Fashion is for everyone, but a successful sense of style is not! So many guys today dream of dressing like James Bond, Harvey Specter, Don Draper, etc. yet, so few actually do so. Why is that?
Well, it means dressing with class, and that’s something most guys don’t want deal with.
It also means being a high performance person. How you dress is how you feel. Unfortunately, most guys would rather take the lazy road. It’s far easier and you know what, it’s pathetic!
A man strives for greatness; to be at his personal best. You are given two choices every single morning after waking up, and I’m not just talking about going back to sleep or starting the day.
I’m talking about dressing for success, or dressing like a bum! When you become a man, mom and dad aren’t there to dress you every morning like they did when you were a kid. The choice of what to wear is entirely your own.
Why settle for less in life, when you can show the world the most successful version of yourself?
You won’t just look better. You’ll feel better about yourself, work harder towards your goals, get more respect (from both women and your peers), and so on.
If you want to dress like a loser, no one will stop you. If you want to know how to dress like a successful man, I’m here to help.
Dressing like a man it doesn’t mean you must spend big boy money, though it certainly helps.
You don’t need a hundred eBooks or fashion coaches either. In a moment here you’ll know why this is true.
The only thing required is to understand two of the most important rules:
1. It takes time to discover your own, unique sense of style!
Spend all the money you want. Hire all the fashion coaches in the world. And guess what the result will be? An excellent set of threads covering up a man who’s uncomfortable in what he’s wearing.
You can rush the process all you want. However, confidence in your clothing comes from one person only: You!
Think back when you were a kid.. Remember all those times your parents made you wear a suit for special occasions? You probably looked great! However, for most young men, it still felt uncomfortable and a bit awkward. Then something happened. When you started to become an adult, you started wearing things like suits, dress shirts, etc more often. Suddenly, those uncomfortable clothes started to seem more natural and enjoyable to wear.
Why am I telling you this? Well, most guys today try to go from t-shirts and shorts to suits and the end result is an outfit they don’t feel confident in. They assume they look handsome, but the reality is it doesn’t truly fit them personally. It’s not their style, it’s out of their element, and in other words, it’s going to take some time to get accustomed to. And guess what, people notice!
Now, I know what you’re thinking. Actors and stars have all these fashion coaches at their side.. I’d look just as good too! That’s just not true. They’ve been in the spotlight their entire life. They know how to put on a good impression, regardless of their mood or comfort level. That’s something most men can’t do! In reality, it takes them years to master that type of talent. Go volunteer as an anchor on a TV show for a day, and tell me how miserable you look on the screen!
The truth is, if you want to look and feel you best you have to believe it! That means being able to pick out your own set of threads confidently. You can put all your trust in someone else and keep questioning it, or start trusting yourself to make the right choices. Remember, being a man involves making your own decisions in life.
My point is, either route requires time. I’ve met plenty of men who started off reworking their fashion in their 20’s after college, and didn’t truly feel dapper until their early 30’s. Most guys end up getting caught in trends (or worse just give up), only to realize and finally say, “what the fu-ck am I doing” later on in life.
Remember, finding your own unique sense of style takes patience. Don’t rush the process without thinking first. In a year’s time or sooner, you will on regret those mistakes; regardless of the sale price or past trend. Invest time into discovering what you personally like. You’ll have to pick out your attire every single day, for the rest of your life. These are decisions that only you can make! Slowly, but surely you’ll master the art of dressing with class and charming style. Be okay with experimenting and failing, because I will tell you now, just like anything in life, fashion requires a lot of it!
2. Dress to be a high performance person!
When you want to look your best what do you wear? A Suit.
Every man knows that.
So, why do guys save their suits for weddings and funerals only? It’s as if every other day doesn’t matter at all.
Let’s face the reality here, you don’t need a “special occasion” to dress well and to dress with class! All you need is a desire to be successful. Unfortunately, most guys don’t have it in them! Instead, they give themselves all these excuses, “suits, ties, etc are so uncomfortable”, “I’ll look weird”, “I’m not a CEO”, “I can’t because…” ALL of it is nonsense!
Either you’re aiming for success every single day or you’re accepting failure. It’s YOUR choice. You set the tone every morning by choosing what to wear. And if you think you won’t be far more successful wearing a classy set of threads, you’re NOT being honest with yourself.
Wear a suit and tie for the next 30 days, I challenge you. If you think that’s easy, it’s not. Most of guys won’t even last a week! Wear one to the grocery store, work, dinner out, etc. You’ll be amazed at how dramatically your view of fashion changes, how people treat you, and how you treat yourself!
Understand that I’m not trying to say you MUST wear a suit every single day of the year here. However, when you start wearing them often enough, things like your business casual and even casual attire will also improve. You’ll find yourself being more comfortable with ties, dress shirts, blazers, etc. Eventually you’ll change the way you view yourself, and others will notice.
If you want to dress like a bum and be treated like one, that’s up to you. Laziness has always been the opium of the poor man!
If guys would start dressing like the most successful versions of themselves, almost all of their fashion problems would vanish.
With that said, now you know the two most important pieces of advice for how to dress like a man. If you follow them, and take note of these small bits of wisdom below, you’ll be headed in the right direction.
Ditch the t-shirts, go with dress shirts.
T-shirts are the lazy man’s way of approaching fashion. In reality, they are the absolute bare minimum. Most places require them alongside shoes to enter the door; I think that should say it all.
One of the biggest excuses I hear all the time is: “T-shirts are the most comfortable thing to wear.” The truth is, you’d be a lot more comfortable in a suit or dress shirt if you took the time to wear them more often!
Now, t-shirts have their place in the world of apparel, for instance, when you’re building a deck outdoors in the summer. However, you can’t sit there and tell me you need all the comfort you can get when you’re going out to eat lunch with a friend.
When it comes to cost, don’t fool yourself. Just because you were willing to shell out hundreds of dollars for a designer label doesn’t change the fact that it’s still a t-shirt! Remember, the man in the dress shirt will always be met with more respect than the other in a t-shirt.
Jeans, the Swiss Army Knife of the fashion world.
Sure, jeans aren’t in the realm of formal wear, however, they still offer a lot of universal appeal. With the right pair, you can easily go from casual to classy by throwing a blazer and pair of dress shoes in the mix.
Where most guys go wrong with jeans, is when they try to avoid the dreaded “dad look”. Now, there’s nothing wrong with that however, the moment you start adding things like: Tacky rivets, ultra-thick and ultra-high contrasting stitching, trendy wash and distressed styles, overly baggy cuts, etc. you start running into bigger problems.
Avoid all of that! The truth is, a pair of well-fitting dark blue jeans is on par with the timelessness of a fine suit. They never go out of style.
The next time you go out shopping for a pair, start thinking about jeans like you do dress pants. Buy a pair that fits you really well; by that I mean not skinny nor baggy. More than often, slim will be your best choice. Pass all the trendy and popular styles over, and opt for a simple, clean dark blue dye.
If you take note of how people perceive dad jeans, you’ll notice two things: First, they aren’t baggy however, they are always far too roomy and it’s quite obvious. Second, the finish is always light blue. The jeans might be brand new, but the blue dye looks like it was washed away years ago.
In regard to materials, like raw denim, don’t worry about it too much. Buy what you want. Remember, all jeans fade over their lifetime. Eventually, you’ll need a new pair to keep your style sharp.
Wear a tie properly.
Any man can wear a tie. Some struggle with tying them together. But by far, the biggest challenge of them all for the majority of men, is knowing how to actually pick the right one out.
Instead of choosing a tie that’s more reserved and subtle, so many men go all in with flashy patterns and rather bizarre colors. Most without even realizing it! Their tie becomes the centerpiece of attraction for all wandering eyes and it screams, “Look at me; ignore everything else!”
Now, there’s nothing wrong with a little contrast; a good tie should have some room to speak up. However, it’s really easy to overdo it; I mean really easy. Learn where to draw the line, it takes some time.
Here’s what usually happens:
You go to an average local suit store, say Jos. A Bank or Men’s Warehouse. (Now, there’s nothing wrong with the two, in fact, I shop them myself from time to time.) You pick out a new suit, or perhaps just some dress shirts and pants. You realize you need a tie or a few.
The salesman comes back with a handful of inspiration. He convinces you that this goes with that and so on. You aren’t even sold hard; you just agree, because you have similar tastes. You pay for your clothes and go home.
Guess what? You took fashion advice from the bottom of the barrel! Sure, help in any form is always appreciated, but in order to dress like a man, you must understand how to coordinate your attire on your own. Remember, people have their own idea what looks good. They have their own sense of fashion, and nine out of ten times, it will never be the exact same as yours!
As much as I hate to say, a lot of the advice you get, is more than often, sh-t. Salesmen are excellent at showing you the ropes of fashion, but beyond the basics, your luck will run out. Understand, even small items like ties can make a big impact on your overall presentation. Unless you have Tom Ford at your disposal, or another person who lives and breathes fashion, it’s worth spending some time in learning how to properly match a tie to a dress shirt.
Just consider the business world. If someone’s giving you advice on success, and they’re not at a level you wish to obtain or have failed to reach it themselves, it means absolutely nothing! If your salesmen is selling you on fashion and their own attire is anything but, avoid their advice.
Accessories in moderation.
Your clothes often speak for themselves when it comes to your level of wealth, professionalism, etc. Your accessories often speak for your level of detail and patience.
The truth is, accessories when done right, appear natural. Anyone can throw on a diamond necklace and call it a day. However, few can blend a tie bar or pin, cufflinks, pocket square, watch, etc with subtle perfection.
Remember, accessories work by pulling your entire look together. Each piece draws in bits of attention with interest and charm, rather than with obnoxious banter.
Get acquainted with things like the pocket square and lapel flower. Most guys don’t wear them for one reason or another. Which, to be honest is quite a shame. In reality, most men who are successful with fashion gladly welcome those two pieces in their attire without any hesitation or second thoughts.
Drop the logos.
Unless you’re in a sponsorship, it’s time to leave behind anything that’s plastered in logos. Let your sense of fashion do the talking for you. NOT some brand’s marketing.
The same thing can be said about graphic tees. While some of them are rather funny or artistic, consider this: Would you wear one while you’re asking your boss for a raise? Obliviously, not. So, why limit the level of respect you receive from the world on a daily basis? If you want more success in life, dress for the part.
I remember when A&F was the cool thing to wear back when I was a kid. Today, no one gives a sh-t! Even A&F themselves have made moves to make their logos smaller and significantly less visible. Just think about all the high-end designer brands for a moment here. The majority of their clothing lines subtly hide their branding or keep it to a minimalist approach.
Understand that it makes no difference what the price tag is; a logo at the end of the day, is just that. It falls right into branding and marketing. Even Gucci could put out a tacky five-thousand dollar belt if they wished to do so. If it looked terrible, the signature G pattern isn’t going to change a damn thing! Never confuse the price of an item in relation to how well it looks. Sure, most high end brands offer really sharp pieces of clothing; it’s what they do. However, even the best make mistakes from time to time. Remember, buyers and designers are humans too.
Buy based upon what you like, not what it costs, or who it’s made by! Quality aside of course.
Personally, I’d rather own a pair of fine leather dress shoes that took a leather-worker hours to make by hand. You know, the ones that are hand dyed, cut and sewn to perfection. (As if the fresh smell of leather itself wasn’t intoxicating enough.) Over… Some sneakers that were injection molded with economical rubber overseas, and in a sweatshop that pumps out hundreds of thousands of pairs a day.
But that’s just me.
Now, when it comes to sneakers, you wouldn’t wear them with a suit. Every man knows that. Sure, some sneaker obsessed collectors might, but that’s their passion in life. In reality, sometimes passion over takes fashion.
Regardless, sneakers ruin more than just the charm of a fine suit. When you start wearing them every day, you start putting a major strain on your more casual attire too. Save them for places like the gym. Remember, if you’re don’t plan on running or shooting hoops, ask yourself, what reason do you have to wear them?
Don’t give me the comfort excuse! Dress shoes are no different than t-shirts and dress shirts.
However, you must still understand that shoes are supposed to be fun. Everyone likes to laugh at how women are so obsessed with their shoe game, but the truth is, men with great fashion senses know exactly why this is! You don’t have to wear bland brown or black leather dress shoes in order to look like a success. Get the idea of formal wear out of your head.
When it comes to shoes, go with an interesting pair. If you don’t think women will notice, trust me they will. More so than you ever will. Even shoes with colorful laces are fine. A red blazer with red laces on a brown, boot often adds a little bit of character to your attire. Remember, it’s all about the details!
In reality, it’s hard to go wrong with a fine pair of dress shoes or boots. The same can’t be said about sneakers. Very few go well a good outfit. Think of it like finely crafted timepieces. Once you get up to a certain level of craftsmanship, the variations in each watch simply add subtle uniqueness. For most sneakers, what you end up getting is over the top, attention-grabbing logo patterns, colors, etc.
Know thy tailor.
Clothes that fit right are more than half the battle.
In any given city, there are always a handful of tailors who can make clothes made for just about anyone, fit like they were made exclusively for you. Take advantage of that luxury. It doesn’t cost much, though, your tailor will ALWAYS be worth every single penny.
Most guys ignore this, even though it’s the heart of what makes a suit look terrible vs. exceptional. However, it goes beyond suits, your dress shirts and pants need love to.
Understand that S, M, L, etc. sizes are like the fast food of fashion. Their convenient, but they don’t do your style any good!
A change of underwear.
Boxers are like a lot baggy pants. While you should avoid trends, the reality is, there are certain styles of underwear worth moving on to.
Treat yourself and your woman, who will respect you even more after doing so, to a pair of boxer-briefs or at least a pair of briefs or trunks.
If you like patterns or more vibrant colors, you can take comfort in saving those for your underwear; rather than trying to display them for all the world to see on a graphic t-shirt or tie. Sure, solid colors are king in the world of underwear, but if you want to have a little fun with your style, underwear makes for a discreet way to do it, all without ruining your overall style.
Trade in the backpack.
If you’re not in college or going camping, trade in the backpack for a briefcase or messenger bag. Remember, if you’re going to be carrying it by your side, it’s going to ultimately affect your presentation. Who would you rather do a business deal with:
A man who digs around a backpack filled with gear and garbage… Or a man who slips out an important document from the side of his briefcase?
Remember, it’s a lot like shoes. Sneakers serve the same purpose as dress shoes. However, sneakers don’t measure up to a level of professionalism, nor gain respect the same way dress shoes do.
Learn to layer clothing.
Consider the suit, now the three-piece suit. It’s a subtle change, but noticeable. Layering works wonders, even outside the suit concept of course.
It’s a shame it gets so little attention in most style guides, when in reality, it’s a great way to go from acceptable to outstanding in appearance. Now, it does take a lot of practice to perfect it, and just like ties, it’s difficult for most guys to pair things together. However, that doesn’t mean you should rule it off your list.
Honestly, even I have a really hard time layering. Finding the right pieces to fit my style isn’t a simple process when stores don’t carry what you like. But I still do it and love it. Don’t get discouraged and give up on it early. You’ll eventually find all the pieces to the puzzle.
Match your belt to your shoes.
It’s a simple rule really, but like most simple things in life, it’s easy to forget. If you’re wearing brown shoes, wear a brown belt. If you’re wearing black shoes, wear a black belt.
When it comes to buying a belt, spend your money wisely. Avoid the cheap faux-leather; it will always deteriorate within a year’s time. Genuine leather is always worth the extra dough.
Lose the white socks.
Go black, brown, navy, or get creative and add some character to your look with color or patterns. Remember, socks like shoes should be fun. It’s worth noting that socks with sandals is never a good look!
Know your face shape.
When you do, you’ll be able to pick out the right pair of sunglasses without having to question if you look or not. You’ll also have a better idea of what haircut and beard styles to go with.
Wear blazers and suits.
Are everyday essentials, wear one or the other. I find it funny so many guys wished they looked like James Bond. Yet, none of them are willing to wear a suit or even blazer every day. Imagine that!
You can buy all the trendy clothes in the world, and yet, they will never compare to the timeless and dapper appeal of those two.
Understand one thing: A suit is never too fancy to wear every single day! Period. Only poor people with no class say sh-t like that. You can never be over-dressed for any occasion, but you can always screw up by being underdressed.
Suits, like blazers get you respect and the right kind of attention. From the banker to the gas station attendant, wear them and you’ll notice how people start treating you differently. In reality, their treating you like a man.
If you’re friends, family or co-workers want to complain about your style choices, ignore them. Their level of success won’t always match your own. Sure, they may often get upset to see you doing something they are too afraid or lazy to do themselves.
Save the gym clothes for the gym.
I already covered the t-shirt and sneakers bit earlier, however, the same is just as true for sweatpants, gym shorts, etc.
Go easy on the prints on colors.
If you want to get a little creative in the underwear, shoe and sock department, fine. However, when it comes to everything else, try to tone it down a little. Remember, good fashion is subtle in terms of attraction, it doesn’t not have to scream for attention.
Consider Matthew Lesko and his famous question mark suit. His style is over the top and hard to ignore, but for his business goals it works wonders. His mission essentially is to stop every single eye ball. Unless you’re in the same line of work, chances are things like a tropical, floral pattern suit or dress shirt aren’t going to work as well for you.
It’s really easy to go into that ugly Christmas sweater territory without realizing it. Pin-stripes, bold colors, patterns, etc in excessive amounts are the fastest way to fail in fashion. Remember, even solid colors, subtle prints, etc are perfect fine! If you aim to dress with class, your outfit no matter how bland, will always fare better than one that goes too far.
There’s more to fashion than just clothes.
The truth is, you’re grooming affects your presentation just as much as your apparel does.
Though, I’m not talking about just how you smell here. Every guy knows how to take a shower or bath, wear deodorant, etc. Sure, some men pour on the cologne too heavy, but that’s another story.
In reality, I’m talking about things like: Getting a real haircut. You’ll be amazed at difference between a $10 cut and a professional, $50-$100 cut. Sure, it’s expensive, but in the grand scheme of things, you could spend $50 on a dress shirt in comparison.
Not to mention, things like trimming your fingernails. Stop biting them, clean them out.
Spend some time learning the ropes of skincare. There is far more to it than just soap, face wash and shampoo!
The same can be said about hair care. What you see the little men’s grooming isle at the supermarket it is quite literally, pathetic. Your hair may hate gel or pomade, but be tamable with hair spray or wax. Perhaps you need a little powder to pump up the volume. I could go on here… Interestingly enough, some of the best men’s products aren’t even labeled for men. It takes some experimentation. As a man, you shouldn’t be afraid to do that.