25 Stylish Ways To Make The Best-Dressed List In A Turtleneck

Today, turtlenecks are more associated with Apple products than they are with sword fighting. However, during medieval times, these shirts were worn as a protective layer beneath chainmail armor. Even 700 years ago, people took precautions to avoid chafing (via Ssense). By the 19th century, turtlenecks were a wardrobe staple for working-class laborers, acting as a layer of defense against on-the-job injuries.

By the 1950s, starlets like Marilyn Monroe and Jayne Mansfield had popularized the look, and it quickly became a go-to rather than a taboo for stylish women. "At this time, women were taking pants from men; they were taking pant suits and shorts. And they completely co-opted the button down," says Deirdre Clemente, 20th-century American fashion historian. As she explained to The Week, "In the late 1950s so many women across so many different fronts of society pushed the boundaries enough to the point where women in the 1960s could wear a sweater that 50 years before was only worn by a rich man in Harvard."

The worlds of fashion, politics, and protest have always been intertwined. A 2017 Vogue article notes the association between turtlenecks and the Black Panther Party. In 1971, feminists Gloria Steinem and Dorothy Pitman Hughes sported turtlenecks on the cover of Esquire. It wasn't long before Steve Jobs worked to make black turtlenecks the semi-official tech uniform in the 1980s, per NPR. Here's how to style a turtleneck in the 2020s, whether you're coding in Silicon Valley or trying to stay warm during East Coast winters.

Sheer fabrics were on the rise throughout 2022, gaining popularity partially due to the Supreme Court's overturning of Roe v. Wade, according to trend forecaster Jessica Richards (via Marie Claire). If you're new to styling sheer dresses, opt for a solid turtleneck bodysuit underneath to give you a comfortable level of coverage. For starters, check out this seamless turtleneck bodysuit from Kim Kardashian's brand, Skims, and pair it with an Anthropologie sheer tunic dress. Alternatively, pay homage to 14th century turtleneck and chainmail pairings, and check out this mesh gown from Urban Outfitters.

Sure, 1989's "When Harry Met Sally" is remembered for that one diner scene and the age-old question: Can men and women really be friends? But its fashion moments have also earned their rightful place in pop culture canon, specifically Harry and Sally's iconic turtleneck sweaters, per Insider. Like Sally, match your sweater — like this cozy, cable-knit top from Abercrombie & Fitch – with a black mini, tights, and booties. Or, make like Harry and simply pair your knitwear with light-wash jeans and sneakers.

The Beat Generation, spearheaded by writers like Allen Ginsberg and Jack Kerouac, was a 1950s countercultural movement founded on the tenets of sexual liberation, spirituality, and political protest, per Britannica. The term "Beatnik" arose out of the movement. Though it was originally used to negatively stereotype young creatives who fell into Beat Generation tropes, it eventually became a fashion identity. TikToker @th3.crystal.ship edits a montage of Beatnik fits like the classic mini skirt, black turtleneck, and knee-high boots combo, along with the Audrey Hepburn cigarette-pants aesthetic. For more inspiration, look to @sammitery and her use of accessories like berets, belts, and sunglasses.

At first glance, sleeveless turtlenecks sound counterintuitive. "It doesn't make any logical sense but, at the same time, there's something kind of great about how impractical it is," says Vogue's Fashion News Editor Monica Kim. As Market Editor Kirby Marzec advises the site, "Wear the sleeveless turtleneck like you would a t-shirt or undershirt and let it serve as a subtle layering piece." She suggests, "Let it poke out the top of a crewneck sweater or wear with an open blazer. The beauty is that you won't overheat like you would with its long-sleeve sister but you still get that chic neck moment." 

Though turtlenecks were once reserved for fishermen and Navy men, they're now a cubicle must-have for offices everywhere. YouTube's The Lifestyle Cog, Jashan, demonstrates a week of office-ready looks on her channel. For the Wednesday look, the creator matches slim-fitting gray pants with a gray turtleneck sweater and a scarf for a pop of color. Her Thursday fit involves tucking a cable knit turtleneck into a pencil skirt. Pro tip: Jashan recommends using a safety pin to attach your turtleneck to your skirt on the inside to prevent unwanted bunching. Style expert and fashion merchandiser Astar Davidson agrees that turtlenecks are a business-casual necessity. "This is a basic winter staple you'll feel confident wearing with just about everything you own," she tells Reader's Digest. "Tuck it in trouser-style pants for a balanced silhouette, use it as a layering piece, or dress it up with accessories."

Dress up your turtleneck with the simple addition of a necklace. However, as New York-based stylist Lisa von Weise advises Huff Post, "It should not, in any way, fight with the neck." Instead, go for jewelry with a bit more length. "In fact, a pendant or a longer-length necklace would fill in the space and elongate the torso." As several creators, including @lilaclaurels, have pointed out on TikTok, styling a necklace with a black turtleneck is especially tricky. It will always be hard to escape that one picture of The Rock from the '90s (via People). When it comes to knitwear, avoid necklaces altogether and instead accessorize with simple earrings — like these Madewell medium hoops.

The preppy aesthetic is back. Yes, that means the return of vests, per Fashion. TikTok's @cassie.sethna shows off her take on the look, wearing a loose-fitting sweater vest — like this one from English Factory – over a white turtleneck and tailored pants before sliding on loafers. Alternatively, channel the cast of "Gossip Girl" and style your turtleneck-vest combo with a pleated mini skirt and high socks. Finally, embrace the preppy hair renaissance and try your hand at hair ribbons.

Fashion psychologist Shakaila Forbes-Bell points to the "revenge-buying" phenomenon, or, in her words, "shopping to make up for lost time." As she tells Marie Claire, "It's likely that people will use these purchases as a way to explore their individual tastes and creativity, which had been stifled due to the monotony of loungewear choices." If celebrities like Florence Pugh and Rihanna are any indication, part of this so-called "revenge buying" includes a surge in see-through fabrics. Style a sheer turtleneck, like this Free People fit, with your favorite bralette underneath — one you won't mind showing off. Alternatively, go all out in this embellished Amazon top and pair it with pleather pants or a mini skirt for a night out.

The monochrome set — specifically anything bright pink and "Barbiecore" – is one of fashion's current favorites. Etsy trend expert Dayna Isom Johnson calls the style "a much-welcomed mood-booster after the last few years," adding on "Good Morning America" that "'Barbiecore' is all about embracing vibrant hues — particularly the doll's signature hot pink — in everyday life" (via People). Scroll the virtual shelves of Asos to create perfect the look, investing in a bright pink turtleneck and a pink suit set. To pull out all the stops, match the monochrome look with a pair of pink platform shoes.

Thirty years ago, Princess Diana was known for pairing bike shorts with crew-neck college sweatshirts, per Town & Country. Put your own spin on the look by styling bike shorts with an oversized turtleneck sweater. Thanks to a '90s resurgence, bike shorts are trending again. Alternatively, TikTok creator @christelledc wears black bike shorts with a form-fitting cropped turtleneck and a moto jacket, completing the look with a white tote bag and sneakers. When in doubt, you can always turn to Kim Kardashian for style inspiration. In November 2022, she posed on Instagram in a Balenciaga/Adidas athletic turtleneck and bike shorts.

Vogue lists Tom Cruise as an inspiration in turtlenecks, noting his unique combination of black turtleneck and white button down. TikTok's @megmurayama models the aesthetic with a modern twist, layering a short-sleeved button-down shirt over a black turtleneck and pinstriped trousers. The creator accessorizes the fit with silver jewelry and loafers. For the office, pair a neutral-toned turtleneck with a long-sleeved button down and wide-legged trousers. For added dimension, wear a jacket on top –- something like this oversized faux leather blazer from Mango.

You can make your warm weather slip dress work all year round with the help of a turtleneck layer, per Glamour. Simply wear a turtleneck under your go-to summer slip, adding a long trench coat on top for heat. To achieve a cinching effect, @sabsstyle_ on TikTok recommends looping a belt around your waist. Alternatively, take the opposite approach and wear a turtleneck sweater on top of your slip, pairing it with knee-high boots for a cozy fall look. This technique can also be applied to dresses like baby doll minis, a '60s-style shift, or even a tunic.