One of the joys—or boredoms, depending on how you look at it—of dressing for formal occasions as a man is being largely immune to the demands of fashion. The tuxedo color is the same sober hue (black) that Sir Edward Bulwer-Lytton made essential for every well-dressed man in England with his 1828 novel Pelham; or Adventures of a Gentleman. Its cut has barely changed since the tailor for the Prince of Wales made one for American coffee baron James Brown Potter in 1886. Apparently, even radical innovations like velvet and bright-colored dinner jackets date back to the 1850s.
The contemporary formal shirt is more or less the same as it was in 1922, when Emily Post laid down the rules for black-and white-tie dress.
The shirt should have a gleaming white pleated or flat Marcella piqué front and matching collar. Both wing and turndown collars are technically acceptable, though the wing is seen as the traditionalist’s choice, and the turndown collar (as on a regular suit shirt) for those whose tastes run toward the moderne. The front should close with no more than four studs, preferably in onyx, silver, gold, or mother-of-pearl—although diamonds now pass inspection, too. The same goes for cuff links, whether the cuff is French or single.
In other words, change, when it comes, is a matter of inches and decades, not fashion seasons. The qualities that make a perfect formal shirt are in the details. Brooks Brothers has been making tuxedo shirts since it launched, and the classic version—a detachable wing collar held in place with brass studs, a piqué bib, and mother-of-pearl buttons—looks as good today as it did then. The innovation is the 120s fabric woven in Italy, softer than even the Prince of Wales could get. The downtown Manhattan boutique Seize sur Vingt offers a clean, stripped-down style, except for the pleats, which extend all the way down, making a cummerbund or waistcoat unnecessary and creating a long, slim fit that works with a single-breasted tuxedo or even a dark suit doing semiformal duty.
At Tom Ford’s eponymous clubhouse/den/New York store, a whole room is devoted to formal dress. There are even top hats for sale. The idea here is to construct your own version of the perfectly understated model: Choose a pleated or flat Marcella bib, then a wing or turndown collar, all rendered in handstitched, Swiss-milled cotton. Ford believes that unless you’re a rock star, you should stick with the simplest formalwear—though he does offer a very seventies ruffle-front shirt.
The très French house of Charvet is more than capable of making shirts in a classic style, with hand-pleated bib fronts and even detachable collars in impeccable white. But it also makes a shirt that looks a bit further back in menswear history, to when the aristocracy still embraced color and a certain exuberance of dress: It’s voile in pastels such as pale lavender, pearl gray, and pink. Co-owner Anne-Marie Colban isn’t old-fashioned, though. She prefers a shirt with a pleated front to one with a bib, and a turndown collar to the wing—it’s more comfortable for modern times, she says, adding that nothing looks better on a man than his being at ease with what he’s wearing.
And though the pink and lime-green body on Lilly Pulitzer’s tuxedo shirt seems anything but classic, pastels and stripes turn up under cutaway coats in illustrations from the thirties magazine Apparel Arts (the bible for classic-clothing aficionados), and men always went a little wild at the resorts. The shirt is cut so that it’s comfortable enough to wear with a quintessential peaked lapel, and the royal oxford bib happens to be white. Because a gentleman never removes his jacket when he’s out in public, Pulitzer’s überpreppy patterning could easily remain his little secret.
White or stripes, flat bib or pleats, wings or turndown collar, the most important element of the formal shirt is its finishing touch: a bow tie that you tie yourself. Don’t worry if it takes a while to get the last step—Beau Brummel, who is more or less responsible for the modern formal shirt, sometimes spent hours getting just the right insouciant knot in his.
The Houston-based, family-owned Hamilton Shirts has been at it since 1883. It’s a place where the rules of dress still apply. Co-owner David Hamilton, 30, deconstructs a cotton pleated formal shirt. $375; 713-780-8222; hamiltonshirts.com
The French cuff is, relatively speaking, a modern touch. It came of age at about the same time the Edwardian dandy did (roughly 1900). Besides being a way to show off black onyx links, this square French cuff is, according to Hamilton, the most formal of options. Baade II cuff links and studs, $650; 609-340-8650
The turndown collar with a medium spread is more unexpected than the wing style, says Hamilton. “This collar style is always more appropriate—and more flattering,” he explains. The company takes pride in catering to clients’ style specifications, so a wing collar is, of course, also available.
“They say a tuxedo shirt should be solid white or white with black detailing,” says Hamilton. “The man’s attire should not detract from his date’s ensemble.” This thin black stripe is subtle enough to satisfy that rule.
This cotton shirt with a turndown collar and mother-of-pearl buttons is a model of versatility: It would work just as well with a dark suit for a semiformal occasion as it would under a tuxedo. $395; 877-551-7257
When worn, this Whitehall shirt seems like any other beautifully made classic dinner shirt: solid white royal oxford bib, turndown collar, French cuffs. But when the jacket comes off, the Palm Beach pink and kelly-green gingham body makes it unmistakably Pulitzer. Lilly Pulitzer shirt, $250; 888-677-4261. Thomas Pink cuff knots, $10; 212-838-1928
Kabbaz-Kelly & Sons
Alexander Kabbaz made lightweight voile tuxedo shirts for Leonard Bernstein, who went through four per performance. Clearly this bespoke shirtmaker is happy to blend style with more practical concerns. Here, his most requested shirt, in Swiss-woven poplin with a turndown collar. $1,475; 631-267-7909
Designer Tomas Maier closed his fall show with two variations on white tie and tails. The year before, he deconstructed the tuxedo into sleek black trousers and a cashmere cardigan. Luckily, a shirt this beautifully classic works with all of the above. Piqué shirt, $550, and yellow Origami stud set, $10,110; 877-362-1715
Which of these is not like the other? Your eyes aren’t playing tricks on you: It’s pink. We know the rule about the white shirt, but Mel Gambert’s bespoke linen one is such a perfect pale shade of pink, it’s worth the risk. $425; 973-344-3440
It’s made from the finest Egyptian cotton and milled—naturally—in Italy. What makes this one different is the innovative flat-pleat bib. The signature Zegna touch is in the slim European fit. $450; 888-880-3462
Ralph Lauren Black Label
We turn to Ralph Lauren for pure, unadulterated tradition, and this cotton piqué formal shirt with French cuffs and handstitched button holes does not disappoint. $375; 888-475-7674