Okay, so the word “turtleneck” may conjure up dorky images of Steve Jobs or Mike Brady. But hear us out: those high, tubular collars are a classic symbol of sophistication—you just need to know which ones to buy and how to pull them off. Heck, Roger Moore rocked the turtleneck and sports jacket combo all the time. You mean to tell us 007 didn’t have good fashion sense? We didn’t think so. So sit back and learn how to swaddle your neck in style.

BROOKS BROTHERS BLACK FLEECE CASHMERE TURTLENECK
Featured in the “Natty Professors” photo shoot from our December issue, Brooks Brothers’ Scottish cashmere turtleneck captures the Ivy League look without being overtly geeky. Excellent as a layering piece, this slim-fitting sweater works best under a suit jacket or cardigan—but be sure to stick with solid colours. A smart-casual style for those who wish to look more Steve McQueen and less Stephen Hawking. $515, brooksbrothers.com

GAP CABLE KNIT TURTLENECK SWEATER
You know who wore the hell out of a turtleneck? Earnest Hemingway. This cable knit number from Gap updates the author’s rugged, yet dignified, manly style. It’s not overtly nautical, but it’s got enough seafaring flavour to give off an explorer vibe. And that’s a good thing. $70, gapcanada.ca

RALPH LAUREN MERINO SUEDE-PATCH TURTLENECK
Tired of the jacket-and-tie monkey suit? A turtleneck can act as an excellent alternative, as long as it clings close to the body. This 100% merino wool piece from Ralph Lauren is a prime example; it offers a strikingly elegant look in one understated, snug piece, accented with sumptuous suede patches. Pair it with dress pants and you’ll be one suave, cozy son of a gun. $279, ralphlauren.com

ACNE ALP POLONECK
There’s no edict in the Fashion Bible commanding that all turtlenecks be skin-tight. Take, for instance, this loose and drapey merino wool sweater from Swedish brand Acne. The slackened piece has stripes that have been knitted in different directions, giving the turtleneck a free, laid-back texture and tone. Team it with bleach white jeans for a cool, unflappable vibe that’ll make Snoop Dogg look like Colin Powell. $240, shop.acnestudios.com

VERSACE COLLECTION ZIP DETAIL TURTLENECK
Some fellers love a partial reveal—like a movie trailer that gives away only a tiny snippet of an epic blockbuster. This is the turtleneck equivalent of that trailer. At first, you get a simple black turtleneck with an angled zipper detail. But pull the zipper back and it slightly reveals a grayish-black lining, creating a sexy contrast. And you thought turtlenecks were rated PG. $200, versace.com

HUGO BOSS SLIM FIT T-NECK SWEATER
In the late ‘60s, a turtleneck with a sports coat was virtually a uniform among advertising art directors. Nowadays, that combo’s all the rage once again (thank you Mad Men and cyclical fashion trends). To achieve this look, a lightweight neutral like Hugo Boss’s silk/cashmere turtleneck is paramount. Pair this finely knit, ottoman-detailed pullover with monochromatic colors. It’ll be the coolest get-up this side of Sterling Cooper Draper Pryce. $325, hugoboss.com