Beginner’s Guide: Essential Style Tips For Guys Who Want to Dress

It wasn’t until college did I start paying attention to my style in a serious way. And if that kid above could learn, so can you.

In fact, you have a huge advantage as an Essential Man reader. I didn’t have a real resource, and had to go through years of trial and error before I’ve truly learned what great style was.

Today I’m sharing with you essential style tips for guys who want to dress better.

Whether you’re a complete beginner, or have been working on your style for a while and need a refresher, I’ve refined these concepts and tips over the last 11 years to help you look your best in no time.

Heads up! I put together a special beginner’s bonus for this postto help you kickstart your new style in less than 10 mins!

Download my “How Clothes Should Fit You” Cheatsheets. You’ll learn “clothing fit” hacks that’ll help you find clothes that fit, cut your shopping time in half, and make you look really fucking good – even if you have a “weird” body type.

You can learn these simple tricks in 10 minutes. And best of all, it’s free! Just enter your info below and I’ll send it to you!

1. Realize that dressing well is a skill

Just like cooking or shooting free throws, dressing well is a skill that can actually be learned.

My job as a personal stylist isn’t to buy clothes for guys and send them on their way. I teach men how to choose clothes that enhance them so they can do it on their own. If dressing well wasn’t a skill that could be taught, I’d be out of a job!

With all skills, you get better the more you practice. And unless you live in some weirdo nudist colony (I would apologize here, but if you’re a nudist reading this blog, you’re in the wrong place), you need to get dressed everyday. That means you have an opportunity to practice and nurture the skill of dressing well every single day.

WHAT YOU CAN DO TODAY: Nobody is born in a perfectly tailored 3-piece suit, or with some magical intuition on how to dress well. (If you need a reminder, scroll back up and look at my high school picture again.) Realize that dressing well is a skill that can be developed through practice.

2. Develop your “eye” by identifying styles you like

Right after guys tell me that they’re just not “naturally stylish”, it’s often followed up with:

“I just don’t have an eye for putting together outfits or knowing what looks good”

Here’s what I tell them:

“Ok. Is there anyone who’s style you think looks good? Something you think ‘I’d like to dress like that’, even if you don’t think you could pull it off. Maybe it’s a celebrity, a musician, an athlete? Even a fictional character. Some of my clients have mentioned James Bond or Tony Stark before.”

The guy will then list off a ton of men he thinks dresses cool. And then I like to point out that he just debunked his own assumption that he doesn’t have an “eye”. He just showed me he can see and recognize great style!

Now, he might not know the why yet, and that’s often the reason why guys tell me they don’t have an eye. Understanding why is learnable.

But whenever you’re working on a goal, it’s important to identify and challenge stories you tell yourself. Whether it’s that you don’t have an eye for style, you’re too busy to work out, or you’re just a shy person. The stories we tell ourselves are often invisible barriers to keep us in our comfort zone. 

WHAT YOU CAN DO TODAY: Take 5 minutes. List out 3 or more guys who style you think looks great and that is in the direction you’d like to go. Even if you don’t think you can pull it off, list it. It could be someone you know, a celebrity, or even a fictional character from a movie.

3. You can solve 90% of your style problems by dialing in your fit

This is something an actual client said to me once after seeing the picture of Ryan Gosling above.

“How the hell does he look so cool wearing just a t-shirt and jeans?”

The answer, my friend, is fit.

Fit is the most important thing when it comes to great style. It’s so important, in fact, that I tell every one of my clients “wearing clothes that fit properly will solve 90% of your style problems.”

When clothes don’t fit properly, they throw off your body proportions. Because of the excess fabric, clothes that are too big make you not only look sloppy, but fatter and shorter than you are.

Men have the tendency to wear clothes that are too big for them because it either “feels more comfortable”, or they just don’t know how clothes are supposed to fit in the first place.

The right fit is how someone like Ryan Gosling (or me, or you) can look effortlessly stylish rocking a plain white t-shirt and jeans, and how someone can look terrible in a “nice suit” that probably cost 20x more.

This also means if you think you need a suit in order to look stylish, you don’t!

If you’re more leather jacket and jeans like me, you can be leather jacket and jeans and look great, as long as you’re wearing clothes that fit right.

WHAT YOU CAN DO TODAY: “How Clothes Should Fit You” Cheatsheets which shows you my trick to mastering the perfect fit for your shirts and pants in 10 minutes.

4. Surround yourself with stylish people (even if it’s online)

When making any change in your life, especially something that’s physical like your style, the biggest roadblock is going to be the most surprising.

When it comes to the people around you now, your friends and family, your girlfriend, your coworkers, there is a high likelihood that they won’t all have a positive reaction to your change.

If you want to work with me one on one as a client, you have to agree to work with me solo. That means your girlfriend or wife is not allowed to sit in to any of our sessions or shopping trips.

I created this rule after working with a client whose wife insisted she sit in in our styling sessions. She would give me feedback on every single piece of advice I’d give. Her notes and comments amounted to “He doesn’t like that, he prefers to wear this.” Essentially negating any advice I would give.

5. Don’t worry about building a unique personal style (yet)

A mistake people make when trying to improve their style is thinking they need to create an original, 100% unique personal style.

This is a classic example of what’s called “Extreme thinking”.

Want to lose 20lbs?

“Ugh. I have to give up bread, rice, beer, alcohol, candy, meat AND have to do some crazy crossfit workout, and spend 2 hours at the gym. Forget it”

Want to save money for a vacation?

“That means I have to cancel my Netflix account, stop going out on weekends, defer my student loans. I probably had to miss some credit card payments if I ever want to have fun. That’s going to ruin my credit. I’m never gonna be able to relax on vacation now.”

When you’re starting to improve your style, think of it like how chefs learn to cook:

They don’t go into the kitchen thinking they need to create some amazing and original dish never seen before.

They learn the classic recipes and techniques first.Then they start adding bits and pieces of their personality and interests in to put a spin on them.

You’re going to do the exact same thing with your style.

Focus on classic styles first, then slowly add your own personal spin later.

WHAT YOU CAN DO TODAY: I write about classic styles in my “Essentials” series, you can see all the Essentials I’ve written about so far by clicking here.

Leave a Comment

Your email address will not be published. Required fields are marked *