I’m just not naturally stylish. Does that sound familiar? Here’s the truth. Dressing well is a skill. And like any other skill, you can learn it and improve. Don’t believe me?
Yes, that’s me in high school rocking a terrible ponytail, along with glasses that were way too small for my head.
And to flesh out the image, my daily outfit in high school consisted of:
Plaid button up shirts
Baggy jeans with ripped hems because they were too long and I kept stepping on them
Clunky Rockabilly shoes I found at the mall
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.
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 STYLE 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. SOLVE 90% OF YOUR STYLE PROBLEMS BY GETTING THE RIGHT FIT
“F*@K Ryan Gosling!”
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.
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.
She was enabling his bad style.
After a couple of weeks, I promptly refunded his money and created this rule.
Change is uncomfortable for people. It makes them face the reality that someone is working hard to improve, and it challenges what they’re doing for themselves.
One of my favorite quotes of all time is “You are the average of 5 people around you.” Who we surround ourselves with has an extremely important impact on our actions, behaviors, and mindsets.
This is why wealthy successful businessmen tend to be friends with each other. It’s why fit attractive Crossfitters are surrounded by fit attractive Crossfitters in Instagram pics. And it’s why obese parents are more likely to have obese kids.
When it comes to your style, that’s exactly what you need if you want to improve. You need to surround yourself with people with the same goals as you.
WHAT YOU CAN DO TODAY:
The simplest change you can make is to start following stylish people on places like Instagram. It’ll give you a double whammy: It’ll expose you to great style and give you some inspiration, but it’ll also create an environment where dressing well is “normal”. Need some stylish Instagram recommendations? Check out this post I wrote about my favorite stylish Instagrams here.
5. FOCUS ON A CLASSIC STYLE FIRST BEFORE TRYING TO DEVELOP A PERSONAL STYLE
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.
6. THIS ALSO MEANS BUY CLASSIC STYLES FIRST BEFORE DABBLING INTO TRENDS
Tell me if this sounds familiar:
You open your closet. It’s filled with clothes.
You sift through all the hangers squeezed into your cramped closet and think to yourself “I have nothing to wear.”
So you go to the mall and buy even more clothes.
Then a month later, the same thing happens. You have “nothing” to wear.
You’re not going crazy.
This is what I call “Panic mode shopping”. You open your closet and freak out because things are outdated, they’re hard to mix, and there are so many choices. So you go out and buy more clothes and add to the problem.
It’s a vicious cycle. And one of the biggest reasons for this problem is trendy clothes.
Trendy translates to what’s cool now. It’s what all the blogs and magazines are talking about. It’s what’s in the stores. And because it’s new and fresh, it’s a little exciting.
But the big problem with any trend is that it eventually dies down.
Remember how leather sweatpants were really popular a couple years ago? And what about double monk shoes before that? Or if you’re old like me, trucker hats?
Trendy clothes are like that big Summer blockbuster that you can’t escape.
The actors are on every talk show. Commercials are playing non-stop. Posters are everywhere. But, come Fall, we’ve moved on.
Classics styles are like classic movies. The Godfather. Back to the Future. Taxi Driver. They’re not going anywhere.
That’s the advantage of classic styles of clothes. They’re time tested to look good. A leather jacket, dark blue jeans, boots? Looked great in the 1950s, still looks good today.
WHAT YOU CAN DO TODAY:
Start shifting your shopping habits to look for and buy classic styles. What’s the difference between something that’s classic and trendy? How do you balance classics and trends in your wardrobe? Check out this post I wrote that answers that question.
7. STAY CLEAR OF GRAPHICS, LOGOS, AND WILD PRINTS (FOR NOW)
Many Essential Man readers are older professionals (30+), and I often get asked “How can I look older/more mature/get taken more seriously?”
One of the ways is to stay clear of graphics, logos, and wild prints on any kind of clothing, whether it’s a t-shirt, sweater, or god forbid, pants.
Whenever you wear a logo or graphic t-shirt, you either look like you’re in college, or are you’re on your way to a UFC fight. (Don’t get me wrong, I’m a HUGE MMA fan. But there is a certain style that goes with it.)
I’m not opposed to logos and graphic t-shirts as part of a solid wardrobe, but when you’re starting out, going solid colors is going to make you look 10x more mature and serious.
WHAT YOU CAN DO TODAY:
Solid colors and graphic/logo-less clothes make you look more refined and mature. The great thing is that this change is a simple swap. Replace your graphic t-shirts and clothes with solid versions, like with the examples above.
8. STICK TO SOLID NEUTRAL COLORS
Every man’s wardrobe should be based around neutral colors.
What are neutral colors?
They’re colors that aren’t overpowering. Because they’re not overpowering they easily mix with each other. Powerful colors like a neon green and orange? Pretty hard to work with.
If your wardrobe is all neutral colors, you don’t need to know “how to mix and match colors”. A neutral color wardrobe is essentially self-working!
Here’s the other thing: You’ve probably already been dressing in mostly neutral colors without even knowing it.
Neutral colors are white, black, navy, olive, grey, khaki, brown
Standard neutral color palette
What I love about neutral colors, aside from it being self working, is that it’s a very masculine color palette. It makes you look refined, serious, and put together. It also provides the perfect backdrop when you want to start introducing more color to your wardrobe.
WHAT YOU CAN DO TODAY:
I recommend a ratio of 3:1 when it comes to solid neutrals and non-neutral colors. Take 10 minutes check your closet. Do you have more non-neutrals, graphics and pattern clothes than solid neutrals? Make a note to start balancing it out to hit a 3:1 ratio.
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