In short; Carefully. The right roll-neck, worn well is one of the most elegant and masculine pieces of clothing you can own. They’re also one of the easiest pieces of clothing to get wrong and when they’re not worn well, they look heinous.
The most important point for wearing a roll-neck well is texture, by finding parallels in the rest of your clothing to the texture and feel of the roll-neck. Like all knitwear, there’s significant diversity in weights, thickness, pattern and fit, which you either consciously or unconsciously weigh up when choosing what to wear, but the prominence of the neck in a roll-neck makes it stand out so much more than other knitwear, making it a focal point of anything you wear it with (for good or ill).
A simple navy crew-neck sweater typically disappears into an outfit, which is a good thing if it harmonises with the rest of what you’re wearing, meaning you look imperceptibly well dressed and nothing more (a good thing). But a simple navy roll-neck will always stand out, due to the prominence of the high-neck. So the goal then becomes to accept that it will be more noticeable than most other items you’ll wear and then make sure the rest of the outfit compliments and anchors that choice and the easiest way to do that is through texture.
Like any other form of knitwear, roll-necks work from mild weather through to freezing temperatures. If it’s mid-winter and you’re in the snow, a chunky cashmere roll-neck worn with faded jeans, storm-welted boots and a good jacket is one of the warmest choices available (the roll neck does a much better job of warming your neck than a scarf). At this point, cable knits, heavier gauges and plenty of body all compliment the ruggedness of jeans and boots. In the image above I’m wearing my fairly well beaten up Barbour Steve McQueen motorcycle jacket, a pair of old selvedge Levi’s and a chunky roll-neck form the Aran Isles (way too itchy though, more on that below) with a pair of cashmere lined suede gloves from my favourite glove shop anywhere, Luciano Gloves in Florence. A thin, lightweight roll-neck doesn’t work here, you need more body and texture to bring everything together. Nothing in the image stands out on it’s own (except for maybe the richness of the blue in the roll-neck; a darker navy would be better).
Conversely, a lighter weight roll-neck is better suited to being worn with tailoring. The thinner, less textured knit needs more refined cloths for it to work well. In the image above, taken at Dolce and Gabbana’s Sartoria last year, the black roll-neck suits the simplicity of grey wool trousers, calf loafers and the bespoke Loro Piana cashmere overcoat from Bijan. The image below is from our visit to Corgi in Wales (taken around the same time). In that image, I’m also wearing a black cardigan (same weight and knit) over the roll-neck for an extra layer of warmth (Welsh knitwear factories aren’t the warmest places, it turns out).
Weight: One area of caution is around your weight or body shape. Lightweight roll-necks look best when worn close to the body (the fitted look around the neck looks best when extended throughout the rest of the sweater). If you’re carrying any extra weight, a reasonably fitted and thinner roll neck will expose it immediately. Given that most men put weight on first at their stomach, anyone other than an athlete risks looking like they’re carrying a spare tyre. To get around this, leave it untucked and sitting just below your belt line. The look is still clean and elegant, but gives a reprieve for any weight accumulated above the hips. If you’re built like an athlete, then tuck away. Once you move on to thicker knits, the issue is lessened as the thickness of the knit hides details (and you wouldn’t tuck a thick knit in anyway).
Fabric: Choose either a high quality (very fine) merino wool, cashmere or, if you can find and afford it, Vicuna. Anything which isn’t soft to the touch will irritate the hell out of your neck. With most other knitwear, it doesn’t spend much time in direct contact with the skin (you’ll have a polo or t-shirt on under a jumper) so the knit can be less soft and you won’t really notice it, but it’ll drive you mad with a roll-neck. Because the fabric sits against the neck with no barrier and because the neck is a sensitive part of the body, if the fabric isn’t soft you have no way to get around it, so choose wisely or you’ll never want to wear it.
The other option is to ignore all that advice and just be Francesco Maglia (below), wear whatever the hell you like and still be fabulous. Up to you.