The classic turtleneck (or rollneck) has an interesting and alternating fashion history in the United States. It was commonplace and cool in the 1950s and ’60s, worn by everyone from beatniks to musicians to movie stars like Steve McQueen. Then, there was a period when wearing one seemed stuffy or archaic—almost as dated-looking as bell bottoms or an early 80s newscaster.
The Best Fisherman Sweaters Go With EverythingDon’t know what to wear? Just throw on a cable-knit.
But, as with all things of value and substance, time has been kind to our neck-warming knit, and it has become a closet staple for good reason. It instantly elevates any casual outfit and can be substituted for a dress shirt on almost any occasion. It is inherently elegant and its elongated silhouette is flattering to all body types. Heck, wear a turtleneck under or over a collared shirt (more on that advanced style swerve below).
Today, there are so many ways to wear a turtleneck, and pretty much all of them work. While we love a cable knit or chunky, fisherman’s rollneck, the focus here is mainly on thinner merino or finer gauge cashmere turtlenecks and the various ways they can be worn. Here, we break it down for you.
There is a simple, chic elegance to a solid turtleneck worn on its own. It immediately adds sophistication to even the most lovingly well-worn denim or casual chinos. While you can never go wrong with classic navy, black, or charcoal, experiment with the myriad of colors out there to inject more personality. Feel free to wear the neck more scrunchy or aloof, letting it lay on its own. Pair it with brogue boots that have a hard-earned patina or classicwhite sneakers— it all works.
Underneath a Blazer
The amazing thing about a turtleneck is that it is essentially winter’s counterpart to a summer oxford or polo shirt. It holds its own just as classically underneath a blazer as a more common collared shirt does, thanks to its inherent formality. Wear it with an open double-breasted blazer for some swag, or button up a single-breasted notch lapel. Just be sure to fold the neck down or keep it neat-looking to compliment the tailoring.
Underneath a Casual Denim or Suede Jacket
A turtleneck will instantly add some refinement when paired with a denim jacket, suede jacket (we’re looking at you, John Lennon circa Rubber Soul), or even a puffer or M65 field jacket. We meant it when we said versatility. A roll neck, which fits somewhere lengthwise between a turtleneck and crewneck, works well here due to its inherent rugged nature.
With a Suit or Formal Wear
Holiday events or winter weddings? No problem. A turtleneck is as elegant a suit underpinning as a more classic shirt/tie combination. We have seen this look on everyone from 60’s icons to current stars on the red carpet. A turtleneck will also add extra refinement to a dinner jacket or velvet ensemble. Just be sure it is made of merino wool or fine gauge cashmere to allow the suit to fit your body, and, as with a blazer look, keep the neck folded and/or neat.
Three Ways to Pull Off a Suit This Holiday Season, All Under $1,000A little tailoring never hurt nobody
Underneath a Collared Shirt (Advanced)
A turtleneck under a collared shirt not only adds an interesting aesthetic layer but also essentially replaces a scarf. Try it under a chambray or flannel shirt for a winter workwear look, or under a crisp dress shirt and blazer to add an extra layer of bundled-up elegance. Just make sure the turtleneck is tucked into your trousers, allowing the shirt or blazer to shine. Leaving it untucked might appear sloppy.
A Collared Shirt Underneath (Expert)
When I was an editor at Esquire, I was intrigued and inspired one day when I noticed the impeccably dressed Fashion Director wearing a turtleneck, but with a subtle pop of a collared shirt emerging from the neckline. Alas, it is an insider’s advanced swerve that adds a rakish, preppy element to the look— an elegantly and intentionally disheveled touch. To pull this off, you need, first and foremost, a level of confidence and innate style, which we know you can possess. Second, ensure that the dress shirt collar is not too stiff and just slightly pokes out over the top of the neck. A chambray or oxford shirt works best due to its inherent informality and fluidity. If you can pull it off, you will be the most in-the-know guy in the room. Good luck!
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