in: Featured, Outfit Guide, Style

• Last updated: September 25, 2021

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

Two college students sitting on bench and looking to camera.

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?

Personal style doesn’t come from being different. It comes from knowing what makes you look good and what doesn’t.

When you start with basic items, you’ll learn that an understated outfit makes you look more put-together and mature. Then, after some time, you’ll learn to get more creative.

That’s when your personal tastes start to develop. That’s when you start adding a personal touch. And that’s when you develop a style that feels more like you than you’ve ever felt before.

That doesn’t mean it will be 100% unique. (Hardly anybody’s style is.) But it will be 100% you.

5. The Wrong Clothes Will Exaggerate the Physical Issues You May Be Trying to Play Down

Clothes can affect how people perceive your physical form, both negatively and positively.

A billowing shirt will make a large man look larger, and a skinny man look skinnier. Horizontal details can make a short man look shorter, while a lack of them can make a tall man look lanky or looming.

On the other hand, a well-fitting jacket and a pair of high-rise pants can make a large man look slimmer. A checked shirt or textured sweater can make a skinny man look bulkier. Vertical stripes and textures can make a short man look taller, while horizontal stripes can break up a tall man’s height.

You should find out which types of clothes flatter you most and which exaggerate your body’s least attractive qualities. Play to your strengths and chances are people will wonder whether you’ve been hitting the gym.

6. Style is NOT All in the Details

People often say that style is all in the details, but I disagree. Style is all in the overall look.

Don’t get me wrong; details are important. But many men take this advice and think all they need to do is mind the details of their outfits. They think all they need to do to look sharper is make a few, tiny changes. But that’s not how it works.

Most men have much bigger problems than a few details that are off.

So before you worry about the details, you should focus on ensuring that your outfit works as a whole — that the larger parts of it are balanced and work together to look appealing.

You should focus on ensuring that the fit and the cut are right for you, that the colors look good on you, and that the individual clothes look good together. You can worry about sock color or pocket squares after you’ve mastered all those areas.

7. Fewer Clothes Can Offer More Variety Than a Bulging Wardrobe

You want to avoid looking the same day in and day out, right? You want to keep your look fresh. But that doesn’t mean you need a wardrobe that’s bulging with clothes.

I used to own tons of clothes, but the more I got the hang of dressing well, the more I realized I didn’t need that many. I could create plenty of outfits with just a few of them, and you can too.

First, you need to stop seeing clothes as parts of an outfit and see them as parts of your wardrobe. Every new piece you add should click with several (if not, most) clothes you already own. So if you have a lot of blue or green in your wardrobe, choose colors that you like wearing with blue or green.

Also, you want to have a base of simple clothes in neutral colors and without any patterns because they’ll go with almost everything you’ll add to your wardrobe.

In most men’s wardrobes, 20 pieces of clothing might create 10 good outfits.

When you choose wisely, 10 clothes can create over 60.

8. You Can Rebuild Your Wardrobe on a Shoestring Budget

When you start upgrading your look, you’ll discover at some point that most of your current wardrobe no longer cuts it for you. Most of your wardrobe will have to be replaced. And you may think this will cost a fortune, but you probably overestimate the cost (just like I once did).

Maybe you only go clothes shopping once in a blue moon and splurge when you do. This habit has caused you to associate clothes shopping with high expenses. Maybe you weigh the cost of a whole new wardrobe against your monthly wage and think there’s just no way. Or maybe you just think you’ll need to invest in more expensive, top-quality clothes.

But you’d be wrong on all accounts.

First, if you go shopping once a month and only buy a few items at a time, it turns out to be quite affordable.

Second, you’ll take a while to build your new wardrobe. If you want to compare the cost to anything, compare it to your yearly wage, not your monthly wage.

Third, you can look great in affordable clothes too. In fact, you should experiment with more affordable clothes before you invest in top quality.

Simply set a monthly budget and rebuild your wardrobe on a pace you can afford, and you’ll see it’s more affordable than you thought.

9. “Dress to Express” Trumps “Dress to Impress”

One of the most-common style tips you’ll ever hear is, “Dress to impress.”

It’s also one of the emptiest tips you’ll ever hear because how do you impress people you’ve never met? Do you peek inside their minds?

You can only guess what will impress someone, so dress to express instead.

Your clothes are a form of expression. They’re supposed to express something about who you are. So use them to express positive qualities.

When you have a business meeting, you may wear something that expresses your professionalism. When you have a first date, you may wear something that expresses your easygoing nature. Whoever you’re meeting with, ask yourself, “What qualities of mine do I want to express to this person?” and then dress accordingly.

Use your clothes to express the best version of you that you can be — in any given situation. Make an effort to look your best, but don’t show up as someone you’re not.

You don’t have to put up a facade to make a great impression. You just have to be the best you that you can be. So dress to express that version of yourself.

Dressing Well is Easier Than You Think

You don’t need to change your style in huge ways to improve it. You just need to change the right things.

Stop focusing on trivial details. Stop trying to fix your style with a suit and tie. Stop thinking you need to change your whole look in a day.

Focus on figuring out what truly works. Focus on the basics. And before you know it, you’ll be putting awesome outfits together with barely any thought.

You’ll be the one that seems to have a natural sense of style.

You’ll be the one other men look at and think, “How does he do it?”

You’ll be the one that makes it look so easy.


Robert van Tongeren helps men become better dressers at Restart Your Style. He’s on a mission to simplify the art of dressing well and make it easy for you to get started. If you’re looking for simple ways to boost your style sense, check out his e-book The Beginner’s Guide to Dressing Better.

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