Welcome to Module 5: The Style Scale: How to Create Amazing Looks and Ensure You’re Never Under (or Over) Dressed

You’re almost done!

In the previous Modules:

  • We learned a few essential points on fit, like “the clues are in the construction” and “the cut in half” rule, to quickly master fit.
  • We stocked our wardrobe with classic essentials in neutral colors, making mix and matching completely effortless.
  • We learned to create a few Go-To outfits for those times when we don’t want to think about our outfits.

Today, we’re going to take everything you learned in the previous lesson and put it together, creating a bulletproof system for looking your best. A “system” to apply to your wardrobe to take advantage of how versatile it really is.

You’ll feel confident enough to know your outfits are not look amazing, but are appropriate for whatever situation comes at you.


It’s important you have a few things before you start this lesson. If you can’t check off all these points right now, pause, go back into the previous modules and work on them. When you’re ready, come back. I’m not going anywhere!

So before you continue with Module 5, make sure you can say yes to all of the following:

  1. You’ve Identified Your “Style Needs Type”
  2. You can comfortably identify someone, including yourself, with good or bad fit based on the “clues in the construction” and “Cut in Half” techniques
  3. You’ve picked up and stocked a closet of essential, Level 1 pieces. At least 75% of your “Style Needs Type” Checklist
  4. You have at least 1 “Go-To” outfit and can comfortably put together at least 2 more

You’ll see soon why it’s very important to be able to confidently say “YES!” to all of these points.

You don’t have to be a masters of any of the lessons in the Modules, of course. As long as you have a working knowledge of the lessons.

It’s important that you’re applying these techniques when you’re out shopping or dressing, rather than sitting at home going over the lessons until you are mentally perfecting it. As I mentioned in the beginning, you can’t get better at dressing if you’re not going out and getting dressed!

Take as much time as you need to hit these points, especially if you haven’t had the time or money to check off 75% of your Wardrobe Checklist.

Once you’ve checked off all this stuff, move onto the next steps.


Step 1: Create 3 Main Go-To Outfits For 3 Common Situations

“I don’t know what to wear. I don’t know what’s appropriate.”

Have you ever said this to yourself?

Outside of stocking a versatile wardrobe, figuring out if an outfit is appropriate is a difficult challenge for my clients with a casual style.

What do you wear to a casual networking event that says “business”? How do you dress up for a weekend night date without looking like you’re going to work?


Today I’m going to introduce you to what I call “The Style Scale”

The Style Scale allows you to sort a few “Go-To” outfits by how casual or formal they are. Then, using some of the techniques we learned, gives you a guided way of tweaking outfits as you need.

For The Style Scale, we’re going to use three principles you’ve already learned:

  1. The “Go-To” Outfit principle
  2. “Swap One” technique
  3. “Style Needs Type”

Think of your “Go-To” outfits on the scale as “templates” you can tweak depending on your situation.

Say you have a business casual meeting at work, you can take your “Go-To” work outfit and swap out one or two things to make it more formal.

This is another example of front loading the work. Your Main Go-To outfits give you peace of mind, giving you a starting point to create an endless amount of outfits.

Screen Shot 2016-03-27 at 3.04.31 PM
I call this look “I’m The Boss”

If you’ve been a reader of my articles for a while, you’ll notice that at the end of almost every post I put together 3 looks based on 3 scenarios.

I imagine, or even use real scenarios my readers and clients often find themselves in, creating outfits they can use. This gives outfits context and helps understand how to dress for occasions, whether that’s a day-to-day office job, date at a speakeasy bar or a casual networking event.

Today, you’re going to do the same exercise. You’re going to create 3 “Go-To” outfits that are appropriate for 3 common situations. An outfit for the weekend, work and events/meetings.

The 3 “Go-To” Outfits Are:

1. The Weekend (Casual)
This is your “Go-To” outfit on the weekends. It’s going to be your most casual Go-To outfit. Now, this doesn’t mean your pajamas and t-shirt. Get out of the house! What would you want to wear if you have a free Saturday and decide to have a long lunch somewhere with your girlfriend or wife?

2. The Office (The Middle)
Your Go-To work outfit is what you’ll often find yourself in. It will most likely be less casual than your weekend outfit, thus, placing it right in the middle on the scale.

3. The Business Meeting / Event (Formal)
Your most formal outfit on your scale will be the one you’d wear at a business meeting or event. For the “Smart Casual” and “Business Casual”, that might mean a full suit (with a polo or button up shirt, sans tie). For the Effortlessly Casual, that might mean your navy blazer.

Action Step: Create your 3 “Go-To” Outfits and place them on The Style Scale. You’ll need this for later in the lesson.

Need an example? Recall the image in the beginning. It’s an example of 3 Go-To outfits on the Style Scale using the “Smart Casual” wardrobe:


On the far left, a Weekend Go-To. In the middle, a Work Go-To, and on the far right a Business Go-To.

Remember, this is YOUR scale. There isn’t really a right or wrong answer here.

You can stick to Level 1 pieces, or mix different Levels together. It’s up to you! The Go-To Outfits and the scale are supposed to suit your needs. It can and should be totally different than mine, or another students.


Step 2: Learn to Identify Appropriateness

So, how do we adjust Go-To outfits to make them more casual or more formal?

By using The Swap One technique!

Say you have a networking event for entrepreneurs to go to. A little research tells you it’s a casual business event, so wearing your charcoal grey suit would be a bit overkill.

At the same time, you don’t want to show up in a leather jacket and sneakers, that would be a little too casual.

You want something in-between your Go-To work outfit and your Go-To event outfit.


So, you start with your Go-To work outfit. Using The Swap Technique, replace the leather jacket with a Navy Sports coat, and the shoes with a Level 2 Oxford to match the color palette.

You used your Go-To work outfit as a jumping off point, creating a new outfit that sits perfectly in-between your casual workplace and your most formal option.

This is not just for “dressing up” a Go-To outfit. You can take a Go-To outfit down as well. If you wanted to dress down the Go-To work outfit above, you could swap out the oxford for a t-shirt and chinos for jeans.

This might seem obvious, but I highly recommend you organize your Go-To outfits and think about outfits on this Style Scale. Having 3 Go-To outfits to guide you in putting together outfits will save you stress and time later on.

Now, before you start, you’ll need to learn a quick way to decide when something is more formal or more casual.

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In general, the more details a piece of clothing has, the more casual it is. (To put it a simpler way, the more minimal and simple a piece is, the more formal it is).

Look at the image above. The details, washed denim treatment, pearl buttons, breast pockets make the chambray shirt on the left the most casual. As you have less and less details, and the colors get more solid, the chambray shirt gets more formal as seen on the far right.

Some quick rules of thumb when deciding how casual or formal a piece is:

(LEFT) More details such as the color and two chest pocket make this shirt more casual compared to a plain white button-up shirt (RIGHT)

Details such as more pockets, zippers, stitching and design details make a piece of clothing more casual.


Colors outside neutrals such as red, blue, purple, or patterns make a piece of clothing more casual.

Casual fabrics, like cotton, will generally be used for more casual pieces of clothing like chinos. While wool suitings are used for more formal pieces.




Exercise: Take 5 minutes. Look at these 3 sets of clothes and rank each piece in each set. Sort them from “Casual” (1) to “Most Formal”(3). Compare your answer to mine below.






Pants: While the dress pants are the most obvious choice for most formal, the jeans and chinos are trickier. If we remember the “more details, more casual” rule, we know that the pair of jeans is more casual than the chinos. The denim has extra pockets such as the coin pocket, along with metal rivets and topstitching.


Button Up Shirts: “The More Colorful, The More Casual” rule tells us that the red shirt is more casual than the grey, and the blue plaid shirt is more casual than the red.

test3Sports Coats: This set is subtle, but in the right order. The patch pockets on the 3rd sports coat make it casual. But despite the middle sports coat’s traditional cut, the wild plaid make it more casual in comparison to sports coat #3. It’s not just the extra chest patch pocket that puts sports coat #1 as the most casual, but the fabric. The linen comes off extremely less refined as the other two coats, placing it in the #1 spot for most casual.

How’d you do?

Step 3: Use the Steps Above to Create 2 New Outfits

Let’s put these concepts to good use and create 2 new outfits.

I’m going to give you two scenarios and your action step is to create 2 new outfits.


1. The Casual Weekend Date
You and your date are going out this weekend. A nice bar and dinner, nothing dressy, but you still want to look nice. A weekend casual look would be too casual, so something in-between your Go-To Weekend outfit and Go-To work outfit would be perfect.

2. The Casual Networking Event
You replied yes to a meet-up on Facebook for other entrepreneurs. Clicking around the invite, you see photos of past events. The dress code is business casual, leaning towards casual. Going in a full suit would be overkill, but you want people to take notice of you. Create an outfit on the scale between your Go-To Work outfit and Go-To Business/Events outfit.

I know that this Module can be a bit of a challenge. As you continue to build your wardrobe, you’ll find the process of putting together outfits that go from casual to formal will get easier. Don’t be discouraged. You can get far focusing on your wardrobe and a few Go-To outfits.

Keep The Style Scale in your backpocket. When a situation or event comes up, pull it out and use these these techniques to create the perfect outfit without the headache.



  • 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.


  1. Create 3 Go-To Outfits for common situations: The Weekend, Work and Business Meetings/Events
  2. Take the quiz to practice identifying how casual or formal a piece of clothing is
  3. Use all the lessons in this Module to create 2 new outfits based on the scenarios given: The Casual Weekend Date and The Casual Networking Event.