There was a time in my life, some years ago, when I was too timid to ask a stranger for directions.
I was so uncomfortable in my own skin that it was paralyzing every aspect of my life.
During that time, I frequently found myself in thrift shops and bookstores where I would scan all of their self-improvement books, eagerly searching for some pearl of wisdom that could tell me how to fix myself.
Reinventing my style
Though I learned a lot from those resources, I still wasn’t who I wanted to be.
Most of these books focused on fixing yourself from the inside first – which is really great advice for most people.
But after some serious introspection, I pinned my displeasure with my physical appearance as the driving source of my shyness. So I began working to solve that problem, through training my body and then dressing it well.
Over the many years it’s taken me to get where I am, I’ve had the opportunity to experience first-hand how improving your style can enhance your life.
Why you should want to dress better
I talk a lot about how to dress better, but it’s equally, if not more, important to discuss why you should dress better.
There’s a reason that nearly all self-improvement books and websites have a fitness and style component.
How you look on the outside reflects how you feel on the inside. It’s like a window to the man underneath.
Perhaps a sloppy appearance is the result of a careless attitude. Or maybe it’s a lack of confidence stemming from being dissatisfied with one’s outward appearance, as was my situation.
Whatever the case, the outcome is the same.
People treat you according to how you present yourself. And style is a huge component of your presentation.
For example, I was pushing my daughter in her stroller around the neighborhood recently. We walked past a local bar where two guys were outside smoking. One of them had an exceptionally sloppy appearance.
He was about 30 years old, obviously out of shape, and wearing a backwards cap, Chicago Cubs t-shirt (that came down past his elbows), HUGE gym shorts, and rubber flip-flops.
Now, I’m truly not a judgmental person, but my mind made some automatic assumptions about this man. He appeared lazy, maybe he didn’t have any direction in his life, and why was he at a bar at 1pm on a Wednesday?
Then he threw his cigarette butt in the street, walked over to a pristine, white Audi S5 and fired it up. Then my mind started formulating a different story.
“He’s probably just taking a few well deserved vacation days to wind down from his high stress career.”
I really don’t concern myself with what other people look like and I don’t hold anyone else to my style or grooming standards, but my point is that these assumptions were automatic, basically involuntarily.
My Transformation: Inside and Out
When you make the conscious decision to reinvent your style and start presenting yourself in a different way to the world, a whole host of new people and opportunities are going to present themselves to you.
Here are the ways my life has changed and I have changed, inside and out, since reinventing my style.
(P.S. Don’t miss the style challenge I’ve laid out for you at the end!)
What changed from the inside
I’ve taken on the characteristics of how I dress
Simply dressing like a confident, successful person has shaped my frame of mind and, as a result, my actions.
I went to college after spending 4 years working as a mechanic and construction worker. I embraced the luxury of being able to shower, get dressed, and stay clean for the rest of the day.
My classmates considered getting dressed up to be a chore and preferred to stay in their pajamas while attending class.
I almost always put forth more effort and took school more seriously than they did. Sure, personality and experiences had a lot to do with it, but dressing the part sure didn’t hurt.
I was dressing to kick some ass and they were dressing to lounge on the couch.
Don’t let the way you dress pull your mindset and actions in the wrong direction.
By waking up, taking a shower, and putting on the appropriate clothes for the day ahead, your mind is somehow better prepared to handle anything that comes your way.
My mind has become free
Since I began feeling good about my appearance, I have the freedom to forget about how I look and can spend my time focusing on more important aspects of business and relationships.
I used to spend way too much time wondering if I was dressed appropriately for formal events or if the things I wore in daily life were making me look my best.
When I would be at a wedding reception, I used to look down at my clothes and wish I’d worn something else. Or I’d feel self-conscious about the cheap, cheesy pair of dress shoes I was wearing.
Now I get dressed with great care and then forget about what I put on as soon as I leave the house (with the exception of smiling every time I glance at my polished shoes).
Time in meetings should be spent focusing on the discussion, not on wondering if your tie is right for your shirt or if your shoes are “dressy” enough.
Free yourself from self-criticism by knowing you look good.
My confidence has skyrocketed
Being well dressed has given me the confidence necessary to go after the things I want out of life.
You shouldn’t have to think, “I would talk to that woman, but she’s so pretty and I look like a bum.” or “I would go after that promotion, but all the other guys are so much more qualified.”
When you’re well dressed, you’re presenting the world with the best version of you and you will feel that with everything you say and do.
Before improving my style, I had this inherent feeling that other people were better than me based on their appearance. I understand that this is far from a healthy way of thinking, but it wasn’t intentional.
Turn things around and let other people feel that way about you.
Taking responsibility for my appearance and learning how to dress appropriately has allowed me to become “me” and the same can be true for you.
I have a sense of control
While I can’t control everything that goes on around me, I can control the way the world sees me through the clothes I put on in the morning.
This was especially comforting when I struggled to transform my body the way I wanted.
Even though I was simultaneously improving my physique and style, my body was one resistant son of a bitch. I was controlling everything I ate and doing all the right things in the gym, but my results were slow at best.
The one thing I had power over was the clothes I chose to wear. I could continue dressing like the insecure teenager I felt like inside, or dress like the confident man I wanted to be.
Life likes to throw you curve balls. You can run into important business contacts on the street, get chosen for an impromptu presentation, or meet the girl of your dreams at any moment.
Since you don’t know what each day is going to bring you, exercise control over your body and what you show the world.
Being in control of your appearance will give you a feeling of power.
I have a newfound sense of pride
Unless you pay someone to shop for you and then lay your clothes out for the next day, becoming well dressed takes practice and patience.
I’ve spent years reading, experimenting, and generally obsessing over style. And as with learning any new skill, I’m left feeling a sense of accomplishment.
In the beginning, I was completely lost. I didn’t know how to put together an appropriate outfit to attend a wedding. I didn’t know what to wear out to the bar (usually erring on the side of douche-y).
I bought a lot of pieces that I never ended up wearing because I was so clueless.
But after a few years, I’ve learned so much that I can’t even imagine going back to the way things were.
It’s an incredible feeling to know where to spend your money and where to hold back, knowing what outfits are appropriate for which scenarios, and how to send intentional messages to those around you.
By putting in the work, you’ll reap the rewards and feel the associated pride.
I have an outlet for self-expression
I can’t sing or dance. I don’t paint or do spoken word or local theater. Instead, my medium for self-expression is clothing.
I’m able to express my mood (serious or light-hearted), personality (easy going and creative), and personal taste (simple and timeless) with each new day and each piece that I wear.
Through my clothing choices, I let the world know that I prefer functional, elegant design and take pride in owning quality pieces that I love, maintain, and help get better with age.
You’re sending a message to people with the way you present yourself. In turn, they’re using that message to formulate an idea about who you are before you even speak.
Use these inevitable assumptions to your advantage.
It’s become easier to meet people
Nice clothes are a great conversation starter. One thing that truly helped me overcome shyness and insecurity was being forced to have a conversation with every stranger that came up to compliment my clothes.
Even in the same week, I can see how being well dressed draws people to me.
I have a pretty good laboratory at my disposal since I live in a highly populated area and I’m surrounded by people as soon as I leave my apartment.
If I wear shorts and a t-shirt one day, I may not talk to anyone. If I’m dressed my best, people come up to compliment me and ask for directions or the time like they don’t have a smartphone in their pocket.
In much the same way that people want to be around beautiful women, people naturally gravitate toward a well dressed man.
When your style of dress is mediocre, you tend to fade into the background. It could even be intentional – sometimes insecurity can make you want to be invisible.
But you don’t have to be invisible. Get out in front of the world and show them who you are.
I’ve overcome my fear of public speaking
I’ve always been more content to listen rather than talk. But when I returned to college in 2009, professors always assumed that based on my image, I was comfortable with being the center of attention.
More times than I can count, I heard, “What do you think, Nate?” or “Would you mind coming up here to demonstrate this to the class?”
I was absolutely terrified to get up in front of my classmates, but I did my best to play it cool and went through with it anyway. It wasn’t easy at first.
Apparently no one noticed that I was shaking like a leaf because they made this singling out a frequent occurrence.
But after being made to get up in front of people so many times, I finally got to a place where public speaking didn’t make me want to dissolve through the floor.
I’m not exactly ready to give a TED talk, but the idea of presenting in front of a group doesn’t frighten me or deter me from professional or academic events any more. It’s pretty liberating.
What changed from the outside
Bosses held me in higher regard
As I improved my style and grooming, those above me on the corporate ladder always seemed to assume that I was more organized, motivated, and capable than my co-workers, even when that wasn’t the case.
It got to the point where upper management thought so highly of my competence, they stopped giving me guidance all together. I’ve even been left without instruction during my first days at certain jobs.
Employees who remind bosses of a young version of themselves are the ones who receive raises and promotions.
Since the boss didn’t get to the top by skipping haircuts and wearing a hoodie to work, maintaining a sharp appearance can help you advance in your career.
People ask for my advice
Everyone seems to want my opinion on a situation these days.
Friends and family members who used to ignore my well-intentioned and useful advice, now listen to what I have to say with greater enthusiasm.
It doesn’t have to be style related. People seem to want advice on fitness, personal finance, relationships, and purchases.
When you’re well dressed, you present the image of success. And who better to ask for advice than a successful person?
I get more attention from women
Not that it matters since I’ve been off the market for many years, but I’ve noticed a significant increase in the amount of attention I get from women.
I was always regarded as a “cute” boy in middle and high school. But after graduation and starting to work in construction, my body went to hell and my style was stagnant.
I went from getting love notes from many of my female classmates and compliments from complete strangers, to being largely ignored by women for a span of four or five years.
Once I started working on my body and improving my style, I noticed a drastic increase in attention from the ladies. So even as the same guy with the same face, living in the same city, my experiences were like night and day.
Women often view well-dressed men as being more successful and as better partners – more responsible, stable, considerate.
The underlying implication of being put together is that you have the time and resources to take care of yourself.
My concerns are heard
Customer service employees used to treat me like I was a dirt bag trying to scam them for free shit when I would voice legitimate concerns about their product or service.
These days, service reps are always happy to upgrade my hotel room, offer discounts on future purchases, or send a free drink my way to smooth over any wrong on their behalf.
I’ve been on the other side of the counter, as well. When I was working at a downtown hotel, I definitely recognized a few patterns.
It seemed like some people were just there to make a scene for the purpose of getting their $62 valet parking fees comped. These people were more often than not, poorly groomed and dressed.
Anytime well dressed people came up to me with a concern, usually in a respectful manner, I was ready to listen and eager to correct any issues.
Of course, your approach plays a major part in customer service, but it’s really helpful if they don’t have their guard up before you finish your first sentence.
I’ve been asked to lead more often
When a decision has to be made within a group, people look to me a lot more now than they used to.
Many of the qualities that are projected by a well dressed man also align with the qualities of effective leaders. People can’t help but to assume that if you’re so put together, you’ll be able to guide them as well.
I even see it in situations as commonplace as walking around with friends. When someone raises a question like “which direction should we go?” or “what should we do for lunch?”, I’ve noticed people’s eyes turning to me more than they used to.
When you step up your style, you may be asked to lead more often. Take your chance.
People are sometimes intimidated by me
I can see that some people are initially hesitant when I approach them now. The cause is most likely a combination of my height, clothing, and beard.
When we see well dressed or attractive people, our mind starts to raise questions and make assumptions:
“He looks really successful – he’s probably an aggressive jerk.”
“Must be nice to be born into a rich family.”
“He probably thinks he’s too good to talk to us.”
But once I start a conversation with a new person, they usually seem relieved and quickly become more comfortable as they realize I’m not arrogant or ultra aggressive, as they may have imagined.
I think this actually works to my advantage.
When people assume that you’re going to be a dick, and you prove them completely wrong, they’re a bit embarrassed for making such a hasty judgment and feel indebted to you to make up for their misled mental accusations.
Sales staff give me more attention
But they’re also more courteous when I tell them “I’m just browsing.”
I used to feel really pressured to buy things just to prove that I had the means. Sales staff actually use that as a tactic. They treat you like shit and in turn, you make a purchase to become part of a “club.”
I remember a time when I was in my dirty mechanic clothes on my lunch break.
I used to browse car lots, fully intent on purchasing a car (with the savings to do so easily), but the salesmen couldn’t even be bothered to come talk to me.
Now, I can walk into stores that sell $350 neckties (I don’t actually buy them, of course) and get treated with dignity.
In the minds of salesmen, poorly dressed people can’t afford to shop in their stores and are wasting their time. Meanwhile, well dressed men can afford to shop in these stores, but simply may not see anything they want to purchase.
Dealing with negativity
As you can see, it becomes difficult to pinpoint the origins of all of these positives that will result from improving your style.
Does dressing better give you confidence or does being treated better because of your appearance get the credit?
Regardless of the origins, these positives have a snowball effect. The better you dress, the better people will treat you, the more confident you’ll feel, the better people will treat you, and so on.
But not all the feedback will be positive.
Keep in mind, your efforts to dress better may be met with some resistance. Much like the way fast food junkies will poke fun at anyone making healthy eating choices, the guys in baggy tees, sports gear, and backwards caps may give you some grief.
Bettering yourself will always invite criticism because, in the minds of others, this means you think your way is better. Some people will view your transformation as a critique of the way they’re living and presenting themselves.
They will become defensive. They may criticize your choices. They might try to diminish your accomplishments.
But don’t let any of that get you down.
You’ll find that these shallow criticisms only come from people who don’t matter and those seeking to drag you down.
Anyone of importance will realize the effort you’ve made and be excited for the good things coming into your life.
7-Day Style Challenge
I hope I’ve been able to demonstrate the benefits of being well dressed.
But I don’t just want you to take my word for it. It’s time to put what you’ve learned into action.
Ever notice how you feel awesome and can’t wait to get in front of people when you’re wearing your favorite shirt or best fitting pair of jeans?
I want you to have this feeling everyday!
Starting next Monday, I’d like you to dress your best everyday for one week.
During this week, you should wake up earlier than usual, shower and groom first thing, and dress to the best of your ability.
I don’t mean to imply that you must dress in a suit and tie everyday.
It’s perfectly acceptable to dress in a casual manner if that’s what aligns with your occupation and lifestyle. But do it in the best way you can.
Feel free to blatantly mimic a look you saw online, if you’re drawing a blank on where to begin. I just want you to get the experience of being well dressed everyday so you can see how it’ll improve your life.
During this week, you should make an effort to be more social than usual. If not already part of your routine, you can:
- Go out for a drink with a friend and see where the night takes you.
- Talk to an attractive woman at the grocery store to test your confidence (perhaps ask her for a simple dinner idea to open the lines of communication).
- Spend a day working or reading in a coffee shop and see if you can make friends, get someone’s business card/hand out one of your own, or land a date.
- Engage in one other social activity that is out of your norm (bowling, billiards at a pool hall, a whiskey tasting, museum trip, a concert, a local festival, etc.).
At the end of the week, reflect back on the looks that made you feel your best and most confident.
Evaluate what benefits you took from just 7 days of dressing better. Do they line up with anything I experienced and described above?
Let me know your reactions to the challenge in the comments below!
Once I decided to make a change from the outside, great things started to happen on the inside.
While this might not be the right approach for everyone, it was the catalyst I needed to set everything else in motion.
Similar to the way that smiling, even if you’re mad, actually makes you feel happy, dressing better can greatly enhance your life in the same backwards manner.
It can be extremely difficult to change from the inside. We all have different genes and experiences that shape the way we think and feel.
So if you’re struggling with becoming the man you want to be, take advantage of an easy fix.
If it’s time to shed your old skin and become a better version of you, don’t fear the change, embrace it.
Never be afraid to reinvent yourself!
All the best,