The Dude Society

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Beginner’s Guide To Dress Shirts & Cufflinks

So you need a dress shirt and are faced with a number of choices.  Don’t make the wrong decision.  Here are some basics about collars and cuffs on dress shirts, how to choose, and what to wear with them.

First, let’s talk style

We are talking here mainly about dress shirts that you would wear to an office job or with a suit.  The kind you buy from a place that has different neck sizes and sleeve lengths with various cuff and collar styles (I prefer Thomas Pink).  There are other slightly more casual dress shirts from some very top name designers that look fantastic (think Theory, Prada, and John Varvatos), but are less, shall we say, “classic” in style.  In any case, they will never be short sleeved.  As for fit, you have a choice of regular or slim.  If your figure is not slim, neither should your shirt.  Simple.

To start, have them measure  your neck, learn it, know it and do your best to make sure it doesn’t change.  There is nothing more uncomfortable than buttoning the top button of a shirt to put on a tie and realizing you can no longer turn your head or breathe comfortably.  Sizes are in inches and come in full and half sizes (e.g 15, 15 ½, 16, etc.)

You have a choice of collar styles to select from

  • Pointed Collar – these are what you see on most shirts, they are pointy, longer and have the points set fairly close together
  • Spread or Cutaway Collars – shorter with the points spread wide apart
  • Button Down Collar – these are standard pointed collars with buttons to button them to the shirt
  • Wing Collar – these are the tiny bent tips at the top of a collar that you normally see on a tuxedo shirt

Which collar style to choose?

Well, unless you are wearing a tuxedo we have already eliminated wing collar, the last from the list.  Button Down collars can also be eliminated unless you are only going to wear the shirt casually.  They were adapted from Polo player shirts who used them to keep the collars from flapping in their face as they rode horses.  Since you are unlikely riding a horse, much less playing polo, you should probably avoid these.  That said, having one to wear with jeans is an ok idea.  You will of course never wear the button down variety unbuttoned.  That would be like driving around with your car trunk open.

This leaves us with Spread and Pointed collars.  You can really choose either one, but here are some guidelines  If you have a very round, chubby face you want to avoid the spread collar as it accentuates said face.  You will end up looking like the Jack in the Box mascot.  The other thing to take into consideration is what type of tie and knot you choose.  A wider, for example Windsor, knot may look better with a spread collar.

Get your collar in check

Whichever of these two collars you choose, it is important that you always put in Collar Bones (sometimes called Collar Stays).  Lift up your collar and you will find a little pocket in each one.  Those are designed to hold Collar Bones.  They keep your collar down, and straight.

You will discard the flimsy plastic ones that came with your shirt, as they will not do the job.   You are not going to wear your shirt with the tissue paper still in it nor will you wear it with the flimsy collar bones.  You will buy ones made of sturdy plastic, brass, silver, etc.  You will also always remember to remove them before sending the shirts to the cleaners.  Otherwise you run the risk of a) losing them or b) having them left in the shirt during pressing which leaves ridiculous looking outlines of the collar bones on your collar.

Moving to the shirt sleeves

The length of dress sleeves should be such that they come just to your wrist and when wearing a suit jacket extend beyond the suit jacket sleeve, but no more than a half-inch.   Unlike neck sizes, shirt sleeves are measured in centimeters, why, I don’t know.  Usually you don’t have much of a choice here, there may be one or two shirt sleeve lengths for a given neck size.  As the neck size gets bigger the sleeve lengths get longer, presumably because you are a bigger man.  If you proportions are such that your width is larger than your height you will have a problem here and will need to get the sleeves tailored.

As for cuffs, you have two choices.  The first is the standard Barrel cuff.  This is what you see on most shirts.  It is just a band of fabric fastened with one button (single barrel) or two buttons (double barrel).

A second choice is the French cuff.  These are the style worn with cuff links.  It is a double piece of fabric folded over on itself and secured with cuff links.  While these may seem a bit stuffy or fussy, they are very much in style and do not need to be worn only with a suit jacket.

Some guidelines for choosing cufflinks

  1. Cufflinks should be simple and not overly ornate.  Made of Gold, Silver or Platinum only.  No plastic and no cheap metals.
  2. They can be plain metal, have an enamel design, or a semi-precious stone.  Save the diamond crusted ones for the tuxedo.
  3. Avoid being cute with them.  While you may like to make everyone aware of your manliness, stay away from ones shaped like naked ladies.  Likewise, dice, horse heads, golf clubs, sail boats, race cars, etc.  No novelty cuff links of any kind.
  4. For a more casual look you can choose to wear silk knots.  A color and pattern should be chosen that compliments the shirt you are wearing them with.  Thee go well with jeans.

Here are some examples of cufflink styles from my own collection. Silk knots are pictured on the right.

Example Cufflink Styles

When fastening cufflinks, you have two choices, the most common and standard way is the Kissing cuff.  This is where both ends of the cuff touch and you slide the cufflink through.  You will see the nice part of the cufflink on the outside of your wrist, and the back of the cufflink on the inside of the wrist.  The other choice is the Barrel cuff  and is where the ends overlap creating a barrel style cuff.  The cufflink goes through so the nice part of the cufflink is exposed and the back of the cufflink is hidden inside the cuff touching your wrist.  This is a far less common way to wear the link.

If you choose to wear cuff links, I highly recommend shopping for some nice vintage ones.  They are not much more expensive than nice new ones and you get to add a bit of history and uniqueness to your outfit.  One place I choose to purchase such links are from the Missing Link in NYC (the store is much better than the website).  They have 10’s of thousands of cufflinks in a range of prices and styles.  They have supplied many celebrities with cufflinks, and have been featured in many magazines.  You can visit them or call for assistance.

So there you have it, go buy some nice dress shirts, some collar bones, vintage cuff links, silk knots and add some snap to your style.

About the author

Rich is the resident food & drink expert. He's been cooking since age ten, and has probably eaten and drank at most every restaurant or bar in New York City.

All articles by Rich »

6 responses to “Beginner’s Guide To Dress Shirts & Cufflinks”

  1. Gaurav says:

    An inexpensive source of reasonable quality shirts is Charles Tyrwhitt and all their shirts come with brass collar stays, and the option of French or regular cuffs. They aren’t Thomas Pink but are great for the price.

  2. DaveJ says:

    We were discussing cufflinks, and realized we did not know what the back was called. Since they have a name for aglets, they must have a name for the backs of cufflinks (other than #%$^% foldy thing.) don't you think?


  3. liz says:

    I was not aware that themed cufflinks were a "NO-NO" I have bought my husband a few and I always thought they were wonderful! LOL and he gets tons of compliments on them. hhmmm… good to know…

    • Jamie says:

      Telling your wife you don't like a gift is probably also a no-no :)Generally those accessories like that, you want to go with a classic look. Especially when you're talking more formal accessories.

  4. Naomi says:

    So which kind of shirt shoukd be bought to be worn with cufflinks? most of them have buttons…

  5. Procuffs says:

    On reading this post I wanna just say only Excellent work!

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