When I manage to squeeze my head through the neck of my gray turtleneck, pull on some slim trousers and throw my hair in a loose bun, I feel like the most intellectual-chic girl in the world. Turtlenecks have seen their ups and downs throughout the modern Western fashion era, serving a utilitarian purpose until the 1900s when they became a fashion statement, associated with preps and intellectuals by mid-century. Today, they’re about as mainstream as it gets. And yes, you can wear them without looking like your aunt in the eighties.

The first documented appearance of the turtleneck was during the medieval era when knights would layer turtlenecks under their chainmail to prevent chafing. The turtleneck as we know it today was first worn in the late 1800s by polo players, from which the English name for the style, polo neck, was derived. Turtlenecks strayed away from their strictly functional uses and gained traction in the fashion world at the turn of the 20th century when they became a staple of the elegant Gibson Girl look (only complete with the hair, of course), and became a regular part of unisex fashion by mid 20th century. In the 50s it was tight and trim. By the 90s it was baggy and cozy. The most iconic turtleneck look? Unarguably Audrey Hepburn’s all black ensemble in Funny Face. Challenged only maybe by Steve Jobs.

Turtlenecks today come in an excess of different shapes and sizes. They can be wool or cotton, oversized or cropped. When styling a turtleneck, the fashion rule of balance is more important than ever.

Pair a cozy, thick, cable knit turtleneck sweater with a pair of dark skinny jeans or trousers and sleek booties for a classic fall look. Balance a roomy, 90s-style turtleneck with a sexy, even more 90s-style mini pencil skirt. To carry your summer wardrobe over to fall, throw on a turtleneck underneath a slip mini dress or a flowy maxi dress.

For the ultimate winter professional look, layer a tight-fitting sleek turtleneck underneath a blazer. Score bonus points if the blazer is oversized. You can sex up a turtleneck by pairing it with a trim moto jacket, or sex it down by wearing it with a high waisted skirt and dark tights. My personal favorite is the Rachel Green: long-sleeved white turtleneck, plaid mini skirt, knee highs.

And if none of these options spark your fancy, worry not -- you can literally wear a turtleneck with anything and it’ll look good. Pick your favorite sweater or jacket, and think layers; turtlenecks are more versatile than they seem. The common thread between them all is an elongated neck, a protective barrier against the cold winter, and the feeling that you just might be smarter than you thought. So grab your turtlenecks and your smart kid glasses -- we’ve got a long Boston winter of styling ahead of us.

Photography by: Livia Lange