How a Shirt Should Fit

Why is this subject so important? Because your clothes are working for you or against you. There is no middle ground. People will react favourably to you if you come across as:

Enthusiastic, competent and knowledgeable. Clothes that fit signal that you are competent. The opposite is also true. You are giving yourself an advantage to let your clothes indicate your intelligence for you rather than having to prove it in dialogue.

Getting a shirt to fit just right is difficult because it is a BALANCE. Not too loose and not too tight.


Shoulders are the most important part of the shirt. This piece is very difficult to alter and is the foundation of the shirt. Ideally the shoulder yoke of the shirt should fall point to point at the intersection of the two planes that are the shoulder and the arm.

Ask your clothier for two awesome shirt features. 

  1. A Split Yoke. In the 1800s a Split Yoke was the mark of a quality shirt and it still holds today. A split Yoke means the shoulder yoke of the shirt is made in two separate pieces and this will allow more flexibility and movement in the top part of the shirt.
  2. Shoulder Pleats. This will allow greater ranger of motion in the upper chest and back area.
  3. For Bigger Guys – Get a Box Pleat instead of Shoulder Pleats. Allows for maximum range of motion.

The combination of these features allows for a trim look without sacrificing mobility. As in we don’t need to add extra fabric around the chest to help you move.


When wearing your shirt you should be able to hug yourself without splitting the back. You should be able to lift your arms without feeling extremely limited.


The waist should look fitted while still giving you ample room for comfort or a thanksgiving meal.

Ask your clothier to pre-dart your shirt. This will create great shape for those with an S Curve spine. Also means the darts can be let out. If you gain weight, the darts can be let out and you can still get use out of your shirt.

TANGENT: Wise people often save money by spending more at the outset on quality and knowledge, the ability to pre-dart your shirts is one of those examples. 


You want the seat to be able to support wearing tucked or untucked. Ideally it falls so that the placket covers the inner placket without much excess.


The ideal length of your dress shirt is 2/3 down the crotch. This makes the shirt versatile as it can be worn casually or formally. You should be able to tuck in easily without the shirt coming out or without excess fabric. You should also be able to wear untucked casually.

Pro Tip: Ask your clothier to make you shirt at a length that you can wear untucked with a blazer. This gives you tons of flexibility with your wardrobe and gives you so many more options and outfits

Sleeve length

The actual length of the sleeve should be seemingly too long. The actual point of fall depends on height and personal preference. With the cuff unbuttoned and the arm relaxed, the shirt should fall halfway down the hand. The key is having the proper cuff width will make this work extremely well. This ensures we have some slack in the sleeve and when we shake a hand our cuff doesn’t shoot up our jacket.


Generally you want to be able to fit two fingers under the collar comfortably but not much more than that.

Aim is to look good with a tie yet be able to wear that tie all day long comfortably. Even if you are buying a casual shirt you should still ensure you get a proper neck measurement. This way when you need a formal shirt in the future you can simply order the shirt to the exact size specifications as your casual open collar shirt and be confident the fit will work.


I like my cuffs to fit over my watch but not so wide that they fall too far down my hand. I buy nice shirts so I want those cuffs to show when I am wearing a suit or a blazer.

When visiting your clothier wear your biggest watch or your favourite watch to wear when dressing. Two different watch looks with your cuff are the full watch showing or the partial watch showing. I am partial to the partial. However, if I want to make the watch pop I will fasten the inner button. For this reason, I recommend asking your clothier to give you a two button horizontal convertible cuff. This gives you 2 sizing options and allows you to wear cuff links with a button cuff shirt. You know that is awesome!


The pipes gotta be accentuated without making it look like that is your aim. When you get to the top position of the hammer curl you shouldn’t be bursting out of the shirt. The shirt itself shouldn’t be billowing either.

When wearing your dress shirts I highly recommend wearing an undershirt.

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