A Man’s Guide To Dressing Better (Part 2) - Chris Boudy
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A Man’s Guide To Dressing Better (Part 2)

Dec 26 2015

A Man’s Guide To Dressing Better (Part 2)

In Part 1 of our A Man’s Guide To Dressing Better, we discussed the why we would even want to do this. For me, I wanted to dress appropriately for my age. For you, it could be anything. The point is that if you are reading this then you are taking dressing better seriously. So let’s get started with what you actually have to do.

Be Committed

The very first and most important piece of advice that I can give you in dressing better is: be committed. This will be a marathon and you must pace yourself for this race. Tell people what you are about to do. I told my family and friends that I would start taking better care of my appearance so they could hold me accountable and give me encouragement.

Take An Inventory

Go in your closet and take an inventory of what you currently have. You can write this down in a notebook, type up a document on your computer, or use an app to keep track of what you have. We’ll use this later on. Your breakdown should look somewhat like this:


  • Dress Shirts
  • Casual Shirts (Long or Short Sleeve)
  • Polo Style Shirts
  • T-Shirts


  • Dress Pants
  • Casual Pants
  • Denim Jeans
  • Chinos


  • Dress Shoes
  • Tennis Shoes
  • Sandals/Flip Flips
  • Boots
  • Casual Shoes


  • Winter Jackets
  • Sports Coat
  • Blazers
  • Pea Coat
  • Casual Jacket


  • 2 piece suit
  • 3 piece suit


  • Belts
  • Ties
  • Tie clips
  • Sun glasses
  • Watches

Understand Your Fit

Most of the time I see men who dress poorly not because they don’t know what to wear but that what they have on does not fit them. To dress better, you need to know your fit., or what size you really wear.

Before I started on my quest, I wore medium (size 15) dress shirts, size 32 pants, and 34 to 36 waist belts. This was not my actual size! And as I looked back at old pictures of myself, I wondered why I looked so sloppy. If was because my clothes were ill fitting.

Finding Your Fit

Get some soft measuring tape and have someone help you find the following measurements. See this quick guide on how to take measurements if you’re unfamiliar with the process.

  1. Neck Circumference: Mens shirts are measured in two parts, the first is neck size.
  2. Arm Length: The second part of men’s shirt measurement is the sleeve or arm length
  3. Chest: This is the measurement around the fullest part of your chest. Good to know for jacket sizes.
  4. Waist: The circumference  around your waist for pants/jeans
  5. Inseam: Also used for the length of your pants. Measured from the top of your inner thigh to a little bit past your ankle.
  6. Shoe Size: You may already know this but it’s good to go to a shoe store and get a proper measurement.

Keep in mind that all clothes are not properly  sized.  Depending on the style and type of clothes you may need to go one size up or down. But finding your fit can provide you with a starting point.

I’ve created a Measurements Wallet Cutout that you can use to write down your sizes. I found it helpful to put in my wallet to carry around.

Cycle Out The Old For The New

The reason why we did an inventory of your clothes earlier in the process was to figure out what we can keep and what we need to let go. During my own process, I found out that 75% of my clothes either didn’t fit, was unwearable because of permanent stains, or was unrepairable.

It would have been unreasonable to get rid of 75% of my clothes. So I did the next best thing. I cycled out the old for the new. When I got a new dress shirt, I gave away an old dress shirt. When I got a new pair of dress shoes, I let the old ones with the holes go.

Determine Your Style Lane

What you wear and what you want your wardrobe to look like also depends on the type of job you have. An executive will need a different wardrobe than a creative professional. Your “lane” will be a style guide that you want to achieve. Below is a basic wardrobe that you can work toward.

Style Lane Guide

Style Lane Guide

I should also note that this is only a guide. I fit in between the creative professional/white collar lane but like to dress a level up. Personally I feel more comfortable in business attire than casual attire. Find what you feel comfortable with to create a style that fits you.

Create A Wishlist/Create A Budget

Now that you know what you need to get rid of, you know your fit, and have figured out what style you want to pull, it’s time to create a wish list and a budget.

You should create a wish list of the clothing items that you need. Separate them by categories:  shirts (dress/casual), pants (jeans, dress, casual), shoes (dress, tennis shoes, boat shoes, boots, casual), suits, sweaters, accessories (ties, belts, tie clips, socks).  I wear mostly dress shirts to work so on my wish I wrote down:

  • 5 solid dress shirts
  • 5 pattern shirts
  • 5 ties

Remember earlier I said that building your wardrobe is a marathon. Financially, I could not go out and purchase ten dress shirts and five ties at once. But when I saw something on sale or got a gift card to a clothing store I had a plan of what I needed.

You also need to create a budget to purchase the new clothes you need. I set aside $50 a month and with that money I started to either buy the items off my wish list or put that money aside to purchase more costly items on the list later.

In part 3 of the series, we’ll talk about where to get clothing ideas from and how to find good clothes on a budget.

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