Consider the turtleneck. It’s a statement, for sure—and not the easiest one to make without verging on creepy Euro-beanik, or for lack of a better word: dweeby.

The trick is to avoid some common pitfalls—wearing something too gauzy, too tight or with a maniacally steadfast gaze. There’s a sweet spot in the middle there. And we’re going to help you find it, by taking some subtle cues from some of the most stylish guys to ever do it.

And now, a master class in the turtleneck, courtesy of five icons of style.

Dean Martin: This one’s easy: throw a blazer over it, grab a rocks glass and, at all costs, avoid anything that makes you look like a first-year assistant professor at Cambridge.

Simon & Garfunkel: These guys could’ve ended up looking like a couple of dweebs, but the commitment is what gives them the edge here. It’s their own brand of “morose swagger” and they’re owning it. Lesson: you’ve got to have the right attitude going in.

Marlon Brando: Here’s a great example of choosing one’s turtleneck wisely. Brando finds himself one without too much turtle in the neck so he can keep it folded neatly just above his collar. You’ll want to do this if your turtleneck is more shirt-like.

Ralph Lauren: This might be the highest degree of difficulty—a full suit with a turtleneck. Here’s where you could veer into creepy lounge-lizard territory, so steer clear of any smoky bars (and keep the leering to a minimum).

Michael Fassbender: This is a bit European by default, but it’s a great example of incorporating the turtleneck into a casual look. Throw on some shades and a jacket and keep your neck toasty. Sometimes it’s that simple.

—N.B.

CONTRIBUTORS

  • Najib Benouar