Before the Milk Tray man, before the decade that fashion forgot and then remembered (that’s the 1970s, in case you were wondering) and before Steve Jobs, the humble roll neck was already at work, establishing itself as a cosy but cool way of styling out the cold.

A modern wardrobe staple with all the comfort of a crew neck sweat, but with the added benefit of being considerably smarter, it’s fully earned its spot in the menswear hall of fame. “The roll neck jumper is a timeless classic thanks to its versatility and the fact that it’s extremely comfortable,” says male model and photographer Chris John Millington.

It’s become a staple of the front row set at Fashion Week in recent years, but it’s also retained a rugged masculine appeal (Daniel Craig’s Bond is a fan, for example). “They offer that Steve McQueen ‘man’s man’ feel that’s always appealing, but also provide the modern, refined look that men want right now,” says Alex Field, head of menswear design at Reiss.

History Of The Roll Neck

The exact origins of the roll neck are as murky as the name itself (on the other side of the pond it’s more readily referred to as a ‘turtleneck’, while ‘polo neck’ is another frequently used term).

Whatever your preferred moniker, the consensus is that it came into being during the 15th century, meaning this natty piece of knitwear has been around in one form or another for at least 500 years.

Like much of menswear’s clothing canon, the roll neck was born out of utility, initially worn by menial workers, sailors and naval officers before being adopted by everyone from poets and professors to playboys and prepsters.

Despite the wide-ranging appeal of the northward-creeping neckline, it only earned its place as a bona fide wardrobe staple as recently as 50 years ago. It was 1968, a time when the roll neck had all the sartorial star power of a pair of Crocs. Enter Steve McQueen as a straight-talking police detective in Bullitt and, suddenly, every man was clamouring to add one to their collection.

Steve McQueen wearing a roll neck as Frank Bullitt in Bullitt

Types Of Roll Neck

Perhaps even more confusing than the vagaries in the name are the differing types of roll neck available. Alongside classic styles it’s quite common to see a roll neck that, well, doesn’t ‘roll’ at all, or iterations that are barely more than crew neck sweatshirt. Consider this your pullover primer.

Classic

The type of roll neck that has found favour with generations of stylish men is, not surprisingly, the most classic. Featuring an extended neckline that folds back on itself, the result is often the most formal, lending itself well to tailoring or under an overcoat.

The Best Roll Neck Jumpers For Men

River Island Navy ribbed muscle fit roll neck jumper - Click To BuyUniqlo CASHMERE TURTLE NECK LONG SLEEVE SWEATER - Click To BuyJOHN SMEDLEY Cherwell Merino Wool Rollneck Sweater - Click To BuyNN07 Andreas Honeycomb-Knit Virgin Wool Rollneck Sweater - Click To Buy

Funnel Neck

A simpler variant of the classic roll neck, the funnel neck style is cut with a slightly shorter extended neckline, removing the need to fold back on itself. To give structure, most funnel neck designs are ribbed, but they can also borrow from athletic apparel by incorporating a zip.

The Best Funnel Neck Jumpers For Men

H&M Knitted turtleneck jumper - Click To BuySELECTED HOMME Brown High Neck Jumper - Click To BuyReiss ARMOUR FUNNEL NECK JUMPER - Click To BuySTONE ISLAND Wool-Blend Sweater - Click To Buy

Mock Neck

A hybrid of the funnel neck and crew neck sweatshirt, a mock neck knit locks in warmth with a slightly extended neckline. Best worn casually in a mid-weight, it’s the perfect way to add extra insulation to a winter look.

The Best Mock Neck Jumpers For Men

YMC MONTAND TURTLE NECK - Click To BuyTopman Black And White Turtle Neck Jumper - Click To BuyMango Wool-blend knit sweater - Click To BuyH&M Knitted mohair-blend jumper - Click To Buy

Know Your Gauges

Before fully warming to this refined, draft-excluding design it’s important to get a handle on the different types of gauges available (that’s the number of stitches per inch of fabric), which will impact not only its insulating abilities but also what it can be worn with.

Fine

Lightweight and form-fitting, a fine-gauge roll neck is the ideal piece to slip beneath a whole wardrobe’s worth of cold-weather staples. Smart enough to substitute for a formal shirt, particularly in temperature-regulating and breathable merino wool, it also looks just as good worn under a leather biker jacket for a faultless up-down combo.

The not so wonderful news is that there’s nothing like second-skin fabric for highlighting a gym-dodger, so it’s wise to bulk up your fabric if you’re carrying a few extra pounds.

Fine Gauge Knitted Roll Neck Jumper for Men

Mid-Weight

A far friendlier option for the exercise-intolerant, a mid-weight roll neck can add inches of warmth while disguising a more portly physique.

Versatile enough to work with both smart and casual looks (and, ergo, smart-casual ones, too) the added heft not only dials up the thermostat, but also gives some gravitas to lighter colours such as beige.

Mid-Weight Ribbed Roll Neck Jumper for Men

Heavy

Once a staple prized by men’s men like Ernest Shackleton and Hemingway, today a chunky fisherman-style roll neck retains its appeal for keeping its wearer toasty in the worst possible weather.

The undisputed king of insulation, a thick wool knit in a waffle or cable knit design is perfect for a frigid commute or when pounding the parks and pavements at the weekend, especially when slipped under an overcoat.

Heavy Gauge Cable Knit Roll Neck Jumper for Men

5 Ways To Wear A Roll Neck

Menswear’s ebb and flow may not be as mercurial as womenswear’s sometimes tidal seasonal shifts, but we get our fair share of difficult trends (kilts, anyone?).

For a long time, roll necks fell unfairly under this category, but you only need to look as far as the five examples below to dispel the misconception that they’re impossibly difficult to style.

Back To The 1970s

The seventies are going strong in menswear, and few pieces are as synonymous with the decade of Concorde, glam rock and Kevin Keegan’s hair as the roll neck.

To nail the look, opt for a mid-weight knit and experiment with tucking it into a pair of trousers before capping off with a shearling jacket for bonus points. Leave the flares at the back of your dad’s wardrobe.

How to wear a roll neck - 1970s inspired style

House of FraserSimonsRiver IslandRiver Island

Under A Leather Jacket

With a list of wearers that includes Sir Michael Caine and James Bond, the roll neck isn’t lacking when it comes to masculine credentials.

To amp up the testosterone further, layer a mid-to-thick gauge roll neck under a leather jacket and finish with tailored trousers for a look that can fly in a business-casual office, or jeans for the weekend.

How to wear a roll neck with a leather jacket

ReissCrombieSelected HommeMassimo Dutti

Under An Overcoat

Sometimes style and practicality are so hopelessly off-kilter that finding something that a) looks half-decent and b) is genuinely easy to wear, is just asking too much. However, when worn under an overcoat, a roll neck is an excellent way to brave low temperatures in high style.

For a smart outfit, anchor your top half with a pair of wool trousers and smart boots, or skew casual with chinos and sneakers for solid off-duty attire.

The best ways to wear a roll neck - underneath an overcoat

Selected HommeMango ManCrombieSelected Homme

With A Suit

Whether it’s for a casual Friday getup that looks good outside the office or as a way to tackle festive parties without having to truss up in a tux, a light-gauge roll neck is the perfect partner for a suit.

Neutral colours that contrast with the tailoring are a failsafe bet, so build a rotation of blacks, blues and earthy shades before attempting something more daring, such as jewel tones.

How to wear a roll or turtle neck with a suit or blazer

NextMassimo DuttiCharles TyrwhittSelected Homme

Layer Player

The roll neck’s greatest asset is its versatility, allowing certain styles to work just as well as part of a more dressed-down rig. But rather than with joggers and work boots in a homage to ‘Hotline Bling’, get creative with your layering instead.

A fine-gauge example can look surprisingly handsome under an Oxford shirt, while mid-gauge styles offer all the warmth of weightier versions when slotted under a gilet or overshirt.

The best ways to layer a roll neck

House of FraserOlzenRiver IslandZara