9 Secrets for Dressing Well: A Roadmap for the Style Rookie

Editor’s note: This is a guest post from Robert van Tongeren.

Some men make it look so easy, don’t they?

They seem to have a natural sense of what looks good on them and what doesn’t. But for you, the learning curve seems ever so steep.

You want to look your best, but you feel clueless about fashion and style, and nothing you try seems to fall together right.

Well, it’s not all your fault.

You were taught how to dress yourself when you were young, but I bet you were never taught how to dress well. Nobody ever taught you what makes an outfit work and what doesn’t. And now you’ve grown up with numerous bad style habits and misconceptions about how you should dress.

And you know what makes it worse?

The Internet will only confuse you more because it’s littered with misinformation, trivial fluff, and half-truths.

But don’t worry.

Today you’ll discover a few secrets that will clear some things up for you. These secrets will show you what works and what matters, and with them you’ll have a much easier time making sense of style.

And eventually you’ll be one of those men who make it look easy.

1. Dressing Up Isn’t the Same as Dressing Well

Too many men still believe dressing well is achieved by wearing dressier clothes. They believe wearing a suit, or a jacket, or — in some cases — a mere buttoned shirt will take their style up a notch.

These men only end up making the same mistakes, except on dressier (and often, more expensive) clothes. But in the end, they barely look any better.

Other men are crippled by this assumption. They change nothing at all because they’re uncomfortable with the idea of abandoning their casual look.

But take a look at what you’re wearing right now. I guarantee you can make it look better than you make it look now, even if you’re just wearing your everyday pair of jeans and a T-shirt.

Maybe you can get them in a better fit, or maybe a different color will look better on you. Maybe you’re wearing a “funny” tee and you can trade it for something more mature.

If you’re not ready to step too far outside your comfort zone, it’s fine to start with what you know. A well-chosen pair of jeans and T-shirt will still look better than a poorly-chosen suit.

2. One Item That Fits is Worth Ten That Don’t

Clothes that fit properly are nearly impossible to find off the rack — especially shirts and jackets. Yet the fit of your clothes largely determines whether they make you look sharp or sloppy.

However, even men who know the importance of fit often refuse to invest in a tailor. They’d rather spend their money on additional clothes than on adjustments to make the clothes they have fit perfectly.

But isn’t it better to have a few shirts that make you look sharp rather than dozens that make you look sloppy? If so, having your clothes adjusted as needed is a better investment than just buying more and more clothes.

Just try it with one shirt and you’ll see what a difference it makes.

3. Avoiding Colors Can Make Dressing Well Easier

To make an outfit look good, you have to balance a lot of factors, which can be hard for a rookie. You have a lot to keep in mind.

But you don’t need to learn it all at once.

The most effective way to learn any skill is through focused practice and steady advancement. And just like any other skill, you can learn how to dress better by taking it one step at a time. All you need to do is set constraints.

For example, many men struggle with matching colors, but you can postpone that struggle by only allowing yourself to wear one item of color at a time and keeping the rest neutral (i.e., white, grey, or khaki). This way, you can focus on other factors without having to worry about matching the wrong colors.

In fact, you could completely avoid colors, patterns, or any strong textures at first and focus fully on getting the fit and proportions right. Then you can loosen the reins one step at a time, allowing yourself to wear one color, then one pattern, then two colors, etc.

The more constraints you set, the easier it becomes. (And if you’re worried about looking bland, know that I often get the most compliments on my simplest outfits.)

4. Being Unique is Overrated

Many men who want to change their style are obsessed with dressing differently than everyone else. They don’t want to wear the same kinds of clothes as other people. They want to have a unique style that stands out — but most of the time this makes them stick out like a sore thumb instead.

I always recommend starting with basic, timeless clothes, like solid white tees or navy blazers. But a lot of guys react by letting me know these clothes are too common for them. They’d rather get something that’s different.

But guess what?

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