You have two very vivid memories of turtlenecks.
One of them involves you at a young age, and your mother mercilessly stuffing you into what could only have been described as the itchiest sweater on earth. You swore it was made of live fire ants.
The other is someone looking completely awful… wearing a turtleneck.
Let’s assuage those concerns now.
I can understand your trepidation, you remember turtlenecks as both uncomfortable at best and sartorial disasters at worst (and still uncomfortable). However, turtlenecks have come a long way from the ill-fitting, scratchy, too hot messes of your childhood. Modern iterations are slim fitting, elegant, and transformational. They can dress up any kit but they’re not stuffy, they’ve been edgy enough for artists, athletes, musicians, and rebels for the last half-century.
Since the 1950s turtlenecks have become a symbol of rebellion, a casual man’s substitute to the ubiquity of the shirt and tie. They were worn by men who wanted to dress both formally and roguishly. They’re extremely warm, versatile, comfortable, and best of all easy. If you can put on a shirt, that’s really all the expertise you’ll need. Turtlenecks take the guesswork out of matching. Instead of pairing a shirt with a tie and then to a jacket, you’re only pairing a turtleneck to the rest of your ensemble. You’re skipping a step, it’s much simpler that way.
Now if you’re still worried about possibly suffocating with what feels like a burlap sack wrapped tightly around your neck, realize that you have a choice now. Look for softer materials. Lambswool, angora, merino, mohair, and cashmere all have a much softer hand than wool. Try finding one of those. I recommend cashmere, remember it’s replacing both shirt and tie.