At various times, the classic white shirt has been denigrated as stodgy and yet used repeatedly by cool dudes with the top few buttons open to exemplify the height of refined male couture. When I went to work in NYC after business school in 1976, the white shirt was more the former than the latter. It was legendary that if you worked at IBM you had no choice, you had to wear a white shirt and it was heresy and career limiting to do otherwise. Of course those were also the days when business had just barely shed their need for the ubiquitous fedora to be properly dressed. Respectable shoes were black laced shoes and the concept of the loafer was for loafing on the weekend, decidedly not for the workplace. One of the great benefits of the white shirt was that no matter what tie the clumsy style-devoid male would select that morning, it would not clash with the white shirt. In fact, one of the great sartorial workplace insults was to say to some guy that his tie was so ugly that it was the only one you had ever seen that wouldn’t go with a white shirt.
Of course, white shirts come in all types with four elements at their core. First and foremost was the material. No self-respecting Wall Street guy would ever wear anything but 100% cotton (wash & wear notwithstanding), but cotton ranged from a heavy Brooks Brothers cloth that was almost a canvas to a fine and thin Italian polished cotton. The primary styles of dress shirt fabrics that are most common are Poplin, a lightweight, smooth fabric with a tight weave that is both crisp and formal with minimal texture, Oxford, which is sort of a basketweave texture that’s slightly heavier and more casual looking, but very durable and breathable, Pinpoint Oxford, a finer than regular Oxford but with similar texture that is a versatile middle ground between Oxford and Poplin, Twill, a distinctive diagonal weave pattern that creates a soft, draping fabric resistant to wrinkles, Broadcloth, a very smooth, flat appearance with high thread count and little texture that is more formal but can be less breathable, End-on-End, which is similar to Poplin but woven with alternating colored threads creating a heathered appearance, Chambray, a lightweight plain weave that resembles denim but is much finer and lighter, and Royal Oxford, an elevated version of Oxford with more sheen and texture that is more formal than regular Oxford. You can then go into the underlying fabric itself with linens (from flax fibers), Sea Island Cotton, Egyptian Cotton, and Pima/Supima Cotton, but those distinctions rarely reach the mind of the Willy Lomans of the working world.
Once you have your material, you need to focus on the collar, which is easily the most important element of any dress shirt. It is the interface between the suit, shirt, tie and face of the wearer. A bad collar is inexcusable and a good collar makes an outfit. Assuming away the more formal wing collars and such, the working man basically needs to choose between the long vertical collar and the horizontal spread collar. There are countless versions of both, but one thing is for certain, the only one that allows for a button-down is the long vertical version. I have always found that spread collars do OK with a tightly tied tie, but that button-down collars do equally well buttoned up or left open. It is clearly the low-risk, low-hassle way to go, which is why I have always chosen it, but it is also clear that those brave enough to pull off the open collar without buttons usually make sure their collar is well starched and their neck and chest well tanned. I lack that confidence so I stick to the button-down.
The next option has to do with the cuffs. You can either get buttoned cuffs, which are certainly viewed as less elegant and more work-a-day, or you can go with French cuffs that get folded back and then cuff linked to your wrist. I have perhaps fifty pairs of cuff links and there certainly was a time when I felt the need to dress up at work with French cuffs and baubles on my wrists, but the more confident I got in my work, the more I just went with the buttoned cuff on the theory that the worst I could be accused of was being a workhorse rather than a show pony. I always keep a few more formal shirts with French cuffs so that I can wear the more expensive pairs of cuff links in my vast collection. It always feels good to don the cuff links, but there is no mistaking the fact that this is not work, this is for show. I should add that for both collars and cuffs (regardless of style of either), it is critical that they be firm and crisp. In the old days this was done with lots a starch as the stiffener, but as time has gone by, shirt makers have added backing in both areas to stiffen the resolve of the collars and cuffs on a more or less permanent basis. Floppy and limp collars and cuffs are disgraceful and sloppy and should be avoided at all costs.
I know that some guys who are more svelt than me (that would be just about anyone) might like to have their shirts fitted with those vertical pleats down the back. I have always followed the Brooks Brothers rule of thumb and left myself plenty of billowy room to maneuver in my dress shirts. It is only noticeable when your jacket is off and then only the Tom Cruises of the world can make the fitted shirt work well for them. The rest of us stick with the comfort of a roomy cut.
Perhaps the last item on the option list, and it is really an option, is the monogram. It always seems cool at first to have a monogram. I have a good monogram with RAM, but the question immediately becomes where you place it and what color you get it in. Any way you look at it, a monogram is a statement of affectation. The standard place is at the top middle of the chest pocket. For those who eschew the shirt pocket (a big mistake in my opinion) a monogram on the chest is next. The shirt cuff is a popular spot for a monogram and after that it gets kinda weird. Some people put a monogram around their midsection, but I’m not sure what that says about the wearer. A monogram on the collar is also possible, but generally gets viewed as trying too hard. I stopped getting monograms years ago and do not own a shirt with one to this day. My shirts are all custom made so on the shirt tail they have my name in some form or another, usually on a tag with the date of manufacture of the shirt. That is all the identification I feel I need on my shirts.
For this trip I am leaving on tonight, I have packed a formal white shirt and a standard white shirt. The rest of my shirts are either light blue or some patterned blue or patterned black and white. I did this on purpose to maximize dressing flexibility since I need a wide array of formal, semi-formal, smart-casual and casual dress for the trip. I’m not sure I am the best arbiter of those styles under any circumstance, but I gave up long ago letting anyone else make my sartorial decisions for me. I have a high degree of confidence that I will be within 10% of the required zone on any of the categories and at the heart of it all is the always-reliable crisp white shirt.