Let me guess…
You want to dress well, but you have no clue how to go about it.
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 a smart man, and you should be able to figure this out. You just have no clue where to start.
You have no clue what to focus on.
But you know what?
You’re Not the Only Guy Struggling to Figure Out How to Dress Himself Better
Many guys struggle with it.
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 tees to something more respectable, I had a hard time figuring out how to dress well.
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 fashion tips before I found the nuggets that actually worked, but eventually, I developed a much better dress sense. Just see for yourself:
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 do it 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, it 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
When you want to start dressing with style, you have to start from the beginning.
That doesn’t mean you should discard of all your clothes 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.
Saying goodbye to some of your favorites will be hard, but it must be done in order to make progress.
But don’t worry; you’ll get new favorites.
You’ll get 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, I would often read something that completely flipped my world upside down.
Things I deemed inconsequential 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, and you’ll be open to learn everything.
Rule #3: Focus on the Basics
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 alone will benefit you greatly. I always say it’s half the battle, but it’s more like three quarters, if not more.
Too many men shoot themselves in the foot by getting the basics wrong.
Don’t be one of them.
Rule #4: Build a Solid Wardrobe Foundation
Rebuilding your wardrobe starts with a solid foundation.
You need to collect versatile wardrobe staples that match well with almost anything — basic items like white shirts, dark blue jeans and grey sweaters.
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. (And after you’ve built your foundation, you can add more eye-catching clothes to your wardrobe, and you’ll always have items in your wardrobe to wear them with. )
Rule #5: Keep it Simple
You have to remember that you’re a man, and being extravagant isn’t necessary. You don’t need a lot of bells and whistles to look great.
You can just keep everything simple.
Leonardo DaVinci once said, “Simplicity is the ultimate sophistication.”
Keep this in mind when you’re putting your outfit together. Stop over-complicating things. Simple style is the best style for guys.
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:
Which do you think looks better?
The shirt on the right completely throws off my body’s proportions, making me look like I raided someone else’s closet.
Dressing well is all about the fit, guys.
Fit comes first.
If you only follow one rule 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 variety. You won’t need lots to have a great arsenal of stylish outfits. You’d be amazed at how few you really need.
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?
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.
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.
Layering lets you play around with the clothes you have, so you should learn how to do it properly.
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.
However, when you start out, developing your own style is vastly more important.
Once you figure out what image you want to portray, you can start adding trends that will work with that image.
Rule #11: Look Effortless, Not Botherless
A man shouldn’t look like he has spent hours meticulously orchestrating his outfit in front of a mirror.
Looking like you just grabbed some clothes out of your closet is a lot more effective. You want to look good 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..
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 try things you never would have thought to wear before.
Maybe you try wearing chinos instead of jeans or a jacket instead of a sweater. Maybe you can try business casual attire or even a suit. Maybe you can try changing your sneakers for desert boots, loafers or brogues.
You’d be amazed how good you could look in items that you previously thought “weren’t you.”
In this article by Jay from KinoWear, he tells you to try on anything and everything in a store.
“This one exercise of trying on anything and everything will teach you more about style than reading a thousand style articles.”
It’s good advice.
Rule #13: Learn to Love Colors
Most males don’t seem to like wearing 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.
Rule #14: Wear Colors Sparingly
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, since you probably don’t know how to match them yet.
Stick to just wearing one color at a time for now, and keep the rest neutral. Once you’re further educated you can start trying to combine them.
Want to master the art of color matching right away?
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 the new you, 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, 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 all the time.
Simply aim to look like a better dressed version of yourself.
Rule #18: Accept That it Will Take a While
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, 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.
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, 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
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.
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 better about yourself, 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?