How to Dress Well: 20 Must-Follow Rules for Men

Let me guess…

You want to know how to dress well, but you have no clue where to start.

You never grew up with much interest in personal style, and you never developed a natural instinct for how you should dress. And even though you can find a ton of information online, it confuses and overwhelms you more than it helps you understand.

And it sucks, doesn’t it?

Because you’re smart, and you should be able to figure out how to be a well dressed man. You just have no clue what you should be focusing on.

But guess what?

You’re Not the Only Guy Who Struggles with Dressing Better

Many guys struggle with how to dress better.

In fact, just a few years back, I struggled as well.

I was a terrible dresser.

And when I decided to step up from hoodies and graphic t-shirts to something more respectable, I had a hard time figuring out the dress code for a casual evening or a formal event.

But despite all my early failures, I kept trying, and eventually, things started to click in my head. I had to try out lots of terrible men’s fashion tips before I found the nuggets that actually worked, but eventually, I developed a much better dress sense.

Yes, I finally knew how to dress well, men.

Just see for yourself:

Robert's style transformation

I created my personal style. This is not the work of a stylist.

I could feel ashamed of the many years spent dressed like a slob. But instead, I feel proud.

Because I had zero style sense. I had to learn how to be a well-dressed man. And when I consider where I came from and where I am now, I’m proud of how far I’ve come.

And any man can do what I did, no matter where they’re at now.

You can do it too.

And with some guidance, you can learn how to dress well as men — a lot quicker than I did.

How to Dress Well: The 20 Rules Every Beginner Should Follow

You can figure this out.

You can improve that dress sense of yours.

And once things start clicking in your head, men’s fashion will actually become easy. You just need a bit of guidance at first, so you’re focused on the right things.

So I took the most important lessons that I’ve learned over the years and put them into this article.

These are the guiding rules that all style rookies should follow.

Rule #1: Start From Scratch

empty hanger
Just imagine an empty wardrobe. What are you gonna fill it up with?

When you want to start dressing with style, you have to start from the beginning.

That doesn’t mean you should discard all of your clothes in your dressing room right away. (I’m fairly sure society frowns upon naked men going clothes shopping.)

But, you should accept that you will eventually get rid of most of your current wardrobe. You will trade it in for one that’s better suited and more refined, even if you still want to keep it casual.

For instance, swap your graphic t-shirts with casual t-shirts in solid colors.

Yes, saying goodbye to your favorite skinny jeans, brown blazer or baggy denim jacket will be hard when you do it the first time. But it must be done in order to make progress. 

Don’t worry though; you’ll get new favorites.

Better favorites that will make you look way more awesome.

Rule #2: Forget Everything You Think You Know

One of the hardest things I ever had to accept was that my fashion-knowledge was nonexistent.

During my researching stage on menswear, I would often read something that completely flipped my world upside down.

Things I deemed inconsequential in men’s clothing turned out to be of vital importance, while things that I thought were crucial turned out not to matter at all.

You should accept that you may not know as much as you think.

You should think of yourself as a complete beginner, so you don’t gloss over anything that could help you see the light. Otherwise, you’ll likely skip important lessons.

Assume you know nothing about men’s style, and you’ll be open to learning everything.

Rule #3: Focus on the Basics

Basic white tee
You Can’t Get More Basic Than a Plain White Tee

So now that you’ve forgotten everything you knew, what do you think you should focus on first?

The basics, of course.

Mastering the basics in clothing alone will benefit you greatly in your quest to be a stylish man.

I always say it’s half the battle, but it’s more like three quarters, if not more.

A white button-down oxford shirt under a navy blue tailored suit with dress shoes is a great business casual basic. If you want to look dapper in street style and casual wear, you could never go wrong with dark denim jeans and a white t-shirt.

Too many men shoot themselves in the foot by getting the basics wrong, like wearing your oxfords with skinny jeans.

Don’t be one of them.

When it comes to selecting a basic tailored suit, a classic style is dark colored, single-breasted, two-button that fits well across the shoulders.

Some basic styles in shirts include button-down oxford shirt, dress shirt, chambray shirt and poplin office shirt (works well for dressing business casual).

My point is: You don’t have to know how to tie a bow tie or how to mix and match different patterns when you’re just getting started. Focus on the basics first. Focus on things like fit, proportions and color coordination.

Check out my Men’s Style Guide to master the basics and avoid mistakes.

Rule #4: Build a Solid Wardrobe Foundation

Rebuilding your wardrobe starts with a solid foundation.

You need to collect versatile, high-quality wardrobe staples that match well with almost anything — basic items like white shirts, dark blue jeans and grey sweaters.

At the start of your style journey, you want to build a basic wardrobe with clothes in neutral colors of white, grey, black, khaki, or navy.

Clothing like these will serve as training wheels while you learn to get the basics right.

Items like these will serve as training wheels while you learn to get the basics right. They’ll also keep you safe from making mistakes when you don’t know how to match clothes yet.

After you’ve built your foundation, you can add more eye-catching clothes to your garment collection, and you’ll always have items in your wardrobe to wear them with.

Apart from clothes, the other basic wardrobe must-haves include brown leather loafers, a brown leather belt, and a solid timepiece. (Make sure your watch is the right size and depth relative to your wrist.)

Rule #5: Keep it Simple

You have to remember that you’re a modern man, and being extravagant isn’t necessary. You don’t need a lot of bells and whistles to look great. You must feel comfortable.

A white button-up shirt with navy blue dress pants and a simple jacket could be your casual dress code for any occasion.

You can just keep menswear simple. Even your underwear should be restricted to simple cotton boxer shorts or boxer briefs.

Leonardo DaVinci once said, “Simplicity is the ultimate sophistication.”

Keep this in mind when you’re putting your outfit together. Stop over-complicating things.

You don’t need to overdo it, and you don’t need to go from Homer Simpson straight to James Bond.

There’s no point in wearing a three-piece suit to a Star Wars or Game of Thrones marathon with friends. For most occasions, a down-to-earth casual look is fine. Your mission is simply to make casual look cool.

And you don’t have to be a creative genius to put a cool casual look together. You don’t have to wear 60 different items at a time, like guys you see in magazines sometimes. Just keep it simple.

A simple style is the best dress code for the modern gentleman with great style.

Rule #6: Fit Comes First

This is the golden rule; getting the fit right is your priority, always.

Unfortunately, most guys get this wrong, and getting this wrong sabotages anything else you try.

I mean, just compare these two shirts:

Shirt fit untucked
The difference between good and bad fit

The shirt on the right completely throws off my body’s proportions, making me look like I raided someone else’s closet. It may look comfortable, but the tailoring is terrible for my body shape (the sleeves are way too long and too much billowy fabric around my midsection).

When selecting your shirt style, it is crucial to nail your size. Ensure your shirt sleeves end where your wrist meets your hand, and your collar has a finger-width of space when fully fastened.

Dressing well is all about the right fit, guys.

Fit comes first.

If you only follow one of the men’s style tips from this article, follow this one.

Rule #7: Trim Your Wardrobe

Having a bulging wardrobe offers no benefit.

In fact, having lots of clothes in your wardrobe is impractical.  (Which is good news for guys who are trying to build a wardrobe on a budget!)

You want to keep your wardrobe trim.

Never fill your wardrobe up with lots and lots of clothes, thinking this will offer you a nice variety. You won’t need lots to have a great arsenal of perfectly fashionable and stylish outfits. You’d be amazed at how few polo shirts, dress shirts, socks or pair of jeans you really need in your casual wardrobe.

Moreover, if you buy fewer pieces, you can afford the best quality that fits your budget.

Also, you should prune your wardrobe periodically for items that look washed out, that no longer fit or that you simply no longer wear. You should discard these items and keep your wardrobe decluttered.

Rule #8: Expand Your Options

You don’t want to be that guy that wears the same outfit day in and day out. You need a bit of variety.

Does this seem paradoxical to you with the previous rule?

It shouldn’t.

You can trim your wardrobe and expand your wardrobe at the same time. You only need to ensure all your clothes can be worn together.

For instance, if you always wear your grey-and-red graphic tee with your wicked dark-red cardigan, swap it with wardrobe staples like a white shirt or a solid black tee. Now you have more than one outfit combination without having to buy new clothes.

Rule #9: Layer Up

Knowing how to layer clothes will give you ultimate use out of everything in your closet, and it will help you create more interesting outfits. For instance, you can layer your collared shirt with a crew neck pullover and a trench coat to look cool.

A penchant for layering lets you play around with the clothes you have, so you should learn how to do it properly.

Examples of casual layered outfits
Examples of casual layered outfits

Rule #10: Forget the Trends, Develop Your Style First

Many men think they have to be on top of all the latest trends to become more stylish.

The fads that are showcased at events like New York Fashion Week come and go. Most of the time, the “trendy” outfits they display on the runway will never suit the everyday guy — even if you’re an impeccably turned-out gentleman.

Therefore, when you start out, developing your own style is vastly more important.

As a general rule, dress your age.

Once you figure out what image you want to portray, you can start adding trends that will work with that image. Maybe monogrammed cuff links, a slim fit oxford shirt, or hey, maybe even bow ties?

Rule #11: Look Effortless, Not Botherless

With great style comes the great responsibility of looking effortlessly fashionable. A grown man shouldn’t look like he has spent hours meticulously orchestrating his outfit in front of a mirror.

Looking like you just grabbed some quality clothes out of your closet is a lot more effective. You want to look impeccable while looking like you’re not making an effort to look good.

But that doesn’t mean you should look like you didn’t bother. Your clothes must still look good on you, and they must work together in a way that’s pleasing to the eye.

And not just your clothes. Your hair, shoes, socks, and accessories like glasses,a leather belt, and wrist watch – everything should have a casual yet stylish look.

You still want to look like you know what you’re doing.

Rule #12: Try New Things

When you’re developing your sense of style, you want to open your mind to new types of clothing and clothing styles. You should be comfortable trying things you would never have thought of wearing before.

Maybe you try wearing chinos instead of jeans or a leather jacket instead of a sweater.

Maybe you can try business casual attire or even a suit instead of your usual casual clothes.

Maybe you can try changing your white sneakers for desert boots, loafers or suede Chelsea boots — or maybe even a pair of dress shoes.

You’d be amazed how dapper you could look in items that you previously thought “weren’t you.”

Whether it is casual attire or an outfit for a black tie event, you must learn to challenge yourself. You could even experiment with your hairstyles.

Trying on everything and anything will teach you more about your personal style than all the style and fashion blogs combined.

Rule #13: Learn to Love Colors (But Wear Them Sparingly)

Many males don’t seem to like wearing bright colors that much. Many of us stick to a basic color scheme of black, white, grey, and blue.

If that sounds like you, you want to expand your color horizons.

You have to figure out which colors work for you, and the best way to do this is to try them out. (See previous rule.)

Colors can make an outfit pop, so you should never shy away from them.

BUT!

While you should learn to love colors, you want to avoid wearing too many of them at the beginning of your style journey.

You’ll risk wearing incompatible colors or colors that don’t flatter your skin tone since you probably don’t know how to match them yet.

Stick to wearing one color at a time for now, and keep the rest neutral. Once you’re further educated, you can start trying to combine neutral colors with brighter shades.

two-piece-one-color outfits
Examples of outfits using one color with neutrals

Want to master the art of color matching right away?

Check out my color-matching guide for easy color-matching tricks.

Rule #14: Respect the Dress Code

A stylish man will always consider the dress code of the place or event that they’re going, and they will dress accordingly.

Depending on your lifestyle, you can probably go with a casual look for most occasions. If you’re just hanging out with friends, having a beer at your local pub, or going to a barbeque, you don’t need to show up in suit and tie.

On the other hand, if you work in an office, you’ll probably have to wear a suit at times (if not all the time).

If your friends are having a beach wedding, you should probably go for more casual wedding attire. You might leave your tie at home, and you could even come in open-toed shoes.

However, if they’re saying their vows in a church, this summer wedding attire will make you look like a fish out of water.

For most situations, you can probably figure it out. Just try and imagine the clothes all the other people will be wearing, and take it one step up. That way you’ll never be underdressed, but you’re safe from being too overdressed as well.

But when in doubt, just call ahead and ask.

Rule #15: Laugh Off the Jabs

When you start improving your style, you’re guaranteed to receive a few jabs from your friends.

The secret to dealing with this is not to care and laugh it off. Just crack a joke about it yourself. That way you’ll be in on the joke, instead of the butt of it.

Eventually, your friends will get used to your new dress code , and the jokes will cease.

Rule #16: Be Open to Feedback

You may also have people in your life that will genuinely try to help you in figuring out what to wear, so be open to their advice.

Consider the person the advice comes from and what they have to say.

Usually, you can tell when a criticism is genuine, or when someone is just trying to cut you down a few inches.

Hint: People who provide sincere counsel will usually be people that dress fairly well themselves.

You should also listen to the women in your life, as they often are happy to give their honest feedback (although they can also be too supportive).

Rule #17: Be Honest With Yourself

You never want to look like someone that you’re not. You’ll feel incongruent when you sport a look that doesn’t fit with your personality.

If you’re a an introvert, wearing extremely loud outfits will seem weird.

If you’re a laid-back type of guy, you may not want to walk around in formal suits with pocket squares all the time.

Simply aim to look like a better dressed version of yourself.

Rule #18: Accept That it Will Take a While

watch
Style reinvention takes time. There’s no rush.

Your sense of style is like Rome; It won’t be built in a day.

You’ ll need a while to fully grasp all the little intricacies that make an outfit great.

Personally, I spent years learning and experimenting before I could put everything together. It took me a long time to discover a look I was satisfied with and could wear with confidence, mostly because very little I tried actually helped me.

Don’t expect to become a better dresser within a month or two. You should prepare to spend some time on it.

Rule #19: Accept That You Will Make Mistakes

We all make mistakes. None of us are immune to this. I still make mistakes to this day.

Look at celebrities and popular style icons.

They often have personal stylists or designers creating clothes just for them to wear, and the clothes they wear are judged under a microscope.

They make mistakes in what they wear, but it’s because they try new things. Sometimes it works; sometimes it doesn’t.

This shouldn’t keep you from trying new clothes.

The road to success is paved with mistakes. You just need to realize when you’ve made one, accept it and move on.

Rule #20: Know That You’ll Get There Eventually

Robert's new style

If you keep working on it, eventually you’ll train your eye for style.

You’ll notice details in your own and other people’s outfits. You’ll know when something works and when it doesn’t. Selecting a great outfit from your closet will be as easy as riding a bike.

No matter how much you’re struggling, take comfort in the knowledge that you’ll get there eventually.

It’s Not Just Your Clothes

A smart man doesn’t just wear sharp clothes. He also knows how to look sharp and well groomed.

Men’s health is as important as their dress sense. Develop a simple yet effective grooming regime – clip your nails, comb your hair. Decide if facial hair is your style (this is where Rule#16 can come in handy).

Also, take care of your clothes and accessories to make them last longer. Take your suit to the dry cleaner often. Polish your shoes regularly. Use wooden hangers for your bespoke navy suit or expensive leather jacket, and a shoe tree for your shoes.

Follow These Rules and Develop Your Sense for Dressing Sharp

Following these 20 rules will help you build a kick-ass style, but you will have to work on it.

Change never comes from reading things; it comes from taking action.

So if you’re serious about taking your style to the next level, pick one small thing you want to improve, and work yourself up from there. (I recommend starting with #6)

Pick one thing, and then focus on mastering that one thing. Then, pick the next, and the next, and the next.

Slowly but surely, you’ll start to see major improvements. Slowly but surely, you’ll developed your sense of dressing well. Slowly but surely, you’ll create a look that kicks ass.

And then, you’ll notice that you feel comfortable about yourself and fashion, that you get more respect, and that you catch more attention from the ladies.

Because that’s what a kick-ass style will do for you.

And all you need to do is follow these rules, focus on on the right things, and take one small step at a time.

So let me ask you…

What small step will you take today?

Did You Find That Useful? Then Check This Out…

I wrote a men’s style guide that simplifies the art of dressing well, focuses on what matters, and takes you through it one step at a time. Enter your e-mail below and you’ll receive three free chapters, which will show you:

  • How to build an easy-to-match wardrobe
  • How to make shirts look awesome on you
  • How to create flattering clothing combinations

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