Dress shirts are one of those wardrobe items, we all own plenty of them, but it is all too often that I see men with poorly fitting shirts around town, I admit initially it is a difficult process to find a 'perfectly' fitting dress shirt, but should we be compromising on a item of clothing that many of us wear every day?

Lets go through the basics elements of the 'perfect' fitting dress shirt.


The seam where the sleeve meets to the body of a well fitted dress shirt should hit close to the top of your shoulders. A common compromise of many brands is to intentionally cut their shirts large and as a result for most men the seam will slide down onto the arm. You really want to accentuate the contours of your broad shoulders and let the fabric drape over neatly.

This is one trouble area I frequently have with dress shirts because I tend to wear my dress shirts with ties often, if you wear open collar then the collar size is not so crucial. Traditionally the collar size is measured in inches from buttonhole to button when laid flat. You should be able to button the collar easily with room for two fingers to fit—any more and it's too loose, any less and it's too tight. 

The armhole of a dress shirt will determine how well the shirt will fit in regards to its chest, shoulder and armpit most 'off-the-rack' shirts will cut their armholes big to fit a wider range of body types. Your armhole should be contoured in a way that creates a tapered feel under your arm, but not restricting a full range of motion. Creases under the armpit is a sure indication that the shirt s too tight and will be extremely uncomfortable.

Your chest should always 'fill out' the shirt in a way where your body is accentuated under the fabric (if not its time to hit the chest press at the gym some more). A well fitted dress shirt will fit comfortably around the chest, armpits and across the shoulders to give you a full range of motion. The shirt should be snug and never too tight, the buttons should never pull.

A great fitted shirt often has back darts that allows the shirt to taper at the waist to the chest, following the contours of the body and creating a clean line between the shirt and pants when tucked in, with little excess fabric. I am noticing men wearing slightly more relaxed shirting, which is great to see also, after all comfort always comes first. 

As a rule of thumb, when buttoned the cuff should fall right at the base of your thumb, Just like your chest, your arms should fill out the sleeves of your shirt in a way that doesn't leave excess fabric. Excess fabric in the sleeves is never a good look.

A mens shirt hem should be long enough for you to comfortably wear the shirt either tucked or untucked. In you are unable to tell from observing proportions. a proven method of determining if the length of a dress shirt is right is by tucking it in and raising your arms above your head, see if the tail pops out, if it does then the shirt is too short. 



The key to a 'perfectly' fitting dress shirt is when you are able to tick as many of the above boxes as possible. consider the pressure points I have pointed out and find a shirt that suits your unique body and size and trust me when you tick all the above boxes you will not only look well put together but will also feel incredibly comfortable and confident.

I suggest next time you are at the stores, have a chat with your shirt fitter or tailor about how a dress shirt should fit your unique body. never be afraid to ask questions, they will be more than happy to share their knowledge. Education is much apart of the retail experience in todays world. Always keep learning. 


A few of my favourite Shirt Makers

Saibu No Akuma

Rhodes & Beckett


dress well, drink well, live well.