Summer styling is easy because all you have to do is stick to the less-is-more mentality: throw on the lightest, breezy pieces in your wardrobe, whether it’s a high-waisted sundress or a cropped denim top. , and exit through the door. But during the cold weather season, when staying comfortable is key and strategic layering is thrown into the mix, putting together an outfit becomes more difficult. To save you the stress, we tackle winter fashion head-on by offering you styling insight on the seasonal essentials you’re probably reaching for the most: sweaters.
With the insight of Liisa Jokinen, founder of vintage search engine Gem and street style photographer with a keen eye for fashion, you’ll know how to wear sweaters in no time. From lightweight turtlenecks paired with button-down shirts to chunky winter sweaters tucked into baggy jeans, scroll on for eight sweater outfits you should try in 2023.
How to style sweaters
Peek-a-Boo Mini
“I would style an oversized sweater with a little mini skirt so that the skirt peeks out just a little bit under the hem,” Jokinen shares with Maire Claire via email, explaining that the flirty ’60s style trend continues into the winter season. She adds that this combo would pair well with tall leather boots, but since she’s not a boot person—”right now,” she stresses!—also consider “a pair of sturdy platform shoes.”
Ader Error Oversized sweater in marl knit
GANNI Wool blend mini skirt
Sam Edelman Drina Riding Boot
Let’s Get Knotty
Grab a cardigan or knit sweater and tie the sleeves around your shoulders for a hack outfit that unmistakably exudes the energy of an off-duty editor. The self-contained look strikes the perfect balance: yes, you try, but you don’t also heavy. It’s a fashion-conscious look, but done with the insouciance of Mary-Kate Olsen going downtown. And now your sweater has become much more than a sweater: it’s a scarf! It is a security blanket; It’s a winter morning spent twitching and fretting about having nothing to wear, simplified.
COS pure cashmere sweater
Pangaia PPRMINT™ Organic Cotton T-Shirt Core
Intermix Heidi wide twill pants
Get Inspo from the Prepster
“For a more formal outfit,” Jokinen offers, “pick a sweater that’s not too bulky, like a lightweight cashmere sweater, and layer it with a button-down shirt and blazer. It’s a timeless, chic look!” As for footwear, go all-out prep school with a pair of chunky leather loafers and see-through socks.
Vince Essential Long Sleeve Turtleneck
H&M cotton shirt
Boden woolen jacket in drawn wool
Knitting on knitting
Go double duty in sweater weather with a coordinating knit set. In addition to being a doubly comfortable kit, the knit-on-knit combination gives a refined feel with little tailoring skill required on your part. In other words, this is a dressy sweater ideal for lazy dressers who want a polished persona but don’t have the capacity to pull off a completely original look themselves.
A delicate set of a knitted sweater and cashmere skirt
Everlane Pure Silk Relaxed Fit Shirt
Cole Haan Bridge MaryJane Ballet
Strategic stratification
“I love layering sheer or thin turtlenecks under sweaters. Nothing too thick or bulky,” warns the street style expert, “because you don’t want to look and feel like a snowman in your layers!” Pair your layered sweaters with a skirt suit for a modernized yet retro look for workdays at the office when you’re in charge of running the morning meeting.
Commando Chic mesh turtleneck with long sleeves
11 Honoré Kiara V-neck wool-blend pullover
Nº21 Fully pleated mini skirt
It’s electric!
Among all possible sweaters, Jokinen’s personal favorite is her “15-year-old neon green Acne Studios sweater with my second-hand painted Eckhaus Latta jeans.” Achieve a similar head-turning effect by pairing a taupe sweater with distressed denim or, for a dressier look, a floral print slip skirt.
H&M oversized sweater
La DoubleJ layered skirt
Vagabond Alina high boots
For Max
When it comes to styling a chic turtleneck, Jokinen says, without a doubt, her go-to is a “denim maxi skirt!” Not only is the long silhouette on trend right now, but a vintage fashion expert says it’s “a fun alternative to regular blue jeans that can be nice and warm during the winter months.”
Banana Republic Mitico Crew Neck Sweater
Raey Split Back Organic Cotton Maxi Denim Skirt
Vince Camuto Salsuh boot
A snuggled turtle
Here’s where you can rely on your basic blue jeans: when styling any of the many chunky turtlenecks you have in your cozy rotation. All you have to do is work on the art of underlining—just grab a handful of hem and tuck it into your waistband—and you’re golden. For the finishing touch, tuck your hair into a turtleneck too, à la Phoebe Philo-era Céline.
Some navy blue turtleneck with counter details
Still here Childhood in classic blue
Rag & Co Margen boots