Welcome to Module 6: Your Personal Style: How to Break Away From Boring and Try New Things, Without Looking Stupid

In the previous Module, you learned:

  • Creating 3 Go-To outfits for common situations (weekend casual, work and business events) will give you a starting point to help you create an endless amount of outfits depending on your needs.
  • Quickly identifying if a piece of clothing is too casual or too formal is easy when you keep a few rules of design in mind.
  • Creating outfits for your Style Scale will get easier as you build out your wardrobe more. You can get far in the early stages by focusing on the essentials and creating a few Go-To outfits. When you’re ready, you can pull out The Style Scale to create appropriate outfits for situations you find yourself in.

In this final lesson, I’ll show you how to make great style your own by developing your Personal Style. 

Remember what we said in the beginning of this course. Personal style is actually pretty advanced. Just like Chef’s learning to cook, you study the classic “recipes” then learn how to put your own riff on it.

In the previous Modules, you learned how clothes should fit you. You learned how to build a classic, essential wardrobe and create infinite outfits from that. Today, you’re going to finally learn how to stand out from the crowd and truly make your style personal.




trend11. A Modern Take of a Classic Design

Men are a lot more picky when it comes to what they wear than women.

This is why men’s clothes tend to have the same basic shapes and structures, but get updated in colors and details. The above is a perfect example of a modern interpretation of a classic piece, in this case, the bomber jacket. The trendy version of the bomber isn’t that wild when it comes to the colors or details.

But updated classics can be a lot crazier. It all depends on how far you want your Level 3 piece to go.


2. A Color Variation That Magazines or Blogs Consider “In This Season”

Nobody likes it when something get’s too popular. Just like that annoying song that plays on the radio every minute during the Summer, come Fall people are begging for something new.

The most common changing trend from season to season are colors. This is an easy trend to incorporate into your wardrobe. Usually, the design doesn’t change much outside of the color, so you won’t feel uncomfortable adding this piece to your wardrobe.

This is one of the few cases where you should listen to magazines like GQ and Esquire on a trend. They’re generally on point when it comes to trends in styles and colors.


3. An Original Design From A Designer

A perfect example of something original from a designer are graphic t-shirts.

We’ve stayed away from graphics for the most part because men can often overdo them in their wardrobe. And nothing screams “I’m still in high school!” like a wardrobe filled with graphic t-shirts. But graphic tees and sweatshirts are fun from time to time. Especially in hotter weather, it’s an easy way to make your outfit a lot more interesting when you’re only in a t-shirt and shorts.

Other examples might be prints a designer developed for their button-up shirts, or a completely wild clothes not found anywhere else.

One of my favorite examples of this is the technical design company Acronym, who design some wild spy/ninja clothing.


4. “Hot Trends” That Everyone Wants

Similar to colors, every so once in a while a piece of clothing will explode in popularity and become “hot”.

A recent example of this were tailored sweatpants. You can often see these hot trends when it comes to shoes and sneakers.

I always have a love hate relationship when it comes to this specific trend. While I’m always excited for new and interesting products, you can definitely look like a lemming following the crowd. I highly recommend you proceed with caution when it comes to these kinds of trends.

Where to Shop for the Latest Trends?

You can find trendy items even at places like J.Crew, which has a special section called “In Good Company” where they stock other brands that are sometimes a little bit more fashion forward.

Keep in mind, when it comes to trendy clothes, you will often be paying a premium for the “new/wow” factor. With that in mind, here are few other favorite stores of mine that stock trendier clothes:

Mr. Porter
Hypebeast Store
Carson Street

Where to Find Out About the Latest Trends?

This is where traditional fashion media is a great resource.

My favorites are:

Mr. Porter Journal

Last Bits of Advice When It Comes To Trends…

If you recall the “Levels” back in Module 3: The Essential Wardrobe Checklist, trends fall under “Level 3”.

That means if you have yet to build a solid Level 1 wardrobe with a few Level 2 color variations, it’s best to wait before you start venturing into trends.

A good rule of thumb when it comes to stocking classics vs trends? I’ll go with 75/25 .

75% classics. 25% trends.

That means one trendy (Level 3) piece for every three classic/color variation (Level 1 & 2) piece.


Formal & Refined…with a bit of hidden rocker (via The Sartorialist)

Recall our burger analogy. Classic style is like a classic burger. All-beef patty, american cheese, ketchup and sesame seed bun. Timeless.

Now it’s time to put your own riff on it.

Great Personal style is all about authenticity. Men become fashion victims when they hop from trend to trend. We learned how to avoid this by:

  • Sticking with a primarily classic wardrobe
  • Restraint: We add just enough elements to our look to make it interesting

Now, it’s time to take it to the next level using these techniques.

The #1 Way to Boost Your Personal Style: Contrast

Contrast is what makes something a lot more interesting. Like adding salt to a cookie, or making a Superhero movie for adults, cursing, gore, sex and all!

Take a look at the image above of the man with a refined formal style wearing a classic rocker leather jacket underneath his coat. A great example of contrast of two different styles: formal + edgy.

His look is saying to the world “I’m grown up, but was in a punk band for most of my life.” You immediate want to know his story.

That’s the power of personal style. You not only stand out, you will draw people in. Contrast, done right, evokes curiosity and interest. 

Some ways to use contrast in your style:

  • Contrast between styles/genres: Classic Menswear + Rock. Streetwear + Military. Formal + Sneakers
  • Contrast in color: All black + pops of color. All neutrals + pops of color
  • Contrast in fabrics: Wearing a rugged leather jacket with a soft cashmere scarf
Photos via The Sartorialist

Add a Pop of Color

Adding a pop color kills two birds with one stone.

  1. You add more color to your outfit
  2. Make your style a lot more interesting

The key is to not overdo it.

It’s called “pop” for a reason, it should contrast with the rest of your outfit.

Luckily, we established a base of neutral essentials that make this dead easy. You can make your pop as simple as a pair of gloves or scarf, or go bold and do something like a pop pants (like the gentleman above, left.)

Socks are the perfect pop color gateway

My recommendation, start small. A colored beanie, scarf or even socks with a mostly neutral outfit are just the right amount.

Designer Mark McNairy always sports a baseball cap
Designer Mark McNairy always sports a baseball cap

Tap Into Your Interests and Life Story

It’s called personal style for a reason.

If you want true personal style, inject some of your personal interests, personal stories and personality in to your style.

Always wore baseball caps growing up? Wear them (see above).

Listened to an unhealthy amount of Nirvana as a teen? Wear a Nirvana t-shirt.

Ring by Mark McNairy
Ring by Mark McNairy

I love sneakers and grew up collecting them, you’ll find me in sneakers 90% of the time. And while I’m not big on men’s jewelry, I’ve been known to sport a ring from time to time. (See above)

Baseball teams. Colors you love. A logo sweater from the college you went to.

Blend them into your looks seamlessly by using what we learned in the previous modules: “Levels”, The Swap Trick, 75/25 and Contrast.

Action Step: Brainstorm and list some of your personal interests and life stories, and see how you can weave them into your style. Some sample questions to get you started.

  1. What is your favorite band? (Vintage band t-shirt or style inspiration)
  2. Where did you go to college? (College sweater)
  3. What’s your favorite sports team? (Team hat)
  4. What fictional character’s style do you admire? (For example: Daniel Craig as James Bond in Casino Royale)
  5. Have you been on a trip that inspired your style? (For example: Men in Japan who are into Americana style)
My Style Inspiration Pinterest Board

STEAL, STEAL, STEAL: Grab Inspiration From Other Stylish People

I come from the school of thought that nothing is truly original. Everything’s a remix.

The iPhone wasn’t the first phone (or smart phone for that matter). In-N-Out burger didn’t invent burgers.

There’s nothing wrong with taking a good idea so long as you add too it and make it your own.

I’m constantly looking at websites, saving them to my Pinterest board or hard drive to see interesting combinations, styling, color mixing, etc.

Two Problems: One, he didn't steal from more than one place. Two, he stole a terrible outfit.
Two Problems: One, he didn’t steal from more than one source. Two, he stole a terrible outfit.

The trick is to “steal” from more than one source. Don’t only draw inspiration from Steve McQueen, or Miles Davis (both favorites of mine). If you constantly draw inspiration from one source, you end up looking like you’re playing Halloween.

Take a little bit here and there, combine them, add a little bit of yourself on top. At the end, you’ll end up with a completely original style.

Some of my favorite places to steal draw inspiration from:

The Sartorialist
Mr. Porter (Take notice how they style outfits in the store)
My Pinterest Board on Style Inspiration (Bookmark this as I’m constantly adding to it)

ACTION STEP: Review the links above. Start collecting and pulling images of men with style that inspires you. Don’t think too much about it, trust the instincts you’ve developed over the last few modules.

Save them in a folder to review.




Now, before I leave you to build out your wardrobe and develop your personal style, I want you show something a little advanced. If you’re still working on getting your fit down, or building your essential wardrobe and mixing colors, do not try this yet. Proceed only if you have your Go-To outfits on your Style Scale.

There’s that classic saying, “Learn the rules then break them.” And I’m going to show you how to “break” the number 1 rule when it comes to great style: Fit.

I know, shocking, right? But like everything we’ve learned in this course, there’s a right and wrong way to do something.

The two photos above are beautiful examples of men breaking the rules of fit. On the left, we have a guy that’s wearing a coat that’s a few sizes too large on him. On the right, a man in a pair of pants with a low crotch and “baggy” fit.

Take a minute: Analyze both photos. What do both photos have in common besides the oversized clothes?




Did you say “The rest of their outfits fit”? (Yes? GOOD!)

This is a PERFECT example of a few techniques we learned earlier in this lesson: contrast and restraint


Recall this photo.

Let’s ignore how bad this outfit looks overall on Kanye West and the poor kid. Let’s focus on the fit.

Notice how the only thing that fits are the pants at the very bottom layer (We won’t count the shoes or the bag).

Everything else is oversized.

Remember our “Cut in Half” rule in Module 2. Both Kanye and the Kid look like stumpy munchkins. There’s just too much fit rule breaking in this outfit. Too much contrast, not enough restraint.

The two looks in the first image work because the rest of their outfit work. By breaking the fit rule in just one piece, their style comes off as relaxed and effortless.

They just look damn cool. 

So if you want to break the fit and add an extra element of effortlessness to your look, some rules to keep in mind:

  1. Don’t go too big: Restraint. 1 size larger for a piece of clothing is a great place to start, 2 is pushing it. 3 is too much.
  2. Think opposites: Contrast is key here. If you want to wear oversized pants, your tops must fit properly. If you want to wear an oversized top, your pants should fit properly. Oversized coat? Make sure your entire outfit “inside” fits properly in comparison to your outerwear. (Note: The only exception to this rule – don’t wear an oversized outfit with a properly fitted coat. That’s just weird.)
  3. Relax: The point of breaking a rule is to give off a “I don’t give a fuck” attitude. You’re breaking a rule on purpose, and if you followed all the recommendations here, you’re doing it with even more style. So relax. Recall the quote from Sir Hardy Amies in the beginning:

“A man should look as if he’s bought his clothes with intelligence, put them on with care and then forgotten all about them.”




  • Your style can be amazing and timeless by sticking to Level 1 and Level 2 items. But if you want to break away from boring and stand out, developing a Personal Style is the key.
  • Trends are a quick and fun way to take your style beyond basic. To avoid becoming a fashion victim, you want to remember the “Level” rules of building a wardrobe, and aim for a 75/25 ratio of classics/trends.
  • Making our style more personal is what truly makes personal style. We do this by drawing inspiration from style we like, digging and sharing parts of our pasts and interests, and experimenting.


  1. Brainstorm how you can inject more of you into your personal style by listing out your interests and past experiences.
  2. Review the links I shared to get inspiration for great men’s style. Save images you like into a folder for later.
  3. When you’ve build a solid Level 1 and 2 wardrobe and want to explore trends, review the material on adding trends to your wardrobe intelligently. Explore the links to websites provided.



Congratulations on completing the course. And thank you for being part of the beta program.

Remember, as a beta member you get lifetime access to this course and all of the updates.

What’s next:

As we talked about in the beginning, rebuilding your wardrobe and developing your personal style is a process. While the course is finished, many of you will continue developing and using the lessons you’ve learned in the weeks to come. Be patient, review the materials, and most importantly have fun.

For those that are a little behind, don’t worry. I’m here and the group is here to help you catch up.

From this point forward, I’ll be posting about new material and any changes to these modules etc in the Facebook group, and via e-mail.

As you re-review this material, please don’t hesitate to make any requests you think should be added.

Remember guys, I’ll be opening this up again soon to new students. As the group gets larger, I’ll have less time to give you one-on-one attention. So this is definitely the time to take advantage of it!

Thanks again. I’ll see you in the Facebook Group!