Turtleneck Outfits For Men: 8 Sophisticated Ways To Wear One

A 1970s style staple and now a hero piece of the modern man’s wardrobe, a roll neck can be a powerful tool… if you know how to use it.

A born layering piece with the ability to dress casual outfits up and smart outfits down, this high-necked contemporary classic is an absolute must in any man’s seasonal rotation. Warm, versatile and sharp, it can completely alter the overall feel of an ensemble when deployed with consideration. It will lend stuffy tailoring a relaxed edge, or give a simple trainers and jeans a sense of purpose.

The trouble is, while it looks great when worn right, it’s very easy to get wrong. To overlook it because of this, however, would be to do yourself a grave style disservice. Instead, stick to the following tried-and-tested looks and watch your winter wardrobe options open right up.

From weekend layers to workday tailoring, here are eight fail-safe ways to rock the season’s most transformative garment.

Knits On Knits

Brunello Cucinelli

Is it possible to have too much texture in an outfit? Well, yes. The moment things start to stick to you like velcro any time you sit down you can probably assume you’ve taken tactile dressing a bit too far.

However, doubling down on your knitwear is not just acceptable, but advisable. Not only will it keep the chill at bay, but layering up with different thicknesses and textures will create depth and significantly boost your winter style credentials.

Always use thin-gauge knitwear underneath the chunkier stuff and never the other way round. A merino wool roll neck is a good place to start, slotted underneath a thicker shawl-collar cardigan and layered with some heavier wool outerwear. Keep the colour palette muted and neutral for maximum versatility.

Business Minimalist

Hackett London

We’ve never visited the offices of a Scandinavian contemporary architect, but we’d imagine they’re probably full of people wearing this sort of thing.

Clean, uncluttered and straight to the point, this simplistic outfit really showcases the roll neck as a focal piece, allowing it to completely alter the dynamic of the look. Sure, you could do the same thing with a crew neck, but it wouldn’t look anywhere near as sharp or considered.

Rule number one when going minimalist is to always tuck in at the waist and forgo a belt. For this reason it’s important to ensure your dress trousers are the perfect fit. If in doubt, pay your local tailor a visit. Top it off with black leather Derbies or loafers and seal the deal with a mac or trench coat when it’s time to venture outside.

Suit Separates

Brooks Brothers

When full-blown tailoring is too much but your smart-casual wardrobe just won’t cut it, suit separates are the way to go. Slick yet laid back, when you add a roll neck into the mix it’s the perfect look for anything from a winter wedding to date night.

Swapping the shirt for a fine-gauge roll neck in this instance alleviates any potential stuffiness for more informal settings. It also lends your tailoring a modern edge and an air of minimalism when accessories are kept to a minimum.

To pull it off, the most important thing is colour. Autumnal shades will always work well during the colder half of the year but can be a bit much if handled without restraint. A good jumping-off point is to have one coloured piece and keep everything else pared-back. A beige or camel knit teamed with shades of grey is a timeless and refined combination.

Weekend With Bomber

Brunello Cucinelli

The bomber jacket is nothing short of an outerwear hero, but its short knitted collar isn’t particularly well suited to deflecting frigid temperatures. The solution: team it up with a roll neck to achieve good looks and full insulation in one fell swoop.

This look is perfect for wintery weekends out. It’s comfortable and low-key, but without looking sloppy or thrown together.

From the ground up, boots or sneakers will both work well depending on the weather. If it’s icy and wet opt for the former of the two with a nice thick tread – a Vibram-soled Derby or Chelsea boot would work nicely. When it comes to trousers, jeans and chinos are both solid options. Just make sure there’s some contrast in there, whether it be from the jacket, the roll neck or something else.

Statement Overcoat


There’s a nifty trick to excellent winter dressing. It’s simple, effective and, like all good things, it involves a big coat.

Using minimalist basics and a tonal colour palette to anchor an outfit then deploying some statement outerwear to serve as a focal point is a tried-and-tested recipe for sartorial success. Using simple black pieces to serve as a backdrop allows you to get really adventurous with your choice of coat or jacket.

Start off with a thin black roll neck and black dress pants. Next, add in your footwear – black again of course. It’s impossible to go wrong with a classic Chelsea boot. In terms of outerwear, don’t be scared to let a bit of personality shine through, but something like a check or houndstooth wool overcoat will always be a safe and versatile choice.

Casual Layering

Massimo Dutti

There are few, if any, things that don’t look great when teamed up with a nice overshirt and some casual outerwear. A roll neck, as it turns out, is no exception.

When you’re stuck for what to wear on cold weekends, a roll-neck-and-overshirt combo is ideal as a go-to; something you can simply throw on without a second’s thought, safe in the knowledge it’ll look good and work in pretty much any setting.

To keep things more towards the smart-casual end of the spectrum, wear it with dress pants and leather boots. Feel free to get creative with the colour scheme, but as a rule of thumb, earthy tones and autumnal shades generally tend to be crowd pleasers.

With A Suit


One of the roll neck’s key selling points is its ability to completely change the overall look of an outfit. Nowhere is this more evident than when it’s worn in place of a shirt with tailoring.

This is an ideal autumn and winter option that can help to bring a touch of flair and personality to an otherwise simple suit. Just make sure to select a fine-gauge knit so that it slots neatly beneath your jacket without restricting movement.

In terms of colours, keep things two-tone. Black knitwear and grey tailoring, for example. Or a navy suit with a charcoal roll neck. Top it off with some black leather Derbies and you’re good to go.

Leather Outerwear


In terms of looks, leather jackets and roll necks don’t have a great deal in common. When it comes to rock ‘n’ roll attitude and making you look a little bit cool and French, however, they’re two peas in a stylish pod.

Alone, they’re powerful enough but when worn together a leather jacket and a roll neck sweater are an unstoppable force. Any style of jacket will work, but we’d recommend either a classic biker or a shearling-collar aviator. Either way, make sure it’s black.

For the knitwear, either keep it tonal or in grey and combine with black jeans, boots and a hearty dose of swagger.

Paddy Maddison

Paddy Maddison is Ape's Style Editor. His work has been published in Esquire, Men’s Health, ShortList, The Independent and more. An outerwear and sneaker fanatic, his finger is firmly on the pulse for the latest trends, while always maintaining an interest in classic style.