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How to Dress Well (6 Rules for Style)

10 min

Paying attention to your appearance can go a long way. Here are my six rules for style that I think all men should follow.

OUR PERSONAL STYLE MATTERS

If you're seeking advice on dressing well, you've come to the right place. No trends, no fads, and no nonsense. I understand that learning to dress well can be a challenge for some. I remember 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."

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 find success, build wealth, or fall in love without investing much time, attention, and personal funds into constructing your wardrobe. Paying attention to your appearance can go a long way, though.

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.

This article aims to teach you how to dress well and better determine your style, so you can feel confident about yourself.

Being a true gentleman involves choosing well-fitting clothes for different occasions that complement your body type while adding tasteful, personal touches to let your personality shine through.

Read here for my complete guide to being a modern gentleman.

FINDING YOUR OWN PERSONAL STYLE

A gentleman makes the most of what he's got and invests in timeless classics, such as quality neutral-colored basics that can be mixed and matched with other garments in a classic and highly interchangeable wardrobe. We can achieve this by eliminating flashy clothing, prioritizing brilliance in the basics, and investing in clothes that will remain stylish decades into the future.

If you need help building a starter capsule wardrobe that can cover you for virtually any situation, check out this article here.

Dressing well shouldn't necessarily define you, but it should be a significant part of defining your image in the workplace and among your peers.

COMPETENCE BUILDS CONFIDENCE

Labor Vincit

When I was learning to pilot ships for the U.S. Navy, I realized that confidence was crucial for maintaining composure while working with a team of people to navigate our vessel through sometimes treacherous waters.

The key to building confidence is to work diligently to become competent. As we gain new skills and master them, a chain reaction occurs. This enables us to develop the skills needed to get things done, whether it's performing specific tasks or simply looking put together.

Be cautious of arrogance, though. Every modern gentleman should understand that confidence can quickly turn into arrogance if he isn't careful, which is never appealing.

Confidence means moving and walking with purpose and poise. It means standing up straight (not slouching your shoulders), wearing flattering clothes, shaking someone's hand firmly, and reading the room to behave appropriately. Ahead of anything, it's achieving all of this while being respectful.

Here are my six rules for personal style, which, if followed, can enhance your life and help you build confidence.

RULE #1: MIND THE FIT

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 be.

Each of us has different body types, so not everyone can pull off the same looks. As time goes on, you will likely figure out which outfits work for you and which don't. For now, concentrate on choosing clothes that fit you well to set yourself on the right path.

Choose clothes that compliment your body type because, regardless of how you feel about yourself in the clothes you wear, wearing ill-fitting garments does nothing to improve your appearance (or build confidence). Trust me.

No matter the era, timeless clothing that fits you will always look handsome. If you make a point to work out and stay trim, this will only enhance your style and confidence in the long run.

GENERAL RULES FOR PROPER FIT & SIZING

Remember, your jeans, chinos, and dress pants should never be too tight; they should be worn comfortably high on the waist. Shirts should also not be too tight. Your clothes should not hang off you excessively. Always remember that you are wearing the clothes; they shouldn't be wearing you! Prioritize fit above everything else.

RULE #2: FIND A TAILOR

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 who 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 each of you shares these values.

If you aren't sure how to find a trustworthy tailor, see my five-step guide here.

ELEVATE YOUR STYLE TO NEW HEIGHTS

A good tailor who knows what s/he is doing can explain which alterations are possible and which ones are not. Here are some examples:

These are just a few talking points that well-trained tailors should be able to speak through or even demonstrate, depending on your particular needs.

RULE #3: LEARN YOUR COLORS

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

PRIORITIZE NEUTRAL COLORS

Dressing well shouldn't be overly complicated or insanely expensive. By learning to work smarter, any man can "fool-proof" his wardrobe by choosing neutral-colored pieces that pair well with other neutral garments. The straightforward nature of a neutral-colored collection allows men to accomplish more with less by affording them virtually endless options.

Read here for why I think a neutral color palette is the best and easiest way to start dressing stylishly.

CONSIDER YOUR COMPLEXION

Your skin's undertone should also influence your chosen colors when deciding what to wear. This matters because our objective should be to help guide a person's gaze toward our face, and we accomplish this by making intentional decisions about the colors of our outfits.

I have written a separate guide for this topic, which you can read here.

I firmly believe that neutral colors are still a very safe bet for any and every man, regardless of skin tone. However, this does not change the fact that wearing the right colors to complement your complexion can be a powerful way to enhance your overall look.

Understanding which colors complement each other is also critical. Combining blue and green for an analogous palette often produces reasonably handsome outfit combinations (when done correctly).

Blue & Green sit next to each other on the Color Wheel (Analogous Color Palette)
If you aren't sure what analogous means or want to learn more about basic color theory, see my article here for a beginner's guide.

Let's not forget that each season has its preferred color palette; for example, spring and summer often 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 insignificant, but the understanding of color makes a difference.

GREAT STYLE LASTS FOREVER

Just because you can pair neon tracksuit pants and a leather jacket doesn't mean you should.

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).

Despite what others might say, adopting a more classic style doesn't make you generic; I think it makes you appear more masculine and refined. The modern era brings a bevy of "interesting" style trends, which I think we should remain cautious about.

For example, stacking rings on every finger is just as tacky today as it will be decades from now. Adding overly loud "pops" of color and calling them "statement pieces" doesn't help, so it's best to break those habits now unless you're actively trying to look like a kid playing dress-up (which I wouldn't recommend).

Buying into these trends takes too much of your mental focus away from what matters, which is 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, not create 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. The choice is yours.

For those just starting to take an interest in their appearance, though, do yourself (and your wallet) a favor and ditch the trends!

USE TASTEFUL ACCESSORIES

In my opinion, buying into trends isn't the best way to express yourself. Instead, I think including tasteful accessories such as quality neckties, tie clips, wristwatches, classic hats, and sunglasses can all be used effectively to create stylish and gentlemanly outfits.

We should select accessories that don't distract others by drawing unnecessary attention. Instead, our clothing choices should prioritize comfort while reflecting our style to the world.

Integrating the right accessories into our existing wardrobe allows our personality to shine, enabling us to express ourselves in a tasteful manner.

RULE #5: GET IN SHAPE

Here is some "tough love" for you. Get in 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 meant to work for you to now work against you. If you look good, then you feel good, plain and simple.

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

Want some workout ideas that you can do from the comfort of your home? Check out my workout playlists here.

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

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.

Starting can be daunting, but I have your back and can help you. Staying physically healthy is something we should all do because our bodies are temples and a gift from God.

See my separate article here for how to start a personal fitness routine.

RULE #6: DRESS FOR THE OCCASION

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

Dressing well isn't just about looking cool, and it certainly isn't about wearing baseball hats cocked slightly to the side. A gentleman understands the importance of adhering to appropriate dress codes; this means wearing formal wear at formal venues and business casual clothes at events that warrant such a dress code. A gentleman makes every effort never to appear slightly overdressed or underdressed; he simply dresses well for every occasion.

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

ALL THE DIFFERENCE IN THE WORLD

Trends come and go like the wind, but good style is timeless and lasts forever. Dressing well can make a huge difference in your appearance, allowing you to feel good and enabling your personality to shine through. Choosing the right outfit for an event is synonymous with being a gentleman.

You don't have to get everything right all the time but equip yourself with the knowledge to make a good impression no matter where you are. Remember that even though dressing well isn't everything, it says something about who you are. Apply these rules to your own life and watch as others take notice.

"For the Lord will be your confidence and will keep your foot from being caught." - Proverbs 3:26

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