Simple Clothes Better Style

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.


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!