Menswear moves slowly, incrementally, like poured concrete or the plot development on The Killing. And men’s formalwear moves slowest of all. The fundamentals of black tie have, for the most part, remained exactly the same for the past six decades or so. Which is great, because it means that the tuxedos our most iconic leading men were wearing 20 to 50 years ago are still very much relevant today. Here’s what you can learn from them.

DOUBLE UP

Humphrey Bogart

The double-breasted silhouette is in the midst of a roaring comeback, but as of yet, the revival hasn’t stretched very far into the realm of black tie. It’s time for that to change.

Bogie knew it best: a smartly buttoned-up double-breasted tux inspires a great deal of poise in its wearer. You’ll stand up straighter, feel more assertive, and look more sophisticated than ever. And, for the time being, you’re likely to be the only man in the room wearing one. Take advantage before that’s no longer the case.

STAY PROPORTIONATE

Sammy Davis Jr.

There are two important rules to be gleaned from this wonderfully candid snapshot of Sammy Davis Jr. and his mother at a 1966 Friars Club dinner held in his honour:

1. When it comes to tuxedos, proportions are everything. If you’ve gone for slimmer lapels on your jacket, as Sammy has here, then your bowtie should be equally svelte. One should never be noticeably wider than the other.

2. Bringing your mom as your date? Always a classy move.

DON’T FORGET YOUR SHADES

Jack Nicholson

Accessorizing black tie is tricky business. Venture too far beyond the traditional boundaries—basically anything outside a simple white hanky, slim dress watch or fresh boutonniere—and you risk breaking up the clean, classic aesthetic.

A great pair of sunglasses, though—those are always in play. Whether you opt for aviators, wayfarers or vintage keyhole frames like Jack does here, showing up in shades will elevate your tux’s cool factor tenfold. Just remember one thing: Unless you’re Nicholson himself, keep them in your breast pocket indoors.

NUIT BLANCHE

Bryan Ferry

A white dinner jacket comes with inherent risk. You might spill a spot of bisque on the lapel, or worse, be mistaken for the maître d’.

But the reward? One glance at Bryan Ferry in all his nonchalant glory should make it patently clear. Worn with confidence and grace, an ivory jacket is more than just stylish—it’s sublime, a gamble every inch worth taking. Just be sure to skip the soup.

BE YOURSELF

Paul Newman

One thing you’ll note in all of these photographs—most especially in this one, of the interminably cool Paul Newman—is that the men pictured look relaxed, at ease, comfortable. They look like themselves. And that’s not always an easy thing to do in a tuxedo.

There’s a tendency to think of formalwear as just that: formal and stiff, a uniformed vacuum of personality. In truth, black tie’s simplicity forces you to show the world exactly what kind of man you are. Let yourself shine through, or it’ll swallow you whole.

More to the point: if you’re wearing a tux, there’s likely good reason to celebrate and let loose. Embrace it.