of our outfits.

Understanding which colors complement each other is critical as well. Mix blue and green together for an analogous palette, which often results in some reasonably handsome outfit combinations (when done correctly).

And let's not forget the fact that each season of the year comes with its own set of preferred color palettes; for example, Spring and Summer months ought to include brighter and more vibrant colors, while the Fall and Winter seasons incorporate more neutral colors and darker tones to reflect the often colder, bleak weather.

It may seem inconsequential, but the understanding of color makes a difference.

Great style lasts forever. I will talk about developing your style in separate posts, but that doesn't mean you should follow through with pairing neon tracksuit pants and a leather jacket to call the look you've created "edgy."

The truth is, there are right and wrong ways to dress. I understand if you like the baggy trend, but this can be dangerous territory for style newcomers, and quite frankly, it looks sloppy if your clothes don't fit you well (in most circumstances).

I will work hard to help you understand the concept of "timeless style." Adopting this doesn't make you generic; instead, it allows you to appear more refined.

Stacking rings on every finger is just as tackey today as it ever was and will ever be. Adding overly loud pops of color and calling them "statement pieces" doesn't do anything for you, so best to break those habits now.

Buying into these trends takes too much of your mental focus away from what matters, looking good (not too loud), and having confidence; it also slowly murders your wallet in the long run because trends continuously come and go like the wind.

Worse, you put more pressure on yourself to dress well, which is never good. Style should enhance your life for the better, not create more undue stress.

Take this with a grain of salt, of course. Perhaps you already know yourself to be someone who immensely enjoys keeping up with trends, and that's perfectly fine. You've accepted your desire to be a fashionista, and you will likely look great in the trendy pieces you wear.

For average guys, though, I recommend following Rule #4 to the letter.


Here is some "tough love" for you. Get into shape. You can have the best clothes made from the best materials, all from the best crafters, but if your body makes those garment's jobs difficult, you've managed to force something that was meant to work for you to work against you.

Getting in shape isn't as hard as you think. Take control of your life and find ways that work for you.

Need to lose weight but don't understand how it works?

It isn't as difficult as you think to build a body that helps you feel free, confident, and, more importantly, like the man you know yourself to be.

I can't stress enough the importance of physical self-care; it isn't just about looking lean and sexy; it's about improving your health to become the best version of yourself; having a body that your clothes can flatter also helps with this.

I know it can be difficult when just beginning, but I have your back and can help you along the way.

Staying physically healthy is something we should all do for ourselves, first and foremost, because we are worth it.  


This rule is, ultimately, just as it sounds. Try not to overdress or underdress; just dress for the occasion. A gentleman must know the event and always select the outfit that best suits it.

Another way of interpreting this rule is to have a wardrobe that facilitates numerous options. You'll find yourself being a part of all kinds of occasions, so ensuring that your wardrobe is interchangeable is crucial to fulfilling this rule.


Take pleasure in knowing that you have things under control in your life. This is synonymous with being a gentleman. You don't have to try and get everything right all the time, but arm yourself with the knowledge to control what you know you can and remember that even though dressing well isn't everything, it indeed says something about who you are.

So show the world that you are proud to be who you are. Apply these rules to your own life and watch as others take notice.  


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