Style Advice / October 12th, 2015

Level Up Your Style

I have a confession to make.

Ever since I was little, I’ve been an avid fan of video games.

Shocking isn’t it?

It’s the sense of adventure that does it. For a kid, it’s a difficult pastime to resist.

Although I don’t play as much as I used to, I still have a firm appreciation for video games and the level of escapism it provides.

If I had to choose a personal favorite, I wouldn’t hesitate to declare RPG’s the best video game category. Those of you not familiar with RPG’s, let me give you a quick overview. RPG is short for Role Playing Game and usually consists of a band of individuals coming together to form a party with the aim of fighting off some sort of evil threatening the world.

What makes RPG’s fun is the amount of customization and progression your characters go through in the form of “levelling up”. In short, the more you work on your characters skills, such as fighting enemies, the better you get. Earning enough experience will take you to the next level. In this example, a character that is level 20 would be a much better, more experienced fighter than one that’s level three.

This form of progression keeps the game interesting and gives the player control over how powerful and skillful he gets relative to the game. As you progress through the game, the enemies you fight become much more difficult and require you to have achieved a certain “level” to compete.

RPG’s are all about steady and continuous progression until your characters are the best they can be.

Surprisingly – All of this got me thinking about how men approach style.

Think of it.

In my experience helping men dress better, most clients come to me expecting to look great right off the bat without taking some time to research what sort of style is right for them.

In other words, they’re trying to be at level 10 when they really should be starting at 1.

That’s the wrong approach.

Instead, like true video game fashion, you must start with the default statistics and slowly build yourself up.

Now don’t be like most people and do one of the following two things:

  • Start from the bottom for a few weeks and then get overwhelmed and discouraged. This type of attitude results in giving up all together and going about your life as you always have.
  • Take a look at the first level and see how “easy or “pointless” it is and immediately jump to a higher level. Sadly, this also results in being overwhelmed and discouraged until your back at square one.

The good thing is you’re different.

You have been reading Timeless Gent for a while now and learned a thing or two about style.

You are going to start from level one and level yourself up until you’re a style icon.

My game of style consists of 5 levels. All facets of style are accounted for from the clothing you wear, the accessories you hold to the confidence within.

Game of Style

My game of style is not complicated but it does take patience and inner knowledge. Some levels will be hard for some and a breeze for others. Not a problem. Stick with each level until everything is achieved, never earlier. Your goal is to build a solid foundation that can support the additional levels later.

Now on to a description of the levels!

Level 1 – The Core

Level one at first glance doesn’t look like its style related at all. While I agree it may seem that way initially, as you progress you realize just how critical this level is to master.

The components to master in level one are:

  • Inner Values – What is it you fight for?
  • Identity – Who are you really?
  • Personal Style – How do you want to represent yourself?

Mastering this level is extremely difficult for some. I know it was for me. In fact I revisit this level from time to time not to rehash what I already learned but to ensure the things I mastered still make sense! As a mentioned, this level is the foundation to all others and a critical one to get right.

Now…let’s dive in just a bit deeper on each component.

Inner Values

As far as I’m concerned your life is all about choices and the reactions you make to events that happen in your day-to-day.

Most of your reactions stem from a deep emotional connection, either positive or negative you feel towards it.

These reactions are your key to discovering your inner values.

Let me give you an example.

A girl who you find highly attractive walks right up to your friend and strikes up a conversation. As the minutes roll you notice their body language become more intimate. There is no telling where this interaction will lead.

What sort of emotions rise from this random encounter in front of your eyes? Are you happy for your friend? Jealous? Indifferent? The answer to this will give you insight into a potential inner value.

Being truly happy for your friend can depict friendship as a value that’s important to you. On the contrary, being jealous could clue you in that being desirable is something that’s very important in your life.

The goal is not to be critical of yourself but just learn and soak it all in.

Perform this step with every aspect you can think of. When you have tallied a list. Gather and write down 5 that are the most important to you.

Your list can look something like this:

  • Family & Friends
  • Honesty
  • Power
  • Growth
  • Elegance

Once your list is in place, try to put a word or picture that represents it well to YOU. Don’t worry what others are thinking, if it makes sense to you then you are on the right track.

Using the example above, here is how this will look:

  • Family & Friends – Brother
  • Honesty – A Handshake
  • Power – Money
  • Growth – A Mountain
  • Elegance – A Mercedes Benz

Now before moving on, try to come up with a connection between the five things. It could be anything. In my opinion, the 5 points mentioned above sounds a bit like luxury. What does it represent for you?

Now on the next step and figuring out your identity…


Sure, let it out. I know that thought just creeped through your mind.

“Isn’t my identity and inner values the same thing?!?”

Well, in a sense they are…but not really.

Your inner values are parts of your identity but not the full thing. I would say your core values make up 50% of your identity.

Instead, your identity looks something more like this.


You are who you are based on so many factors.

Your thoughts play a critical role along with your goals, regrets and many other things to make up your unique identity.

What exactly is your identity? Here’s what I want you to do to find out. Look at the diagram above and take a look at how I weighted each of the criteria. Do you agree or disagree with the importance I applied for each? Now do your own! Draw out something similar and weight each criteria in a way it fits you as perfectly as possible,

Now that you have your completed diagram, put a few examples in your life that describe each specific area. As an example, you may put “retire by 50” as a goal and for achievement as “getting promoted to management at your company.”

This completed diagram coupled with your inner values should give you a good indicator of your identity.

Congrats on mastering this difficult part of level 1, now we can get into some fun stuff.

Personal Style

So you know what your inner values are and discovered your identity on top of that. Great stuff.

Now you have the daunting but fun task of discovering what your personal style is.

Your personal style is all about detailed keywords that describe you now and more importantly…depict who you want to be.

All you have to do is come up with words to describe your ideal style. To kick-start your own list, I have provided a very small selection of attributes you can leverage and build off of:

  • Sophisticated – Considered more of a refined style. Someone who sees himself as sophisticated in his style usually dresses in a way that’s “tried & true”. A safe but great style.
  • Elegant – A high quality, luxurious style using more safe colors and patterns. Timeless and classy
  • Innovative – A man who enjoys experimenting with new looks and garments to come up with completely new styles. Someone who innovates is not afraid to try new types of materials and incorporating then into their existing wardrobe.
  • Modern – The modern look takes what works from classic and timeless styles and introduces new details such as fit and construction. New take on classy.

Now how does your list look like? Remember – The shorter the list of words describing you and your style, the more personal it will be to you.

With all that complete, it’s safe to say you have a pretty good understanding of yourself. You have now leveled up.

The next section is going to take a more hands on approach to your style. When your ready….please proceed.

Level 2 – The Building Blocks

Given its core components, many men either start their style journey here or (no joke) even higher.

To be honest, you could do much worse than starting at level two. It’s a level, when mastered will leave you ahead of 80% of other men when it comes to looking good.

The reason why is that each of the three components as a bundle can make you seems like a superstar.

These three components are:

  • Foundation Clothing – Garments that will be your bread and butter
  • Grooming – Having great hair and skin
  • Skill Building – Being Able to be good at what you like to do

The problem for men jumping right to level two is they don’t truly know who they are. You can build a great wardrobe and have the best hairstyle, but it most likely will be based on the latest fad or trend.

Build your own unique style.

Foundational Clothing

No matter what your style is, great clothing matters.

With your knowledge uncovered from the challenges of level 1, you can begin to build out your wardrobe.

BUT! Before you begin, I do have a few simple rules for you to follow:

  • Purchase quality over quantity any day of the week. I don’t care that cheap dress shirts is 3 times cheaper. You want clothing that will make you look and feel good while lasting a long, long time
  • Don’t purchase your fundamental wardrobe all at once. Style is an investment and you should treat it as such.
  • Resist the urge to buy clothing that strays too far from the list below. The key to all of this is versatility. Buy great clothing that will give you plenty of options.

Now I present to you your shopping list

  • One (1) Navy Blue Blazer
  • One (1) Charcoal & One (1) Navy Suit
  • Two (2) Dress Shirts of Each: White, Blue & Pink
  • One (1) Pair Each of Denim: Blue & Black
  • A Few V-Neck White T-Shirts
  • A Few Cashmere Sweaters
  • One (1) Pair of Khaki Classic Chinos
  • One (1) Light Grey Cardigan
  • Various Shoes in Black & Brown
  • One (1) Charcoal or Camel Colored Pea Coat

This list may look boring but it works for many environments, skin tones and hair types.

Those reading this who work outside of the office thinking they don’t need to dress formal, don’t sweat it! All men should have the privilege of owning a suit other than black. Heck – I wear suits without a tie hanging out with friends on a Friday night.

Transitioning is a breeze with the selection as well, easily going from casual, to business casual to formal by adding or subtracting a few layers.

So after a few months, you finally did it. Your foundational wardrobe is complete. You now have to improve on a few more states by tacking another direction entirely.


Those of you at level two care about style but may have a hard time grasping the overall scope of it.

Men tend to think style is strictly what you wear and fail to realize that their skin and hair help form the entire physical picture.

Let’s examine some key areas you may be neglecting. Besides, you can’t pass level two without mastering the following:

  • Perfect Your Hairstyle– You can create all sorts of confusion determining what hairstyle fits you best. Before falling in love with a style, examine your face shape, hair color and hair type first. The sad truth is not all men will look good with a side part hairstyle or growing out his hair. The good news is there is a style that WILL suit you perfectly. Your best course of action is to go to a reputable hairstylist and get an in-depth consultation. It may take a few tries to find the perfect hairstyle for you but it’s worth it. A great hairstyle coupled with an awesome outfit will make you irresistible!
  • Have Pearly Whites–Take care of your teeth! You may never be called out for having yellow, dirty teeth from others but you can be sure they’re thinking it. On the bright side, having sparkly whites gets you as many compliments as a great pair of shoes would. Brushing should be a daily ritual you all should do (I hope). Don’t neglect to floss every day as well to get rid of remnant food particles sitting between your teeth and gum line.
  • Have Great Skin– Do yourself a favor and go to the nearest drug store and buy a high quality facial cleanser and daily moisturizer. Having unclean, dry skin makes you look tired and older than you really are. Imagine speaking to a room full a people with bad skin. You want people to hear your message not think about how old and tired you look.

If, you’ve come this far, I bet you look much more stylish and presentable from where you first started. Your physical appearance is looking stellar but now it’s time to walk the walk.

Skill Building

What do you consider to be good at? Is this something coming from you or are others bringing this up?

The truth is we all are good at something and we all can be good at many things. To master level two, you have to be well rounded and have skills that are wide ranging and useful.

I’m not here to tell you what to get good at. What I will do, is provide some universal principles to apply to the anything in life to get better at it.

Are you ready?

  • Get Out of Your Comfort Zone – The key is to learn to love challenges and enjoy facing hardships that come your way. The journey really is the best part, regardless of the skill. Set goals for yourself and do the best you can to achieve them in the time you lend for yourself.
  • Read and Read Some More – I’m an avid reader and try to at an absolute minimum to read a book a month but always aim for two. Books that help you improve are best but there is nothing wrong with reading fiction every now and then. It lets your imagination run wild.
  • Improve Your Body – If your goal is to be highly skilled in style and increase your confidence, you have to look the part. Exercise is the key to making that happen. Look to exercise consistently and eat a healthy, well balanced diet.
  • Network – Lastly, learn to like talking to people. Build a network of friends and acquaintances of people you enjoy spending time with and add some extra quality to your life.

WOW! Take a look at what you just accomplished. You now have a great foundational wardrobe, have better hair and skin while building some great skills in the process.

You have officially passed level 2 and made it to a territory few men have ventured.

While soaking in glory, take some time and really cherish what you accomplished. Even better, pass this article off to a friend in need of taking their style to the next level.

Stay tuned for the final 3 levels in this game of style. Any idea what they are?