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.
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.
These are the guiding rules that all style rookies should follow.
Just imagine an empty wardrobe. What are you gonna fill it up with?
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 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.
You Can’t Get More Basic Than a Plain White Tee
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 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.
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:
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?
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.
Layering will help you create more interesting outfits
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.
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?