Welcome back! I’m excited to talk to you today about how to live a better life through dressing more intentionally and to give you some concrete examples of what your wardrobe can look like by adding in just a few key items.

If you guys haven’t seen my first post talking about this – make sure to click the link HERE and go check that out.

Like we talked about last  time, I know it ca feel a bit odd to realize that your whole life can improve by dressing better, but it really is one of the best ways to start to overcome mediocrity and complacency – two of the biggest problems the average man in the 21st century experiences.

Click Here to Watch the YouTube Video: Simple Clothes Better Style

Click Here to Watch the YouTube Video: Simple Clothes Better Style

The Opportunity

If you feel like you’re in a rut in your life, or you’re all but invisible to the people around you, or you’re more tolerated than respected, or you’re missing out on opportunities to do bigger and better things with your life – improving the way you present yourself to the world can be the kickstart you need.

What I’m going to give you today are a few simple things to get you started. This is advice that you can take right now and start seeing improvement – it’s up to you to act on it though.

Now in this post I’m going to give you three full outfits that can look great.

A Bit More Rugged

Let’s say you want to look well put together but not like you live in an office all day.This first look combines some elements that have a Rugged history, without making you look like a wannabe lumberjack.

Here’s a simple way to do that – start with a pair of dark jeans, some casual work boots, a henley, and a military style field jacket.

The big thing that will make or break an outfit like this is how it fits. You may like yours a bit fuller or even on the skinny side – doesn’t matter as long as it fits well and each item is consistent. You don’t want to wear a super tight shirt over a fuller cut pair of jeans. For this look, everything I have on is moderately slim – which works for my build because I’m more on the slender side.

Each item in this outfit has origins in workwear. These are not things that were worn by city-dwelling gentlemen who never did a day of hard labor. You can embrace that ethos by letting them get nice and beaten up, or counter it by taking good care of them and making sure they’re always fresh and clean.

Both approaches work great and both tell a slightly different story – so experiment and see which you like better.

Better Than a Suit

Ok let’s move onto a second look. This is one that’s great for you recovering suit-only guys. It’s still more dressed up than what the average man in the West wears, but it’s not so far removed that it will start to negatively affect your and your potential.

Split that suit up into separate pieces (the key to doing so is cloth that has some texture to it). For this I’m wearing a pair of cotton chinos and a flannel navy jacket. Ditch the tie and swap out the dress shirt for a polo. Cap it off by wearing a pair of suede chukka boots.

Notice that the fit in this outfit is a lot fuller than the first one. It’s a great reminder that there is room for fit preferences – full, slim, or skinny – without saying one fits well and the other doesn’t. By knowing about where things should sit on your body, you’ll have much more freedom to choose your fit preferences.

If this still looks a bit more dressed up than what you’d like, all you have to do is ditch the jacket (or even swap it out for the field jacket from the first look) to bring it down another notch.

Back to Basics

Let’s take it way down to the basics for look number three – the ubiquitous T-shirt and jeans.

We’ll use those same jeans from look one, a simple, well-fitting T-shirt, and a pair of classic sneakers. That’s it.

What can make something like this so effective is its simplicity. The principles of fit are followed – notice how the shirt is neither too tight nor too baggy. It’s simple – there are no logos on the shirt, no bright colors, nothing that’s going to overly stand out from the rest of the look. And lastly, each piece is classic. If you were to swap out the Chuck Taylors for the pair of Sketchers you see Baby Boomer grandpas wearing at the mall, the whole look would be ruined. By focusing on proportions, colors, and textures that have been worn for decades and don’t draw too much attention you can keep a simple look working for you as long as you want.

Want to dress it up a bit? Upgrade that T-shirt to the polo from look two. Even more? Add the sport coat on top of it.

The beauty of owning simple, well-made, versatile items like this is that they can all be swapped around with each other – giving you a ton of variety without having to invest into a massive wardrobe.

Two Responses

As I’ve presented this information to men in the past, I typically get two different responses – they’re either underwhelmed or overwhelmed.

So let’s talk about both of those.

To set that up though, we need to address something from the last video that can seem like a contradiction.

In that video I told you that dressing intentionally can help you conquer mediocrity and then proceeded to tell you that you don’t want to stand out too much.

Those can seem contradictory. After all, when you start dressing better it’s going to separate you from the people around you who don’t. It’s going to make them feel uncomfortable and you’ll probably even get some kickback from them.

This usually happens because overcoming mediocrity ourselves can often show the people around us that they’re not choosing to do so. And, in ego-preservation mode, they’ll choose to write off, ridicule, or resent your progress.

What you don’t want to do with your style is go from 0 to 100 in a day. The change will be too jarring. You’ll both feel and look like a fake and it won’t be putting you up above average, it will actually have some negative affects.

The trick is to get items that are one or two steps above what you’re currently wearing.

Take that first outfit I showed you as an example. No one is ever going to accuse you of being too dressed up or too fashion conscious if you show up wearing those items. But you’ll also look better than most men in Western civilization.

Unless you’re making some seriously drastic changes in your life – your goal should be to look like you’re a step above, not a step apart from the important people in your life.

If you’re feeling underwhelmed by these items you’re still in the mindset that dressing intentionally is dressing up. Yes, wearing a three-piece suit on a Saturday coffee date is going to help you stand out from all the guys who don’t – but it’s not going to be standing out in a positive way. You’ll look like a weirdo with no social fluency and you’ll miss more opportunities than you gain.

I’ve just given you ten items (with a few more snuck in there for good measure) that can take your style game from meh to awesome. Believe it or not, I have 25 more that I give my clients.

If you’re feeling overwhelmed,

I know 35 items can seem like a huge investment – and it can be. But many of the things I recommend are only appropriate for some men at one or two points in their lives.

If you live in Hawaii you don’t need to buy a winter coat tomorrow – but you will want one that looks great if you’re ever in London in February.

So it’s not as if all 35 need to be purchased tomorrow to get you living a better, more respected life.

The other question I get most frequently when presenting these Staples to my clients is,

How do I take this up a notch and start to inject my own personality into my wardrobe?

Which is what we’ll be addressing in the next post.

Conclusion

In the first post I asked you to leave me a comment letting me know how you believe your life will improve by dressing better. I love the comments and that you guys truly get that this isn’t just a shallow change but a pattern disruption that affects both how you see yourself and how others perceive you.

Well now I want you to tell me how you would take these simple items and wear them. What would you pair together that I didn’t show in the video. Would you prefer a fuller cut or a slim one? Where would you wear each of these three outfits and how much are they an improvement and what you currently have in your closet?

We’ll be diving in a little more on how to tell a story with your clothing on the next post and I can’t wait to talk about it with you guys!

Can dressing more intentionally really improve your life?

Do clothes make the man?

Does dressing better mean you have to wear suits all the time?

I get questions like this all the time and the answer is that clothing is just like any other tool.

Did the lightsaber make Luke a Jedi? Was Arthur king because of Excalibur?

Click Here to Watch the YouTube Video: Better Style Better Life

Click Here to Watch the YouTube Video: Better Style Better Life

The Hero’s Journey

I want you to engage in a little thought experiment with me. Take a moment and think of your favorite hero from your most favorite story.

Now think about why that story is so compelling. Why do we as men, get really interested in hearing stories about men who start off as normal, regular guys and are faced with a problem.

What makes them heroes is that they overcome the problem. They defeat the enemy, conquer the foe, or take whatever the problem is and vanquish it.

That is why we are so addicted to these stories. Because we see these men, whom we think might be like us, and we see them do hard, difficult, and worthwhile things.

One of the things that every hero receives as part of his heroic journey is a tool or set of tools to help him along his way.

Think about Harry Potter and his wand, Luke Skywalker and his lightsaber, or King Arthur and Excalibur.

Part of the experience is receiving the tools which help them overcome the problem and become the heroes they were destined to be.

What’s Your Heroic Journey?

Think about what this is in your own life.

If you’re like me, you don’t have any huge, world-destroying enemies. Most men don’t. Most men throughout history haven’t.

But that doesn’t mean that we don’t have enemies, that we don’t have problems, that we don’t have things we need to conquer in our lives.

If you’re like most men – especially most men in the 21st Century, where our lives are relatively easy – then one of the biggest problems you need to conquer is either

Mediocrity

or

Complacency

Does that ring a bell for you at all? Do you feel like the challenge of your life is not becoming mediocre or average?

Do you want to be better today than you were a year ago? Do you want to be miles ahead of where you are in another five years?

I know I certainly do and I think most men feel the same way.

We have an innate desire to take the Heroic Journey and apply it to our own lives – even if our problems and enemies are much more subtle than Voldemort or Darth Vader.

Just like the heroes of stories, I want you to think about some of the tools you can have that will help you to conquer mediocrity.

Whatever the antithesis of average looks like for you – be it a big, fulfilling career, a family who loves and adores you, the opportunity to travel across the globe and have epic adventures, or any other definition of a meaningful and fulfilling life – think about that.

Whatever overcoming mediocrity looks like for you, one of the tools you can have in your kit, is your wardrobe.

Dressing well isn’t just a hobby. It’s not simply for guys who think suits are really cool or those who have the money (and inclination) to build up a massive and detailed wardrobe.

#dressintentionally

In fact, that’s why I tell people to dress intentionally as opposed to dress well. The phrases “dress well” or “dress up” have a particular connotation of wearing more formal clothing. They make us think that the only two options are either to dress casually and sloppily or to dress up and be uncomfortable.

It’s a totally faulty line of reasoning and it makes millions and millions of men miss out on an easy opportunity to improve their lives.

And yes, dressing more intentionally can absolutely improve your overall life.

It can help you land that job, command a room, and connect with the woman of your dreams.

As I’ve helped thousands of men dress better over the last five years, I’ve learned that most of us want the same thing – to look and feel great without standing out too much.

Sure there are plenty of guys who really want to draw attention with their clothes (and I’m happy to help if that’s your goal) but most of us don’t want to dress flamboyantly or ostentatiously. In fact, we don’t want people really thinking about our style or clothes at all.

We just want to look good, respectable, and confident and wear clothes that don’t stand out – either negatively or positively.

One of the reasons I know that dressing up isn’t the same as dressing intentionally is because of how I personally learned the impact clothes can have. Do you remember how tough it is to be an awkward teenager? And not like the “I have the world all figured out because I’m a senior in high-school teenager” I mean seventh and eighth grade – when everyone looks weird, no one knows if they’re more of an adult or a child, and your identity is starting to become more dependent on your friends than your family.

Well I spent those years attending a school that had a uniform. The problem was that my friends at home and I were more interested in BMX bikes and punk music than Latin or reciting poetry. And when my friends would see me in my grey slacks, white shirt, and blazer, I quickly became an easy target for teasing and was soon the runt of the pack.

The clothes weren’t the only factor – my lack of confidence, fear of rejection, and small stature certainly contributed but I wasn’t really singled out until I was seen in slacks and a jacket.

As good as that experience was for me and as much as I wouldn’t trade it in for anything else, it was certainly difficult at the time.

I learned at an early age that dressing up can often have as many negatives as dressing down.

Which is why I now teach men to dress intentionally – whether that’s dressing up or dressing down.

I’ve been through almost every extreme – from wearing clothes that made me feel incredibly sloppy and self-conscious, to being known as the “style guy” (and dealing with how uncomfortable that can make most people feel), to finding the exact correct balance and knowing I can look great without having to expend a ton of energy (or money) or making other people feel overwhelmed or underdressed.

It’s Simple

There are ways to make even something as simple as a T-shirt and jeans look like something a movie start or action hero would where.

By focusing on things like fit, color and pattern, knowing a few key items that will look good on anyone and aren’t a quick trend, and learning how to express the right amount of individuality through clothing I’ve been able to help thousands of men dress intentionally and ensure their appearance is always an asset – never a liability.

I know you’re probably thinking that I’m going to draw some hard and fast lines in the sand. I don’t blame you. Those seem to exist in the world of clothing and appearance more than anywhere else.

But don’t worry. I’m not going to tell you that the only way to dress intentionally is to go buy three suits and never wear anything else, or that you have to throw away every single piece of clothing you own and pay thousands of dollars on a new wardrobe tomorrow.

I’m not going to make suggestions that – when you put them on – you walk out of the dressing room both feeling and looking like a complete fake and fraud.

What I am going to do, is give you some specific examples of how easy it is to dress better and start seeing improvements in your life immediately.

I’m going to show you how to understand what works with your body, give you suggestions for items that look great on any man anywhere in the world, and help you figure out how to move your appearance from simple and stylish to deadly effective.

Here’s what I need from you – whether you’re just graduating from cargo shorts and flip-flops or you already feel like you have this style stuff pretty well figured out.

Leave a comment below and tell me how you imagine your life can improve by dressing more intentionally. What advantages will it give you that you’re currently missing out on? What are your hangups and why are you not already dressing better?

I can’t wait to show you guys the next post and give you some real-life examples of simple outfits that can work well for anyone.

Do you remember in Fight Club when Tyler Durden goes on a nice little, nihilistic monologue telling his men what they’re not?

It’s one of the more famous quotes from the film.

“You are not your job.

You’re not how much money you have in the bank.

You’re not the car you drive.

You’re not the contents of your wallet.

You’re not your f*&#ing khakis.”

Well believe it or not, I almost entirely agree with him.

Click Here to Watch the YouTube Video: You’re Not Your Khakis

Click Here to Watch the YouTube Video: You’re Not Your Khakis

Nihilism

Before we talk about why he’s right, let me tell you what I don’t agree with (it’ll be quick).

Ultimately, it’s not all of the things he tells you you’re not, but what he tells you you are.

Part of that is because what Fight Club ultimately represents in a very Gen X version of the philosophy of Nihilism.

I don’t believe in nihilism. It’s not a philosophy I have any sort of affinity for because I believe in way bigger and better things than “we just become the rot and decay of the world.”

That aside – let’s talk about why you’re not your khakis.

You Can’t Buy an Identity at the Mall

The big problem with this – whether your identity is wrapped in the clothing you wear, the car you drive, the friends you have, or the contents of your wallet – whatever it may be – is that it conflates cause and effect.

What Durden is talking about is sad man who don’t have anything else to live for, nothing else to stand for, or anything else to believe in and so they base their identities entirely on what they consume. And that’s as far as you can get from true masculinity.

Because you should not be able to go and buy your identity at the mall.

This goes hand-in-hand with some of the things we’ve been talking about in other posts and videos. It’s trying to find the balance between Tribe and Taste, the balance between the group and the individual, or these two things that appear to be polar opposites and finding the right balance between them.

Obviously if you’ve been reading my stuff for a while you know I spend a lot of time talking about Tribe. How it affects your appearance and identity – and ultimately how it affects your reality.

But what I don’t want you to believe is that Tribe is the end-all-be-all because individualism is a huge component of masculinity. And the problem is if you’re all tribe and no individualism – that’s when you do become your khakis.

You shouldn’t be able to go out and just consume, purchase, or pick up who it is that you are as a person.

What that says about you is that you are not an active agent. You are not a man who goes out and creates things. You’re a passive consumer.

Your entire identity is not based on what you are internally; it’s not based on your Internal Presence that you project outward into the rest of the world; it’s based entirely on what the rest of the world projects onto you.

There’s a very big problem with that for us as men.

If you can’t project what you are, into the world around you you’ll never have influence. You’ll never have Presence. You’ll never be able to lead. You’ll never even be able to effectively follow. All you become is an automaton for other men who are more powerful, more capable, more fulfilled, and happier than you are.

Why We Become Our Khakis

I can certainly sympathize with why people feel this way or why this stuff ends up happening.

Think about what makes you different from anyone else in the world – I don’t even mean the world in general. Let’s just say the Western world.

What is it that makes you different from the other people at work, or in another city, or even in another country? Is it something big like the god you believe in (or don’t?), your ideas of what’s right and wrong, something that’s more internal like this is what makes a good man and this is what I want the world to look like? Is it really that different from everybody else?

Odds are, probably not.

In reality the only real differences between us and all the other “tribes” around us are superficial things – things like what we do for a living, the kind of clothing we wear, the programs we watch on TV, or the music we listen to.

The differences between tribes like cross fitters and powerlifters are not fundamentally big. They’re just superficially different.

Same goes for menswear guys who are really into streetwear or suiting. There’s not that big of a difference between us – it’s more of a matter of degree than kind.

The problem is when we live in a large, globalized world with no real concrete differences between all the different variations of tribes it becomes incredibly easy to just buy your identity.

There’s no meaning or underlying value to what your tribe is. You can change it as quickly and as often as your taste or your mood changes. There’s no loyalty, no honor, no desire for anything better. It’s all based on what you want to consume – which in turn, is all based on what other people are creating.

The Right Balance

What I want you to do as men, what I try to do for myself, what I try to instill in my children, and ultimately what I want to accomplish with this site is to help you understand what your core values are. What are the things you stand for? It doesn’t matter if they’re totally different from anybody else or completely in lock-step with someone. What are your core values? What are the things that make up your Internal Presence – that make up who you are as a man? And then, how do you use your clothing to project that out into the world?

You can’t do that if your identity is based on external, superficial things. You can only do that if it’s centered on internal, meaningful principles.

The mistake most men make when hearing Durden’s monologue is in believing that the clothing we wear shouldn’t matter at all.

Durden most likely was advocating for this, but that again falls into the trap of nihilism and how ultimately nothing matters.

Those who don’t subscribe to that philosophy can still get behind his speech, we just understand it differently.

The clothes you wear, the car you drive, and the contents of your wallet absolutely do matter and they can impact your life. They just don’t matter the way we think they do.

Rather than those being the cause and your identity being the effect, your identity should be the cause and all of those other things should be the effect.

As soon as you get those switched up and the balance is correct, there’s more consistency and congruency. You feel more authentic and project more authenticity. You’re more integrated with the people in your life who actually matter and care a whole lot less about those who don’t.

If you start by doing something internally, you have your moral code, you know what it is and your identity is based around that code, and you project outward from there – that’s how you lead a happy and successful life.

You’ll always be well-dressed (even if other people hate what you’re wearing).

You’ll be congruent with your tribe.

You’ll be authentic with yourself.

Your clothing and appearance will always be an effective tool to help you accomplish bigger and much more important goals in your life.

Sound Off

I want to hear from you!

Have you been through stages in your life where you were your khakis?

Where your identity was based on what you purchased, rather than your identity causing what you purchased and wore?

Leave a comment below!