“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.
Heads up! I put together a special beginner’s bonus for this post to 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 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.
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.
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.
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.
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
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.
9. TO QUICKLY UNDERSTAND QUALITY, GET HANDS ON
Why are some cashmere sweaters $100, and other $1,500? Is the $1,500 one really 15x better?
Are higher quality clothes “worth it”?
No doubt these questions have crossed your mind. And my answer is…
It’s hard to make anything good for a low price. Whether that’s a pair of jeans, a laptop, or a steak dinner at home. When you have a limited budget to work with, there has to be some compromises.
There’s an assumption that because higher quality or designer clothes are expensive, “you’re getting ripped off” as a customer. You’ll sometimes read guys on blogs and forums proclaim you’re just “paying for the marketing costs”
I can tell you having worked 11 years as a menswear designer, it’s just not really true.
Better materials, better construction, and better design cost more to make, so it costs more for you to buy.
A perfect example: Cheap jacket zippers can be low as $0.50 a zipper. They’re light, can be frustrating to use and, of course, break easily.
When I was making leather jackets, I was using high end RiRi zippers. They’re heftier and nearly impossible to break. When you zip up your jacket, it was buttery smooth.
The downside? They can sometimes cost as much as $20 per zipper for me as a designer. That means by the time the jacket hits you in the stores, that single $20 zipper adds $60 to the price of the jacket thanks to a standard 3x markup.
That’s not marketing, that’s math.
But it’s hard for you to grasp how much better that zipper or $1,500 cashmere sweater is without trying it. The same way I can tell you one of the best meals I’ve ever had cost $220, per person, no matter how well I describe it, you can’t truly understand until you take a bite.
WHAT YOU CAN DO TODAY: Go to a store that you would consider out of your budget. A place that might even be uncomfortably expensive for you. You don’t have to buy anything. Just walk around, touch the clothes. Maybe even try something on. Make mental note of how things fit, feel, and how you feel wearing it. Then go to a fast fashion shop like Zara or H&M and try similar items on. Make note of what’s different and what’s similar. Anything surprising?
10. BUY THE BEST QUALITY YOU CAN FOR YOUR BUDGET
This leads us to the question, how much should you spend on clothes?
Simple: My recommendation to all my clients is to buy the best quality that fits in their budget.
If you’re making mid 6-figures a year, then a $200 pair of jeans might not be a big deal. But if $200 is barely what you make a day, there are plenty of great options at lower prices.
WHAT YOU CAN DO TODAY: To start, I always recommend J.Crew. They’re in almost every major city, are classic with a touch of trend, and they have solid prices. For more store recommendations, check out my post “Where I personally shop (and what I get there)”
11. SAVE TIME IN THE DRESSING ROOM USING THE “PULL 3” TRICK
Whenever I’m out shopping, I always see people pulling one size, then going back and forth from the showroom to the dressing room.
It drives me crazy! It’s such a waste of time.
Imagine cooking a meal at home where you took out one ingredient at a time from the fridge.
I’m going to show you how to cut your shopping time in half with one trick.
When you’re pulling clothes to try on in the dressing room, “Pull 3” of the same item:
- One in the size you think you are
- One size up
- One size down
So if you’re shopping for jeans and you think you’re a 33, pull a 32 and a 34 and take all three to the dressing room. It saves you a couple trips, and is a bit of insurance in case it’s a new cut or the brand changed their sizing.
WHAT YOU CAN DO TODAY: Use the “Pull 3” trick when you’re out shopping
12. USE “THE SWAP TRICK” TO GRADUALLY STEP OUT OF YOUR COMFORT ZONE
There’s no change without stepping outside of your comfort zone.
But it doesn’t have to be terrifying.
I teach my clients what I call “The Swap Trick”. It’s a way of introducing something into your wardrobe – a new trendy piece, a new color they thought they could never wear, or an item of clothing they never considered before – gradually.
Here’s how it works.
Think of it like trying out hot sauces. You wouldn’t go from a mild hotsauce straight to a super hot ghost pepper sauce. You would try something slightly hotter than the last and work your way up.
It’s the same thing when you’re trying something new with your style. You probably don’t want to jump from a black leather jacket to a neon green one. The next step up would probably be a brown leather jacket.
Here’s another example:
You want to start wearing more colors and patterns for summer.
I’ll start with an easy outfit: linen oxford shirt, navy lounge pants, sunglasses, white sneakers. The color palette,while perfectly fine, feels a little boring and safe. So let’s swap out the shirt for something a little more colorful. We can go two ways, a brighter color, or a pattern/print.
Even though the choice of a light blue shirt isn’t so crazy, you can already see it feels a lot more colorful than the outfit we started with. With the print, it’s even better and more in the spirit of summer.
But notice how one simple swap can change the entire mood of the outfit! This is really the key to starting to wear more color. You don’t have to wear a lot to brighten up your look.
As a starting recommendation, I always advise to start with just one swap per phase. When you get more comfortable with wearing some color and patterns, take it a step further.
Each time, swap out one more item in your look for something a bit brighter and colorful. The great thing is, if you feel like you went overboard, you can always pull it back a level or two and still have a great outfit.
WHAT YOU CAN DO TODAY: Think about something you wanted to add to your style that you’re nervous about. How could you break it down and gradually introduce it into your wardrobe using “The Swap Trick”? If you need a specific example on how to use The Swap Trick for something like trends, check out this post I wrote on Effortless Gent.
13. YOU DON’T START WITH CONFIDENCE, YOU BUILD IT
Think about when you first started learning how to drive a car.
You were probably terrified.
You were pretty sure within the first 10 seconds of hitting the road, you were going to crash.
You weren’t confident. Yet, as you kept driving, your confidence grew. Driving got easier. Now you illegally Snapchat on your phone while sipping your coffee and playing with the radio as you steer with your knee, and still get work in one piece.
It’s the same with your style.
You don’t need to start with confidence to improve your style. Your confidence grows as you work to improve your style.
Just like with driving, the more you do it, the easier it gets.
WHAT YOU CAN DO TODAY: Start with one outfit. Just one. Use the advice in the previous tips – stick with neutral colored, classic styles that fit well. You’re going to look and feel great. That quick win is important. Now use that feeling to keep going. Then, read the next tip to learn my favorite trick to help you build confidence even faster.
14. USE MY FAVORITE TECHNIQUE TO FEEL MORE CONFIDENT IN A NEW OUTFIT
This is a great technique to use in conjunction with The Swap Trick, and is a KILLER hack for a first date. In fact, it’s something I used when I first started dating my current girlfriend.
Whenever you have a date (or a conference, interview, or speaking event): Wear the outfit you’re going to wear to date for an entire day before the date.
Even if it’s a dressy outfit. Go about your day like it’s any other day. Get coffee. Go grocery shopping. Go to work.
What you’re essentially doing is “breaking in” the outfit. Getting yourself used to wearing it.
I started doing this because I noticed that when I would dress up for a date, even if it’s clothes I’ve had for years, I would always feel uncomfortable during the date. I’d feel self-conscious. I’d fidget a lot.
Then one day I had schedule a date right after work, since I had no time to go home and change, I wore my date outfit to work. By the time the date rolled around, I had spent an entire day in my date outfit and felt relaxed.
WHAT YOU CAN DO TODAY: Whether it’s a new jacket you got or an entire outfit for a date, break it in by wearing it around to do errands. Got a last minute date or event and can’t spare an entire day? I’ve found even wearing the outfit for a few hours before helps.
Need some date outfit ideas? Check out this post: “A beautiful woman lets you know how to dress (and what to do) on a first date”
15. SEEK THE HELP AND ADVICE OF EXPERTS
According to Mint, I spent $7,360 last year on books, courses, and consultants to help me improve my business, my skills like writing, and general knowledge in topics I’m interested in like philosophy.
It sounds like a lot, but ask yourself this question: What’s the cost of bad advice?
Imagine you’re a CEO of a company and you have a marketing budget of $25k. You read some advice from marketing forums filled with anonymous writers. You decide to take some of the advice and it turns out to be bad. Now you’re out $25k. Suddenly, a $7k investment in an top expert seems like a steal.
How many months, even years, will you waste following bad advice when it comes to your fitness routine? Your finances? Your style?
This tweet from Amy Hoy sums it up perfectly:
When it comes to learning how to dress, there are TONS of options. From style blogs, Instagrams, Reddit, and Youtube channels.
Some dish out great advice. Most are filled with guys who like to shop and like to talk about it online.
When it comes to style advice, it can be tricky to filter out the good from the bad.
As someone that’s been doing this for over 11 years, I know how style advice can be challenging to teach. Telling someone what to buy isn’t the same as teaching them how to have great style. The same way a cook telling you to buy ingredients doesn’t help you learn the technique.
WHAT YOU CAN DO TODAY: Whenever you read advice online, always consider the source. Do they dress well? More important, is it a style you want to adopt? If they are a stylist or have products, how do their clients and readers look? Good, or terrible? Do they have a background in fashion or style, or are they “a regular guy just like you!”
Once you find an expert you’ve vetted. You have two options:
- Pay for their advice
This is the fastest way to learn. Whether that’s a book they’ve written, a course they’ve created, or hiring them for one-on-one time. And while this is the fastest, this is also the more costly option. This is my personal preferred way to learn because my time is limited. I can always make money back, but one thing I can’t make back is my time.
- Reach out to them via e-mail for advice
On the flip side, this option is “free”, but is going to take more time on your end. Before you reach out to an expert for advice, make sure you do your homework. Experts are often busy people. Make sure you search if they answered the questions you want to ask before. Skim through their blogs, Twitter, check if they’ve been interviewed on a podcast or magazine. If you can’t find the answer you’re looking for, only then should you consider reaching out to them. For that, I highly recommend reading this post: “How to get the attention of your favorite expert”
16. LEARN TO TAKE IT SERIOUSLY ENOUGH NOT TO TAKE IT TOO SERIOUSLY (AKA HAVE FUN, IT’S JUST CLOTHES)
I have a confession to make: I don’t read fashion blogs.
Sure, I skim sites like Hypebeast and Gear Patrol to see what’s new, but when it comes to blogs, forums, news about the industry, I stay clear. Why?
Well, for one thing, a lot of it’s really boring. It also doesn’t help me with my job.
I do a lot of research when it comes to learning the pains men have when it comes to their style. I often come across forums where guys are endlessly debating selvedge denim vs non-selvedge, having long discussions about the “death of original style”, and share their theories on what “DESIGNER X” was trying to say with his latest collection.
One thing I realized after I went from designing menswear to becoming a private personal stylist: I’ve learned to take it seriously enough not to take it too seriously.
Yes, great style can truly impact your life. I’ve seen it first hand.
Better style can make you get taken more seriously in your job. It can make you an unforgettable brand. And yes! It will make you more attractive! (What woman doesn’t want a well dressed, successful man?)
But the last thing I want you to do is spend hours on forums debating about clothes. I’d rather you put on an amazing new outfit (you learned thanks to me, of course), go out and live your life. Crush it at your job. Go on an amazing date.
Because if you aren’t having fun dressing better, it’s not going to last very long.
HAVING AMAZING STYLE IS EASIER THAN YOU THINK
To sum it up, make sure you:
- Buy clothes that fit – It will solve 90% of your style problems
- Focus on the classics first – classics are classics for a reason. They’re time tested essentials that look good on every guy.
- Stick to a neutral color palette – Neutrals automatically mix with each other, so you don’t have to worry about mixing colors. They make you look professional and masculine, and when you’re ready to introduce more color into your wardrobe, they serve as the perfect backdrop
- Have fun
Want to kickstart your new style in the next 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.