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How A Men’s Dress Shirt Should Fit


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How should a dress shirt fit?

Seems like a simple question – yet look around you.

The vast majority of men are wearing dress shirts that are one to two sizes too large.


Why does this matter?

Simply put – an ill-fitted dress shirt:

  • Is uncomfortable
  • Makes you look less than professional

Either of these should be enough to motivate you to either have your current dress shirts adjusted to fit by a local tailor or consider buying custom dress shirts.

Although both options cost a little coin – the end result is a dress shirt that wears and feels great.



The details in a well fitted men’s dress shirt.

Dress Shirt Collar Fit

Just Right:The perfect collar fit touches the skin all the way around the neck, but does not press against it. You should be able to slip a finger in between your neck and the shirt at any point without struggling or forcing.

Too Tight: The collar is close enough to actually press against the skin underneath it. There’s a discernible sensation of constriction. It would be impossible to put a finger between the neck and collar without stretching, tugging, or forcing.

Too Loose: The collar does not touch the neck, but rather rests off the body. You could slip a finger in next to the neck without moving the cloth at all.


Dress Shirt Shoulder Fit

Just Right: The vertical shoulder seam sits at the edge of the shoulder, where the plane of the shoulder meets the plane of the outer arm. The armscye (the hole where the sleeve joins the shirt body) is large enough that there’s no tugging or twisting on the shoulder seam.

Too Tight: The seam will be shifted up the shoulder toward the neck. Some of the sleeve rests on top of the shoulder. If the tightness is in the armscye, there may also be twisting that causes wrinkles or distortion along the seam.

Too Loose: The shoulder seam slumps off the shoulder, down onto the outside of the bicep. There may be billowing under the arm as well, if the armscye is too big.


Dress Shirt Torso Fit

Just Right: The buttons close comfortable and the underside of the placket (the strip where the buttons and buttonholes are located) rests lightly against the sternum (the central bone of your ribcage). The shirt tucks in with no billowing at the sides.

Too Tight: The buttons strain to close, causing radiating wrinkles around the buttonholes. Tightness may also cause pulling on the sleeves, distorting the armscye and shoulder seams.

Too Loose: Excess fabric hangs slack around the stomach or chest, causing visible billowing. The shirt placket moves about and does not rest against the sternum. Tucking the shirt in causes billowing, ballooning, or “muffin-topping” near the trouser waist.


Dress Shirt Sleeve Fit

Just Right: The sleeve is slightly wider at the upper arm than the cuff, with a smooth, even taper. There should be some looseness when the arm hangs straight (so that the elbow isn’t constricted when the arm bends). Looseness should be evenly distributed, not bunched up at the shoulder or cuff.

Too Tight: The fit is snug when the arm hangs straight, causing pinching when the elbow or shoulder moves. Tautness may cause radiating wrinkles at the shoulder seam or elbow.

Too Loose: There is so much slack that gravity pulls it downward and creates hanging folds of cloth, especially around the cuff. Loose sleeve fabric can also flap and sway around the elbow and bicep.


Dress Shirt Sleeve Cuff

Just Right: The cuff is close to the body but allows a bit of space between the cuff and the skin. It should be possible to put the shirt on or take it off without unbuttoning the cuffs. Enough room for a pair of fingers (or for a normal-sized dress watch) is a good amount of slack.

Too Tight: It is impossible to pull the shirt off without unbuttoning the cuffs (or popping a button). The cuff presses against the skin all the way around the wrist. Wrist watches can only be worn below the hem of the cuff, and the cuff bunches up if it meets them rather than sliding over the watch.

Too Loose: The cuff is wide enough that it can slide loosely over a wristwatch and still have room for several fingers to be inserted between the cloth and skin. Folds or wrinkles form in the fabric of the cuff when the arms are rested against a surface like a tabletop.


Dress Shirt Sleeve Length

Just Right: The sleeve comes all the way down to the large wrist bone at the base of the pinky/ring fingers. If a jacket is worn, about a half-inch of shirt cuff should show beyond the end of the jacket sleeve. The cuff should at least touch (and in some postures cover) the wristwatch, if one is worn.

Too Short: The cuff leaves the wrist bones exposed, or is hidden completely beneath jacket sleeves.

Too Long: The cuff falls all the way to the point where the hand begins to widen outward from the wrist. This can cause bunching if the sleeves are so long that slack piles up behind the point where the cuff stops. If a wristwatch is worn, it is completely covered by the sleeve at all times.


Dress Shirt Bottom Hem Length

Just Right: When untucked, the hem falls far enough to cover the belt. It should be long enough at all points (including the sides, if the hems are scalloped) to tuck at least an inch or so into comfortably-worn trousers.

Too Short: The untucked shirt does not completely cover the belt or waist of the trousers. When tucked in, points of the hem remain exposed, or have so little cloth tucked in that they are likely to pop out when the body moves and bends.

Too Long: The shirttails fall all the way to cover the crotch in front or bottom in back. When tucked in, excess fabric has to be shoved down between the legs to hide bunching up.




Step 1: Figure Your Size

If you already know your dress shirt size, you can skip this step. If not, most dress shirts are sized with a neck/sleeve pair of numbers, which you can calculate this way:

  • Measure the circumference of your neck. Take the measurement low on the neck, where the collar of a shirt sits, and add 1/4″ to the measurement for breathing room.
  • Round your neck measurement up to the nearest half-inch. Off-the-rack shirts won’t be sized any more precisely than that.
    Record your collar size: __________
  • Measure the sleeve length with your arm held lightly at your side. Start the tape measure at nape of the neck and measure all the way down the top/outside of the arm to the end of the wrist.
  • Round your sleeve measurement to the nearest inch.
    Record your sleeve size: __________

The two numbers you have recorded will be your ready-to-wear shirt size. Most are listed with the neck size first, and many give a short range of sleeve lengths, so a typical tag might read something like “15 1/2 32-33,” for a neck size of fifteen and a half inches and a sleeve length of around thirty-two or thirty-three inches.

Men buying custom shirts may want to use a more detailed measurement guide that takes waist, chest, and additional measurements into account, such as the one at A Tailored Suit.

Step 2: Identify the Shirt You Want

  • Select a fabric:
    Oxford — a simple, sturdy weave with light bumps in its surface
    Pinpoint or royal oxford — a smoother, lighter oxford (more expensive)
    Poplin — a smooth surface with a light, loose weave
    Herringbone — a textured weave with distinct “V” shapes
    Broadcloth — a smooth, tight, high-quality weave (often expensive)
    Seersucker — light, bumpy, summer-weight cloth (casual)

There are many more dress shirt fabrics available, but these are the most common. Feel free to explore other options — these are a good starting place.

  • Select a collar style
    Button-down — sturdy but casual; not appropriate for business formality
    Point — the basic turndown shirt collar
    Spread — a wider-spread point collar, with the points more than 90 degrees apart
    Club — an uncommon style of rounded collar, rather than pointed
    Mandarin — a stiff collar that does not turn down
    Pin — a point collar held closed by a separate metal pin; only worn with ties
    Tab — a point collar held closed with tabs under the collar; only worn with ties.
  • Select a cuff style
    Single barrel — the most typical style, with a plain, buttoning cuff
    Double French — A doubled-over style sealed with cufflinks rather than a button
    Double barrel — An uncommon doubled-over style with built-in buttons
    Single French — Single cuff sealed with cufflinks; rare outside of formal (tuxedo) shirts
  • Select a color/pattern
    o Plain white — highest standard of business formality
    o White with light stripes/check — typical business formality
    o Light-colored solids — relaxed business wear
    o Bright solids or vivid patterns — casual/social wear only
  • Select a monogram if desired/offered

The combination of fabric, collar, cuff, and color/pattern should narrow your shirt choices down nicely. You’re much better-prepared for shopping if you can tell salespeople that you want “a blue-and-white striped poplin shirt with a button-down collar and normal barrel cuffs” than if you just say “I need a dress shirt.”

Step 3: Pick Your Source

  • Identify the kind of tailoring and construction you want:
    Bespoke (completely custom made — most expensive option)
    Made-to-measure (a pre-made pattern sized specifically to you)
    Ready-to-wear (pre-sized off the rack; some stores do in-house adjustments)
  • Select a type of store:
    Department stores (Sears, Macy’s, etc. — low prices, but limited selection/quality)
    Menswear chains (Men’s Wearhouse, Jos. A. Banks, etc. — wider selection and better in-house service/fitting)
    Independent boutiques (unique selections; tend to have better service and quality)
    Bespoke tailors (custom design and construction)
    Online (you send your measurements and payment; they ship you a shirt — can require several back-and-forth shipments to get fit right)

Step 4: Go Shopping

  • Head to your target store or stores (see step 3)
  • Identify the shirts that fit your selected description (see step 2)
  • Within that selection, find the shirt that fit your measurements (step 1)

With the information in this checklist, you should be able your selection down to just a few shirts. Find the one that suits you best at the price you like — or move on, if you need to, and use the same information to shop elsewhere, until you find a purchase you like.



_____Step 1: Figure Your Size

If you already know your shoe size, you’re done here — skip to the next step. If not, you can either go to a shoe store with trained service that can measure for you, or you can follow these step-by-step instructions to measuring at home:

_____Tape a blank sheet of paper (regular printer size is fine) to the floor

_____Put on the type of sock you’ll usually wear with the shoes you plan to buy (so that you’re taking the sock width into the measurement)

_____Place your foot on the paper (at an angle if necessary) and bend slightly forward, so that your knee is further forward than the shin below it.

____Trace the outline of your foot. The drawing tip of your pen or pencil should be snug up against the sock, not pushed out from it.

_____Now use a ruler to draw straight lines that just touch the outermost points on each side: front, back, right side, and left side. You don’t need to extend the lines until they cross, but if you did they’d make a long, narrow trapezoid.

_____Take your measurements, rounded to the nearest 1/16″:
o Length (from the front line to the back line): __________
o Width (from the right line to the left line): __________

_____Repeat all the above steps for your other foot, and use the larger measurements. Most people have one foot slightly larger than the other, and you want the shoes you buy to fit your largest foot.

Use the following charts to convert inches to U.S. shoe sizes. The first chart converts the length in inches to a numerical size, while the second uses the shoe size and the width in inches to assign a shoe width, expressed as a number. The combination — 9D, 14E, etc. — is your full shoe size.

Length in Inches to U.S. Shoe Size Conversion

Length in Inches U.S. Shoe Size
9.31 6
9.5 6.5
9.69 7
9.81 7.5
10 8
10.19 8.5
10.31 9
10.5 9.5
10.69 10
10.81 10.5
11 11
11.19 11.5
11.31 12
11.5 12.5
11.69 13
11.81 13.5
12 14
12.19 14.5
12.61 15

Width in Inches to Shoe Width Conversion, by U.S. Shoe Size

U.S. Shoe Size C (Narrow) D (Standard) E (Wide)
6 3.3″ 3.5″ 3.7″
6.5 3.3″ 3.6″ 3.8″
7 3.4″ 3.6″ 3.8″
7.5 3.4″ 3.7″ 3.9″
8 3.5″ 3.8″ 3.9″
8.5 3.6″ 3.8″ 4.0″
9 3.6″ 3.9″ 4.1″
9.5 3.7″ 3.9″ 4.1″
10 3.8″ 4.0″ 4.2″
10.5 3.8″ 4.1″ 4.3″
11 3.9″ 4.1″ 4.3″
11.5 3.9″ 4.2″ 4.4″
12 4.0″ 4.3″ 4.4″
12.5 4.1″ 4.3″ 4.5″
13 4.1″ 4.4″ 4.6″
13.5 4.2″ 4.4″ 4.8″
14 4.2″ 4.5″ 4.9″
14.5 4.3″ 4.6″ 4.9″
15 4.3″ 4.6″ 5.0″

_____Step 2: Identify the Shoes You Want

_____Select a material
o Leather w/leather sole — dress shoe standard
o Leather w/rubber sole — traditional “work shoe”
o Exotic leather (usually only for social wear, not business)
o Canvas/cloth uppers (skate shoes, espadrilles, etc.)
o Rubber/synthetic uppers (athletic shoes, etc.)

_____Select a style
o Oxford/balmoral — highest business formality dress shoe
o Blucher/derby — slightly more casual business style
o Brogue — casual, decorated leather shoe
Wingtip — heavily decorated casual style
o Saddle shoe — casual style; usually two-tone
Dress boot — high-ankled leather shoe
o Loafer/driving shoe/moccasin — slip-on leather shoe
o Boater — leather upper with crepe rubber sole slip-on
o Sneaker — soft, rubber-soled casual shoe
o Athletic shoe — multi-piece casual shoe, often with breathable mesh
o Work boot — thick rubber sole with high leather or synthetic uppers
o Sandal — open-toed casual summer style

_____Select a color
o Black — highest business formality standard
o Dark brown — acceptable for some business wear
o Oxblood/burgundy — acceptable for some business wear
o Light brown — casual/social color for leather
o Two-tone — decorative, casual style
o White — flashy dress style (white bucks, etc.)
o Dark blues, greens, purples, etc. — sometimes seen on suede shoes
o Bright colors — usually reserved for athletic shoes, sneakers, etc.

The combination of material, style, and color gives you a very specific shopping target. Once you can narrow a store’s selection down to something like “a dark brown leather brogue,” there should only be a manageable amount of shoes left to choose from.

_____Step 3: Pick Your Source

_____Select one or more of the following sources for footwear:
o Department stores — cheap, but limited selection/quality
o Chain shoe stores (DSW, etc) — cheap, with a wide selection, but mixed quality
o Boutique shoe stores — limited selection and high prices, but often select only high-quality stock
o Bespoke cobblers — custom-made shoes; very expensive but generally the sturdiest and most comfortable shoes available
o Online shopping — easy and wide selection, but may take several exchanges for sizing

_____Step 4: Go Shopping

_____Go to your target store or source for footwear (as chosen in Step 3)

_____Identify the shoes that match your chosen style (from Step 2)

_____Select the ones in your size (from Step 1)

These are your options! Hopefully, you should have narrowed the selection down to just a few pairs of shoes. If the store doesn’t have any that quite suit you, move on — with your checklist, it’s easy to browse multiple stores in a short period of time.

With shoes, be sure to try them on and walk around the store a bit even if you find a pair you like in exactly your size. Not all companies construct their sizes in exactly the same way.



Rules On Wearing Pocket Squares

So I’m going to talk about each of the four garments:

  1. Shirts
  2. Vests
  3. Jackets
  4. Overcoats
  1. Shirts

The dress shirt is probably the closest to the body so pretty much, I say never.

I don’t like the look. I’ve seen some guys try to pull it off but really a shirt breast pocket? I don’t even like making shirts with breast pockets. I usually recommend men not to have it. And even if you buy something off-the-rack, a lot of times, you can remove the pocket as well.

There are many reasons to have a pocket.

I’ve got a good friend in sales and he’s always moving and he keeps pens in it. In fact, the shirts I make for him have special pockets on the inside for holding his pens. He doesn’t really use ones that leak ink, so I don’t think he’s ever actually lost a shirt, to those of you that object to that.

But if you use it, go for it but don’t stuff it with a pocket square.

  1. Vests

My answer is you can wear a pocket square with a vest sometimes.

No – If you’re wearing the vest under a jacket.

Yes – If you’re wearing the vest by itself.

I’ve seen the latter being done by a lot of men.

I’ve got a good friend who’s a photographer. He’s at weddings all the time so he wants to have his arms free because he’s moving and he uses the pockets to actually hold pieces of gear but still he wants to look good.

I think he wears a bow tie with the pocket square and it looks good. It shows that he went the extra mile but at the same time, he’s at work so he follows the function path.

I always believe function first, style second. So in that case, it looks great.

  1. Jackets 

I think a jacket should always have a pocket square.

I know it takes a while for guys to get used to it. I have a client over in lagos named Kunle. He talked about how he just left the other day and forgot his pocket square.

He actually stopped at a store to buy one because he felt incomplete without it. When you can get to that feeling, it’s a great place because people notice these pocket squares.

Start off small.

Start off with white.

The guy knew how to dress and he looked good. He always had that little square fold there.

  1. Overcoats(Trench coats and any type of jacket)

Here is where function happens. An overcoat is there to protect you when it’s cold outside. No need for a pocket square there.

Most likely you’re wearing a jacket underneath and that’s where you would have the pocket square.

You may say, “Well, why does it have a breast pocket?” 

That’s where you could possibly put your gloves or to put sunglasses or something in that pocket. It’s not really so much for adornment. That one is more for function.

And there you have it.

I talked about the four points:

  1. Dress shirts – Never.
  2. Vests – Sometimes especially if you’re wearing it by itself.
  3. Jackets – Always.
  4. Overcoats – Rarely.




  1. Navy Blue Suit

The number 1 and 2 rankings of suit color in this list may be interchangeable especially in North America.

However, navy blue edges out charcoal grey by a little as throughout the United States, navy blue is considered the de facto color.

All stores specializing in men’s suits will carry a navy-colored one.

Navy suits are ideal for the man who wants to fit in. He wants to be recognized for the effort that he puts in and not necessarily what he puts on.

Another advantage to a navy suit is that if a gentleman wants to get it customized he can include a few fashion forward details because the color is so simple and straightforward.


  1. Charcoal Grey Suit

A charcoal grey suit is just about as versatile as navy.

The one advantage that it has over the former is that it is more idea for the younger man as it can add a little more age to him.

Navy suits can make a young man look even younger while charcoal grey does not have that same effect.

Charcoal grey is extremely easy to match. As that charcoal is firmly on the grayscale (absent of color – a neutral) it goes well with a wide range of colors allowing a man to be more adventurous with the shirts and ties that he pairs this suit with.

When it comes to formality – this is adequate for work, church, weddings, funerals, or meeting the president.


  1. Cambridge/ Medium Grey

There are many shades of grey which means that there is a marked difference between charcoal grey and medium grey.

A medium grey suit will be a little lighter compared to charcoal.

In terms of versatility it is still about equal to Cambridge grey.

However it is not as formal as charcoal grey and navy blue although very few people and places will be able to tell the difference.

Having the three suits mentioned above will already make for an extremely versatile wardrobe, especially if each suit had slight differences in the details that go into them.


  1. Light Grey Men’s Suit

A light grey suit is distinctively lighter compared to its other grey brethren.

This suit works well for spring, summer and fall dressing.

The light grey suit is more casual. It is ideal to invest in one once a man has all of the “must-haves” in his wardrobe.

This shade is a great way to break up the monotony of wearing the more usual shades.

The lighter the shade the easier it is to introduce pattern-such as checks or herringbone-into the suit as the patterns are easily more visible.


  1. Black Men’s Suit

The black suit only gets 5th place because compared to the ones previously mentioned it is not as versatile.

Black does not work for every skin type. A black suit works well for a man with a darker complexion and dark hair.

A black suit does not look flattering on a man with lighter complexion and light hair- such as a redhead as it can easily wash him out.

Black suits are limited in their versatility due to the stark contrast with anything else you are wearing.

A black suit is useful for the most formal of occasions such as a black tie event.

If you’re going to an event which requires a tuxedo or a black-tie dress code make sure that your suit is truly black. A black suit is also appropriate for funerals.


  1. Dark Brown Men’s Suit

A dark brown suit can work if a man has dark hair and a darker complexion.

It can work for some blonds, redheads and for men with ruddier complexions.

A dark brown suit can be effective in adding a little bit of color.

However those who choose to wear it should exert caution as it is clearly not a formal suit.

Never wear a dark brown suit to a formal event or to a place where business dressing is taken very seriously (world cities such as New York and London).


  1. Tan/ Khaki

A tan suit falls under the category of a brown suit as they fall within the same color family.

However – for this article I separate them as for summer wear they are more at home in warmer weather and could easily surplant the brown suit in this list due to their versatility assuming you have the weather and complexion to pull it off.

Like the light gray suit a khaki one can spice up the wardrobe especially for the man who constantly wears suits to work.

They are are a solid choice for low contrast men as the lack of color won’t overpower neutral features and allow you to wear pastels to more effect.


  1. True Blue Men’s Suits

Compared to navy, a true blue suit can be harder to find.

The jacket to the left is an example – please note it is being worn as a sport jacket hence the non-matching trousers.

Public personalities & politicians such as Prince William, Prince Harry and Vladimir Putin have popularized the hue and it is actually a good color to wear.

A true blue suit is more popular in Europe and parts of Asia. However it doesn’t score very high for North American based gentlemen because it is simply difficult to find and less formal than Navy.

A man may have to consider getting a custom suit made if he wants a true blue one. A great option if you own close to a dozen suits and want something for weekend or events a formal color isn’t required.


  1. White Men’s Suits

 The final suit color is white.

Unless you’re a major personality such as Tom Wolfe– who made the white suit his signature look – the white suit will more often appear as an oddity.

Wearing a white suit draws attention to oneself. Therefore it can be ideal for events like white parties, or when you have to make a major presentation and really command everyone’s attention.

However a white suit is not really a necessity and men should not prioritize having it as part of their collection.



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