9 Chic Ways to Style Grey Knitwear for Winter 2026, According to the Street Style Scene

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We just want to stand up and say: gray knitwear is high Underrated. Season after season, what are often considered “basics” have indeed made their way into fashion’s most fashionable circles, from Fashion Editor to model off duty. It’s easy to see why: Gray sweaters are versatile and available in a variety of shades and silhouettes—from a loose V-neck to a classic crewneck to a chic cardigan—gray sweaters can elevate even the simplest of uniforms. Who can say no to a dose of chic, extra coverage?

fashion magazine Gray Knitwear Ultimate:

Kendall Jenner is a famous gray sweater devotee. While out for dinner with the power duo in Los Angeles early last fall, she stepped out in a gray cashmere crewneck sweater (from The Row, of course). She wore a low-key knit sweater hung loosely over a crisp white T-shirt, pleated black trousers and distressed ballet flats. The result is minimal yet undeniably cool, proving that chic often lies in the simplest acts of layering.

fashion magazine Executive fashion director Lisa Aiken provides another point of reference. Her designs were more sophisticated: a roomy gray turtleneck paired with a flared A-line skirt, finished with a cozy cashmere scarf for a modern ladylike look. (Bonus points if you add a pair of pointed-toe Prada pumps, as Aiken did.)

Here’s proof that sometimes it’s best to go back to basics. Shop nine street-style-approved ways to rock a timeless fashion favorite: the gray knit.

Kendall Jenner and MaryKate Olsen spotted after low-key dinner at Sushi Park

Photo: Backgrid

Celebrities’ top choice

Who better to draw inspiration from for wardrobe essentials than supermodel Kendall Jenner? Wear it casually with a gray crew neck sweater, a casual white T-shirt, pleated black trousers and simple ballet flats to highlight her casual cool style. The extra layer adds subtle dimension while providing chic coverage. Finish it off with a stylish leather tote and a pair of black sunglasses for a look that’s totally Jenner-approved.

Kate

x Oliver Peoples 1983C sunglasses

9 Chic Ways to Style Gray Knitwear for Winter 2026 Based on the Street Style Scene

Photography: Phil Oh

Beautiful gray finds

We’re not just talking about chunky knits. The lightweight, slim-gauge styles are just as (if not more) stylish. Milanese editor Marta Oldrini proved this, pairing a Cos knitwear with a matching gray midi skirt, an edgy leather biker jacket and a slim turtleneck. Featuring a crocodile-embellished handbag and long pendant necklace.

Coase

Seamless long sleeve top

Noor Hamour

Beck oversized leather jacket

Chloe

medal pendant necklace

9 Chic Ways to Style Gray Knitwear for Winter 2026 Based on the Street Style Scene

Photography: Phil Oh

Striped Polo Shirt

It’s hard to ignore the impact striped rugby shirts have had on fashion right now, from the runways to the editors wearing striped rugby shirts. Even classic gray knitwear gets a sporty treatment. As seen in this sophisticated Parisian style, Éterne’s striped knitwear is paired with casual blue jeans, a denim work jacket and stylish Adidas sneakers. Accessories by Khaite and Lié Studio elevated the look to front-row status.

Image may contain Phil Kaufman clothing, outerwear, accessories, bags, totes, adults, coats, watches and shoes

Photography: Phil Oh

Thick V-neck

With New York Fashion Week right around the corner, we can almost guarantee that Lisa Aiken will be wearing some version of this stylish uniform. According to her lookbook, she started by layering a chunky V-neck sweater from &Daughter over a gray knit midi skirt and finished with a fringed cashmere scarf. Top priority? Prada’s pointy-toe pumps—seemed to be on every editor’s wish list last season. Of course, her signature Ray-Ban sunglasses are also a must-buy.

Image may contain Myrra Malmberg clothing coat scarf people coat blonde and hair

Photo: Thomas Razzano

Sweater as scarf

Wearing a sweater as a scarf was a popular street style trick last season and it’s still going strong right now. This look was spotted during Copenhagen Fashion Week and offers an ultra-chic on-trend look. Pair Everlane’s oversized crewneck sweater with Arma’s suede trench coat and Gap’s chocolate brown trousers, then pair it with high-heeled boots and a robin’s egg blue bag to create a fresh pop of color.

Image may contain Natsuo Marisol Espinoza Svein Berge Gülhan Şen Mariano Rajoy adult head and face

Photography: Acielle/Style Du Monde

Soft V

Just last week during the Milan menswear show, the stylish showgoer added a sexy edge to a soft gray V-neck sweater by revealing a hint of red underneath. Complete the runway look with a sheer skirt, Prada lime satin drawstring bag and taupe pumps.

Gucci

crystal logo slingbacks

9 Chic Ways to Style Gray Knitwear for Winter 2026 Based on the Street Style Scene

Photography: Phil Oh

roomy wool

Quality wool knitwear can be as luxurious as cashmere. Take the street stylist’s baggy gray crewneck sweater, for example: its oversized silhouette pairs perfectly with a pleated midi skirt, knee-high boots and a small black croc-embossed belt. Make the look your own, below.

9 Chic Ways to Style Gray Knitwear for Winter 2026 Based on the Street Style Scene

Photography: Phil Oh

Polished Polo Shirt

Choose a preppy polo style to add a touch of sparkle to your gray knitwear. Vanity Fair’s Nicole Chapoteau is a fan of boyish looks, and she looked glamorous outside last season’s Miu Miu show in the label’s bold yellow leather skirt, camel blazer and black penny loafers, which she paired with matching gray socks.

madewell

reversible cardigan blazer

9 Chic Ways to Style Gray Knitwear for Winter 2026 Based on the Street Style Scene

Photography: Phil Oh

classic cardigan

When it comes to wardrobe staples, there’s nothing like the tailored gray cardigan—it’s even become a mainstay on Miuccia Prada’s runways. British fashion magazine Chioma Nnadi clearly agrees, pairing her double-layered shirt with casual blue jeans and playful loafers. This pair from J.Crew is particularly good.

Jay Crew

The perfect cashmere cardigan

Jamie Haller

Zebra-print calf hair loafers

Everland

cashmere short cardigan

rice

Brooklyn turtleneck sweater

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