VI. Shirts

I have a confession to make, I once made a mess for a poor a Macy's associate. I had recently moved to the DC area and needed some new button-down shirts. None of the sizes fit. The result was a pile of unpackaged, unfolded, unpinned shirts in one of the dressing rooms that I casually left behind. As I’m dictating this paragraph, my wife—who worked in retail—is shooting me incredibly nasty looks. And justifiably so, that was a shitty thing to do.

Most mass market off the rack shirts fit precisely no one. They're either too big in one dimension, too small in another, or disproportionate based on the vagaries of the human form. For my chest size, the waist of an off the rack shirt is billowy, ballooning over my pants like a muffin. If I wanted to avoid that situation, I would instead risk popping buttons or choking. Finding a brand and fit of shirt is just as critical as designing the suit. Find a store where an associate can measure you and help you try on samples. The best option is to have a custom shirt made. The cost is higher, but resulting look can be well worth it. The choices you have to make for a custom shit is the topic of this chapter.

Materials

Some of the considerations for picking a suit material applies to shirts. Always avoid synthetic materials like polyester, don’t be a sweat monster. Linen is a great warm weather choice, but it wrinkles horribly and you'll look disheveled before lunch. Cotton is the material of choice. You'll want to make sure you try on a variety of weaves to find the one that feels right to you. Many of the shirts you'll find are blends, perhaps mixing in some synthetic fibers to reduce your ironing burden. I find that to be a reasonable trade-off. Ironing a purely cotton shirt is kind of obnoxious due to how easily it wrinkles in the wash.

Cuffs and Cufflinks

The first major aesthetic consideration is how your sleeves are going to close. There are two main options: buttons or French cuffs. The button cuff is relatively straightforward: you have one or two buttons (and usually one further up called a gauntlet button) that open and close the sleeve. A French cuff is more complicated, bending over itself and being fastened by a cufflink. Of the two, French cuffs are more formal and not something you often see. They're also harder to deal with when you want to roll up your sleeves, with the added bulk and additional items you have to keep on hand when doing so. I recommend button cuffs for those reasons. If you choose a French cuff shirt, you will need to obtain some cufflinks. They come in a variety of styles and colors with embossed features, jewels, and monograms. The choice is yours, just note that cufflinks count towards your accessory limit.

Collars

There are myriad collar variations, and you don't need to know the details of most. What you're looking for is pointed tips; there are informal collars with other shapes, but you want those triangular ends when suited. To keep them looking nice and prevent curling, they come with collar stays, either built-in or removable. Those are the common features of any shirt collar you’ll design.

Spread. This design element is the distance between the two points of the collar. It doesn't really matter what the spread is, but it does impact how you wear a tie. A wider spread will accommodate and look better with a larger tie knot and vice versa. Other than that, it doesn't really matter.

Length. The length of the points is another dimension. Longer collars tend to be old-fashioned. In the original Rocky, Carl Weathers wears a shirt with a very long collar, and that feels right for the 1970s.

Buttons. A subset of shirts will include buttons that allow you to affix the collar points to the shirt. These collars don't come with stays to keep the points pointy because the buttons do that for you. This style can provide a put-together look without being too flashy. However, it looks best when your shirt is fully buttoned up and you're wearing a tie. I would recommend unfastening the collar buttons if you’re not doing that, otherwise the top of the shirt will bunch-up that doesn’t look good.

Contrast Collar. We’ll get to colors and patterns shortly, but there's one that stands out specifically for the collar. The shirt collar used to be a separate item in a different color. A contrast collar continues this design aesthetic. It uses white fabric to provide, well, contrast. The look tends to be associated with executives, especially of the disreputable kind. Jeff Bridges’ character from Iron Man, for example, often wore a contrast collar shirt. That reputation doesn’t mean you should exclude it from your wardrobe. I recommend keeping it simple with a solid color shirt and only after you've established yourself. You don't want to be an intern sporting this look because, while it seems weird to say, you may not have earned the look. I also count a contrast collar towards the accessory limit.

Colors

Your shirt options are more varied compared to the suit. Almost any color can work. A good way to diversify your wardrobe on a budget is to have a relatively conservative suit and a variety of shirt colors and patterns. It would be a boring wardrobe to only have white shirts in your repertoire.

White. The most basic but flexible shirt color, white goes with anything. Think of a white shirt as a blank canvas that doesn't distract from and is used to highlight other aspects of your overall ensemble. Do you have an interesting pattern tie that would clash with other colors and shirt patterns? Then a white shirt would be a good option. You'll only want to wear a white shirt to a funeral, where it's most important to be monochromatic.

Cream. Off-white shirts are a good way to diversify while maintaining some universality. They add just a hint of color without being distracting, and they pair well with many other colors. A particularly good pairing would be a cream shirt with a brown suit. I'll put yellow shirts in this category as well, since they have similar aesthetic qualities.

Gray. A little less flexible than cream, but still within the universal family.

Blue. Having a couple blue shirts with some different weaves or patterns is a mainstay of any wardrobe. A light blue shirt will pair with almost any suit color and most ties. Dark blues are substantially less versatile and I don’t favor them.

Green. My recommendation is to stick to medium or darker greens, as lighter greens can be costumey and more appropriate for Saint Patrick's Day. You’ll have less pairing options than blue, but greens are overall solid choices.

Purple. Something more interesting to liven up your wardrobe, purple can make a fine addition to the rotation. Both dark and light purples work, but it's harder to pair a darker purple with the rest of your suit. Lighter purples like a lilac fit in the same role as light blues.

Pink. A surprisingly versatile color, pink goes well with many suit fabrics and ties. We're comfortably in the 21st century now, so concerns about masculinity should be moot. Have some confidence.

Red. A much bolder choice, and one that I don't recommend. The only time I ever wore a red shirt to work I received this comment from my boss, “wow very red.” It's difficult to pair a red shirt with the rest of your suit, and the psychological impact of red is the opposite of blue. Even though my nickname in high school was Redshirt Sam, my advice is to skip on this color.

Orange. Easier to wear than red, but unless you want to look like a pumpkin, I wouldn't recommend it.

Black. I've rarely seen a black shirt that looked good outside of entertainment. I respect the confidence it takes to attempt this look, but I don’t see a reason to include it in your professional wardrobe.

Patterns

Your flexibility with shirt patterns is substantial. The main consideration is whether your suit has a pattern. A solid suit can go with any shirt pattern. Even the most intricate geometric design will not be overwhelming when it's layered beneath a solid jacket. Things get dicey when you mix and match patterns. A striped shirt and a window pane suit may clash when worn together. Another maxim is to stick to two colors, especially if one of those colors is white; one of my favorite shirts is a dark green and white houndstooth. Three colors are the absolute limit. I only have one tricolor shirt, which has red and blue pin-width boxes over a white background. From a distance, the shirt appears purple on white, and the preponderance of the white background ensures that the close-up effect is not overwhelming. Ignoring these rules risks clownish territory.

You'll generally be safe with a geometric pattern. However, there are two that I can't recommend. The first is gingham: wide vertical and horizontal stripes resembling a tablecloth. The other is Bengal stripes, which are wide stripes of white and some other color that yields a circus tent aesthetic. Non-geometric images can work if they're arranged in a geometric pattern, such as small symbols in a regular array. Complicated designs are trickier, especially asymmetric prints, but you can get away with it if you follow the two-color rule. As long as your tie is relatively muted, only part of the complicated shirt will be poking out from underneath the jacket, which provides a nice accent rather than an overwhelming display.

Miscellaneous Elements

The extra details available for shirts are typically minor compared to ensuring a proper fit and the major elements we’ve discussed thus far. They will still arise during your shopping experience, especially if you’re having a custom shirt made, so you may as well be familiar with the options.

Placket. The placket is the front part of the shirt wherein the buttons live. There are only two variants that you need to worry about. The first is the standard placket, which includes an extra layer of fabric behind the buttons to help support them and add an additional design element. Pretty much every dress shirt you find will have it. The other form doesn’t include any extra material, creating a, in my opinion, casual look. I don’t prefer the placketless shirt because it seems incomplete.

Pleats. The back of the shirt can have either one pleat, two pleats, or no pleats. My recommendations is two pleats, because the extra material will facilitate movement and comfort.

Back Profile. A minor point, but you can choose the shape of the shirt at its bottom terminus, ranging from more circular to straighter. It really doesn’t matter, that part will be tucked in when you’re wearing a suit.

Sleeve Length. Part of your shirt fitting should include measurements of your arms to properly calibrate the sleeves. A good rule to follow is that the cuff should poke out from the suit sleeve and up to your wrist, so use that as your guide. Be sure to test it across your range of motion, you don’t want your arms to be immobilized because you cut the shirt sleeve too short.

Pocket. Shirts often have breast pockets, but they don’t have to. The lack of one can create a cleaner look, but it comes at the expense of one fewer storage option. I have shirts with both and it doesn’t make that much of a difference. If you’re going without a jacket, the extra pocket can be helpful for business cards.

Buttons. Light colored buttons go with most anything and are a safe choice. You can add texture too, but few will notice it. I typically go for two buttons on the cuff and no gauntlet buttons because it makes rolling up your sleeves easier and yield a better profile.

Undershirts

The button-down exposed to the world shouldn't be your only shirt. If you don't have an undershirt, you risk exposing yourself through the button down’s relatively sheer fabric. Your undershirt should always be white to avoid bleed-through. The tank top is a classic option, but I don't recommend it. I am a sweaty guy, and that is apparent any time I’ve tried to wear a tank top. The same is true for ordinary t-shirts. My only solution is to buy special t-shirts that have armpit reinforcement. Essentially, you cradle your pit in a cotton diaper to prevent it from bleeding through the shirt and, God forbid, the jacket. It's not as gross as it seems, because the same amount of liquid is leaving you, only it's better contained. This tactic is my recommendation, you just have to get used to the slightly different feel of the extra fabric.