How to go casual is not a problem with men. I never feel a compulsion to write about hoodies, jeans, sweatpants and sneakers because “As-Casually-As-Humanly-Possible” is a powerful and overwhelming chorus that doesn’t need another voice, no matter how many respected designers and luxury brands send them down the runway. As Bill Maher inimitably put it, our country won’t stop until we can hit the mall in Crocs and a diaper.

Put a guy in a situation like a beach, a gym or a JAY Z concert, and he can demonstrate uncanny sartorial appropriateness – even if he’s nowhere near a beach, a gym or a JAY Z concert. But send a guy an invitation to a black tie event and it’s like watching a dog walk on its hind legs.

Good black tie is one of the simplest yet most frequently misbegotten modes of men’s wear. One need only look at award show red carpets to see legions of celebrities dressed in unfortunate experimental remixes of formal wear. Many are mis-dressed by overpaid and misinformed stylists who get perks for having designers’ items worn by their clients, and the worst offenders are the ones who make ill-informed choices on their own. We can do better.

In well-chosen and well-tailored black tie, every man looks his very best. With roots in the military uniform, there is good reason that the tuxedo as we know it has remained essentially unchanged for decades: the simple and sublime form of the perfect tuxedo elevates a man to his most elegant self.

Bulletproof black tie starts with a black or midnight blue dinner jacket, commonly referred to as a tuxedo.

My black dinner jacket with peak lapels.

My black dinner jacket with peak lapels.

The jacket should have a peak lapel or a shawl collar. Notch lapels are for business suits. Single-breasted (one or two buttons) look great on everybody, while double-breasted jackets are generally the privilege of leaner, taller men. The dinner jacket can have a single vent, a double-vent or no vent at all. Like all jackets, it should conform to the body without squeezing it: snug in the shoulders, cinched at the waist. The length of the jacket should reach the thumb knuckles with arms relaxed at your sides. In other words… cover your butt.

Most men go too long with the jacket sleeves. Here’s the rule: the cuffs of a well-tailored jacket should expose one-quarter to one-half inch of shirt sleeve.

Closeup of dinner jacket with exposed shirt cuff. (The jacket will naturally expose more shirt cuff when you bend your arm.)

Closeup of dinner jacket with exposed shirt cuff. (The jacket will naturally expose more shirt cuff when you bend your arm.)

For shirts, avoid the wing collar, unless, of course, you’re dealing poker, serving wine or performing magic tricks. A fitted spread or semi-spread collar shirt with a nice cotton weave and French cuffs is the way to go. We men can get away with one tuxedo for our entire lives, but the well-prepared man might consider at least two tuxedo shirts in his arsenal. And I probably don’t need to mention this, but just in case: stick with white.

Aside from a nice watch, black tie is one of the few times a man can get away with fine jewelry without going too far. A handsome formal set of studs and cufflinks is the perfect finishing touch. Go with a silver set with onyx or mother of pearl.

One of my formal shirts, worn with onyx and silver formal set, and a cummerbund.

One of my formal shirts, worn with onyx and silver formal set, and a cummerbund.

Another common mistake, particularly among red carpet celebrities, is with the length of the pants. They’re often too long. Now there is a trend among the slim-fit hipster crowd to go super short and expose a bit of ankle. I’m a bit of a traditionalist in this area, especially with formal wear where we have rules. I like a little break where the pants at least touch the top of the shoe.

Black patent leather tuxedo "pumps."

Black patent leather tuxedo “pumps.”

And speaking of shoes… Traditional formal men’s footwear is a plain, patent leather shoe called a “pump.” Regular leather dress shoes can work, but make sure they are polished and buffed to shine like glass. Another great formal shoe option is the velvet slipper. Utterly understated and bafflingly elegant. The hard rule of the shoes is to keep them very plain, with no ornamental stitching or patterns like wing tip broguing. They should really never draw attention.

For the bow tie and cummerbund, a fine black silk or barathea does the trick. Many men don’t wear cummerbunds these days. I love them. They serve an often forgotten purpose by preventing the exposure of any shirt white below the jacket button. Just remember to keep the cummerbund vents facing upward.

As for the bow ties, no pre-tied nonsense, please. If you don’t know how to tie a bow tie, a salesman at your finer men’s shop can show you. And however fine or expensive, a regular necktie is never appropriate in formal wear. Ever. It just makes you look like a chauffeur or a very well-dressed pallbearer at a funeral. Black tie is a celebration. Wear a bow tie and celebrate!

James Bond is arguably the most well-known character in popular consciousness to wear black tie perfectly. I’d estimate that a lot of men would love to look like Daniel Craig in a dinner jacket. Unfortunately, one of the keys to looking like Daniel Craig in a tuxedo is to look like Daniel Craig out of a tuxedo.

Left: Daniel Craig in Tom Ford for Rolling Stone (photo by Matthew Rolston); Right: Daniel Craig in Casino Royale (© 2006 Eon Productions / MGM / Columbia Pictures)

Left: Daniel Craig in Tom Ford for Rolling Stone (photo by Matthew Rolston); Right: Daniel Craig in Casino Royale (© 2006 Eon Productions / MGM / Columbia Pictures)

For us civilians, the best way to level the playing field at a black tie affair is to observe the tried and true rules outlined above. Those same rules are used to dress Craig and also happen to be what author Ian Fleming, director Terence Young and bespoke tailor Anthony Sinclair employed to whip Sean Connery into shape for his dazzling black tie debut in Dr. No in 1962.

Sean Connery in Dr. No (1962), wearing a custom midnight navy shawl-collar dinner jacket by Anthony Sinclair

Sean Connery in Dr. No (1962), wearing a custom midnight navy shawl-collar dinner jacket by Anthony Sinclair

There you have the simple rules of smart black tie. The rules work. Fuck with them at your own risk.

A Follow-Up (or “Supplement”) to Black Tie 101: