If you've taken a lap around the Pentagon, you know men regularly and spectacularly fail to select appropriate and flattering dress shirts. Despite their seeming simplicity, dress shirts are surprisingly complex and like every other element of menswear take time to master. With that in mind, I'm going to share my advice for building a dress shirt collection from the ground up. As with all my advice, this is designed for a formal work environment and approaches the problem from a classic menswear paradigm.
To make this as digestible as possible, we're going to break down each element of the dress shirt and discuss them individually, starting with color and pattern.
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Dress Shirt Color and Pattern
Beginner Dress Shirt Colors
There are three essential shirt colors when building your shirting wardrobe: white, light blue, and light blue Bengal stripes. I recommend purchasing two or three of each as the building block for your wardrobe.
Intermediate Dress Shirt Colors
After you have several white, light blue, and light blue Bengal stripe dress shirts, other light, desaturated solids like light pink and ecru can be appealing shirting options. Bengal stripes in a variety of other colors including navy, brown, pink, and gray are also good choices. Other striped patterns such as reverse, pen, and pencil stripes in the above colors are also an option.
Advanced Dress Shirt Colors
The shirt patterns and color in the beginner and intermediate categories are enough for any shirting wardrobe, but if you want to experiment more, shadow, awning, and border stripes are now viable patterns. You can also expand the color range of your striped (not solid!) shirts to include green, yellow, red, and purple.
I want to emphasize that these are intermediate or advanced shirting options and recommend everyone start with a rotation of white, light blue, and light blue stripes until you develop a stronger sense of your personal style. I strongly argue for this approach because of the seriously ill-considered dress shirts we often see men wear, the most common cases of which I'll explore now.
Dress Shirt Colors to Avoid
Dress shirts work best when they are lighter than the jacket or tie and desaturated. Unfortunately, many men are drawn to dark, saturated dress shirts. Forest green, burgundy, black, chocolate, cobalt blue, and French blue (the color of the dress shirt every boy's mother bought for their first shirt) should all be avoided.
Not everyone agrees on this, but I would also recommend you avoid checked dress shirts of any kind. They are too visually complicated and attract attention you would rather have devoted to other parts of your outfit. And yes, this includes gingham, which is a fine, if somewhat preppy, casual shirting, but too informal for wear with a tie and jacket.
Dress Shirt Collars
Besides the color and pattern of your dress shirt, the collar is the next most noticeable feature. There are three most important aspects of a shirt collar: fit, shape, and ensuring the collar points sit under the lapels of your jacket--the shape of the collar being an important factor in facilitating this.
How Should a Dress Shirt Collar Fit?
Shirt collar fit is rather simple. The collar should fit around the neck without showing any gaps or being so tight that the skin of the neck bulges out over the top of the collar. Measuring you shirt size is easy too, just take a cloth measuring tape and wrap it around the base of your neck and you've got your collar size.
Dress Shirt Collar Shape
The three primary aspects of collar shape are firmness, length of collar points, and angle at which the collar points spread from the center of the collar. This last aspect determines the name of the collar shape, with the following collars all increasing in angle of spread: point, semi-spread, spread, and cutaway.
From left to right: cutaway, spread, semi-spread, and point collars
For business looks and beginners, I recommend spread collars, the most formal of the collar options and also the likeliest to keep your collar points nicely seated under your lapels. Cutaway collars are generally too aggressive and informal, but in their most moderate from can be worn with business attire if your aesthetic preference leans this way.
Most semi-spread collars available to purchase come with collar point that are far too short and leave the points floating in the middle of the shirt, not under the lapels. However, with long enough collar points, to ensure they stay under your lapels, semi-spread collars can be an acceptable, even attractive option. Point collar can feel a little too much like the 90s on a beginner, but are an option for advanced dressers and can look great in the right outfit.
The difference between these two collars, both semi-spread, effectively demonstrates the importance of long collar points. The collar points Franklin Semi-Spread on the left will struggle to stay under your jacket lapels, but the President Semi-Spread on the right should have no such problems.
Button-down collars get their name from the small button holding the collar point to the chest of the shirt. They are generally too informal for business wear, but are a staple of Americana and a great option for a casual shirt.
If you want to expand from your initial basic spread collars, I recommend going for a collar with long collar points and a bit of collar roll instead of a clean fold as the collar comes off your neck. Many brands call these collars Italian and are available in both spread and button-down version.
Top row: Spier and MacKay's large Italian spread and the large Italian button-down
Bottom Row: Proper Cloth's Roma Spread and Roma Soft Button-Down
Contrast Collars (and Cuffs)
Contrast collars and cuffs trace their history back nearly two centuries to when collars and cuffs were not a part of the shirt, but detachable. The collar and cuffs are always the dirtiest part of a shirt and being detachable made them easier to wash. The contrast collars and cuffs are attached but their white color makes them stand out, too much so actually. Unless you're purposefully recreating a vintage look, a contrast collar makes you look like you're cosplaying Wolf of Wall Street or American Psycho and should be avoided for that reason.
Dress Shirt Fusing
Dress shirt collars and cuffs are made of a top and bottom fabric layer and an interlining to give the collar some shape and structure. In fused collars, the top layer is glued and pressed giving a neat and formal appearance that's best for business dress shirts.
Collar pieces and interlining
Non-fused collars come in two types, one with a free-floating canvas of varying stiffness to give the collar some structure or no interlining at all. Some shirt manufacturers like Spier & MacKay offer level differ collar lining options (you just have to email and ask), but more often collars and cuffs are offered only in fused or soft options, like at Proper Cloth.
The Spier & MacKay Large Italian Spread Collar, fused on the right and their second-softest on the left.
Dress Shirt Cuff Styles
There are generally four types of shirt cuffs, each with a different shape and implied formality. In increasing levels of formality they are the square, barrel, mitered, and French cuff. The cuffs with buttons are also offered in two button versions, while the one button cuff is standard, a two button cuff is simply a personal preference that doesn't affect the formality of the cuff.
Many men are overly fond of the French cuff, which should only be worn for black or white tie and is not suited for business wear. The barrel cuff is most common and what I recommend for others. Let other aspects of your dress shirt draw attention, not an unusual cuff design.
From left to right: square, barrel, miter, and French cuffs
How Should a Dress Shirt Cuff Fit?
The two most important factor are cuff size and sleeve length. The standard guidance fro cuff size is 1.75 inches greater than your wrist, but this can vary some to account for your personal preference. What you're looking for is a cuff that is tight enough to prevent it from falling down onto your hand. You shouldn't be able to take off your shirt without undoing the cuff.
Sleeve length obviously plays an important role here too. The sleeve, when unbuttoned, should fall to the first knuckle on your thumb. This will allow you to move your arm without the cuff riding up your forearm.
Dress Shirt Construction (Placket, Pocket, Pleats, Darts, Yoke, and Buttons)
Well, we've hit the miscellaneous section of the guide, so I'll try to get through these smaller details quickly. A placket is the extra cloth folded back onto itself on the front to the shirt where the buttons run. This is done to reinforce the button holes and prevent them from tearing. Plackets also come in fused or unfused varieties.
From left to right: front, French, and covered plackets
There are a few options for plackets. Most standard is the front placket, this is what most of the shirts you own likely are. The French placket is just like the front placket, but the fabric is folded inside the shirt giving it a cleaner appearance. The covered placket adds an extra flap of fabric to cover the buttons completely. This is often seen on tuxedo shirts, but it's best to avoid on normal dress shirts. I recommend a French placket on dress shirts and a front placket on casual shirts.
Crow's foot button stitching, seen here on a jacket cuff
Dress shirts look more formal when they have a neater appearance and for this reason, I also recommend omitting a pocket from the front of your shirt and pleats, either box or side, from the back of the shirt. A split yoke adds strength to the back of a shirt, and I recommend it for this reason. There are two things to say about buttons: first, mother of pearl buttons are the gold standard and worth the small upcharge and second, it's best to have you buttons attached with crow's foot stitching, which is not only aesthetically pleasing but also sturdier than normal button stitching.
Dress Shirt Fabric Options
There are hundreds of different fabrics to choose from when commissioning a dress shirt, so I'm going to keep this to basics. Generally the less texture and the thinner the fabric, the more formal it is. Broadcloth and poplin, technically distinct but barely so, are the most formal fabrics. The downside is that they can be somewhat fragile and in white even a little transparent.
From left to right: poplin, broadcloth, and twill
Twill, identified by its diagonal weave, is stronger and slightly less formal, but also less transparent and good option for white dress shirts. Other fabrics considered formal such as royal oxford, herringbone, and dobby are best avoided because they are too textured and draw too much attention to have a balanced outfit. Other fabrics like seersucker, linen, and oxford cloth are attractive, but best left for casual shirts. If you're buying a dress shirt, I recommend you stick to poplin, broadcloth or twill.
From left to right: seersucker, linen, and oxford cloth
How Many Dress Shirts Should You Buy?
I recommend buying two or three white, light blue, and light blue Bengal stripe dress shirts to begin. After that you can add a more interesting design one shirt at a time until you have a broad collection. Just remember the fewer dress shirts you have the sooner they'll wear out. Dress shirt lifespans should be thought about in terms of wears and washes, there is a limited number of each that any shirt will support.
Best Places to Buy Dress Shirts
When you're first starting out, it's important to conserve your money and not spend too much early as your tastes will change. If you follow this guide, you should be well off, but nonetheless, it's best to purchase value, not luxury shirts at first. With that in mind, Spier & MacKay is the clear standout. Their dress shirts start at $58 and drop to $48 if you buy three or more. If you can't find something you like there, Suitsupply also has attractive dress shirts, but they will be closer to $100.
Ready-to-Wear of Made-to-Measure Dress Shirts?
Dress shirts are one of the few items I recommend you immediately begin purchasing as made-to-measure. Ready-to-wear shirts rarely fit anyone well and made-to-measure shirts not only fit better, but are not really any more expensive than the ready-to-wear options. You can measure yourself at home and most shops offer instructions on how to record each measurement properly.
There are two brands to consider, Spier & MacKay or Proper Cloth. Spier & MacKay is more affordable, starting at $79/shirt and they offer a bundle discount of $10 off each shirt when purchasing three or more. I prefer their collars and their shirtmaker can alter nearly every aspect of the shirt, but you can't select these options in the ordering process, they must be requested later. Spier & MacKay also has a smaller fabric selection.
Proper Cloth has a wider variety of fabrics and offers greater transparency in the ordering process, any customization available can be selected while ordering, but is more expensive with most shirt fabrics costing $90 or more and no bundle discount and lacks some more advanced customizations, sleeve pitch alterations being just one example.
Both have excellent customer service. If you order more than one shirt from Spier & MacKay reply to you order confirmation and ask to have them send only one shirt so you can make adjustments that will apply to the rest. Trust me, it's better to wait longer to get your shirts by using this message, than to have all of them arrive and they don't fit.
For 20% your first purchase from Spier & MacKay, use this link.
For 20% your first purchase from Proper Cloth, use this link.
I hope this guide has been useful to you. I know I could have saved a lot of heartache and money if I had read something similar before starting to buy dress shirts a few years ago. As always, I'm available via DM or email if you have any questions about this topic or any other. If you liked the guide, please consider sharing it with anyone who might also benefit from reading it.