How to Style Sweaters, According to a Fashion Insider

Summer styling is easy in that all you need to do, really, is abide by a less-is-best mentality: Throw on the easiest and breeziest pieces in your closet, whether that be a billowing sundress or a tee and denim cut-offs, and head out the door. But during the cold-weather season, when keeping cozy is vital and strategic layering gets thrown into the mix, assembling outfits becomes trickier. To save you the stress, we're tackling winter fashion head-on by offering styling insight on the seasonal essential you're likely reaching for the most: sweaters. 

With insight from Liisa Jokinen, founder of the vintage search engine Gem and a street style photographer with a keen eye for fashion, you'll master how to wear sweaters in no time. From lightweight turtlenecks teamed with button-down shirts to chunky winter sweaters tucked into baggy jeans, scroll onward to find eight sweaters outfits you should try in the 2023 season. 

How to Style Sweaters

A Peek-a-Boo Mini

"I would style an oversized sweater with a tiny mini skirt so that the skirt would just peek out a little bit underneath the hem," Jokinen shares with Maire Claire over email, explaining that the trending momentum of the flirty, '60s-era style continues into the winter season. She adds that this combo would pair well with high leather boots but considering she's not a boots person—"at the moment," she stresses!—also consider a "pair of sturdy platform shoes."

Let's Get Knotty

Take a cardigan or knit pullover and tie the sleeves around your shoulders for an outfit hack that exudes editor-off-duty energy without fail. The slung just-so look strikes a perfect balance: yes, you're trying but not trying too hard. It's a fashion-aware look but done with the insouciance of a downtown-bound Mary-Kate Olsen. And now your sweater has become so much more than just a sweater: It's a scarf! It's a security blanket; It's a winter morning spent scrambling and angsting that you have nothing to wear, simplified.

Pull Inspo From a Prepster

"For a more formal outfit," offers Jokinen, "choose a sweater that is not so bulky, a lightweight cashmere sweater, for instance, and layer it with a button-up dress shirt and a blazer. It's a timeless, chic look!" As far as footwear goes, go full-tilt prep school dropout with a pair of chunky leather loafers and visible socks.

Knits on Knits

Go double duty on sweater weather with a coordinating knit set. In addition to being a dually cozy ensemble, the knit-on-knit combination delivers a polished impact with little sartorial brain power required on your part. In other words, this is a sweater outfit ideal for lazy dressers who want a put-together persona but don't have the capacity to spearhead wholly original looks themselves.

Strategic Layering

"I love layering sheer or thin turtlenecks underneath a sweater. Nothing too thick or bulky, though," cautions the street style expert, "because you don't want to look and feel like a snowman in your layers!" Team your layered sweaters with a skirt suit for a modernized yet retro-reminiscent look for in-office work days when you're in charge of leading the morning meeting.

It's Electric!

Amongst all the possible sweater outfits, Jokinen's personal favorite is her "neon green 15-year-old Acne Studios sweater with my secondhand painted Eckhaus Latta jeans." Yield a similar head-turning effect by pairing an electric lime sweater with worn-in denim trousers or, for a more dressed-up take, a printed slip skirt.

To the Max

As for styling a sleek turtleneck, Jokinen says, without question, her go-to option is "a maxi denim skirt!" Not only is the long silhouette trending at the moment, but the vintage fashion expert says it's "a fun alternative to regular blue jeans that can be nice and warm during the winter months." 

A Tucked-In 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 need to do is work on the art of the tuck—grab just a handful of your hem and slip it into the waistband—and you're golden. For a finishing touch, tuck your hair into the turtle, too, à la Phoebe Philo-era Céline. 

Meet the Expert

Liisa Jokinen

Liisa Jokinen is the founder of the Gem vintage search app and a street style photographer based in New York.  After moving from Helsinki, Finland to New York in 2017, she first launched NYC Vintage Map to discover all the best vintage and thrifting spots in the city. Besides old clothes, she is passionate about running, swimming in cold water, and all things floral.