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How to rock the oversized sweater trend this season, according to a stylist

Plus, 11 options to shop that are anything but frumpy!
Writers Cassidy McKenna and Emma Stessman styling oversized sweaters
TODAY Illustration / Courtesy Emma Stessman / Courtesy Cassidy McKenna

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When it comes to our favorite pieces for the colder months, we tend to gravitate toward all things cozy. From fuzzy fleece jackets to soft sweatpants, we want the items that we wear to feel as close to our pajamas as possible — mostly because it makes the idea of getting out of our warm beds to brace the harsh temperatures feel a little less daunting.

But when you need something a little dressier than your favorite sweatshirt, nothing is better than a big, oversized sweater. Thanks to the extra-large fit, it's easy to feel like you're being wrapped in a warm blanket every time you slip one on. And while they're a great choice for days spent lounging at home, they can also be dressed up with a skirt, jeans or nice booties.

"They look absolutely fabulous on every body shape — that's why they keep coming back into style and that's why they're always on-trend," said Cindy Conroy, a stylist and TV personality. And while they're great for the colder seasons, she added that they're a "year-round favorite," making them essential pieces for your wardrobe.

Of course, with oversized options, there's always a risk of looking a little bulky. So, to help you look your best (while still keeping cozy), we asked Conroy to share her tips for styling the fashionable staple.

How to style an oversized sweater

According to Conroy, there are many different ways to style an oversized sweater. For a classic take on the trend, you can style it with a pair of wool trousers (wide-leg pants are in at the moment). "That's one of my faves," she said. She also suggested tucking in the sweater and adding a braided belt. "That mashup of textures is always a winning combo."

If you select a longer option, you can even style it as a dress, Conroy said. "Depending on your mood, you can pair it with a wedge ankle boot for added height, embossed knee-high boots for extra coverage or you can really indulge in that western trend with a cowboy ankle boot," she added. On colder days, when you need a bit more coverage, Conroy suggests styling your oversized sweater with a maxi skirt for "a classic look, that's still very fresh."

And no oversized sweater look is complete without a piece of outerwear, Conroy said. She suggests layering it with a cozy teddy jacket, a relaxed peacoat or an open-front wool coat. "Whatever your pick, the name of the game is mobility," she added. "With so much fabric dancing around, an oversized sweater by default is bulky. Which means you need a relaxed fit to accommodate the extra material. Outerwear selects that have extra room in the armpits and core will be a lifesaver."

How to style an oversized cardigan

When wearing an oversized cardigan, if you're worried about your shape getting lost in the material, Conroy suggests wearing it open with high-waisted pants and a blouse tucked in. "That simple adjustment will define your waistline," she said. Another way to avoid looking too bulky? Add a belt.

"Proportions are everything when it comes to oversized cardigans," she said. "If you're a petite girl like me, size down. You don't want to be swimming in it. You'll still get to wear the trend without looking like the sweater ate you for lunch."

Below, we asked Conroy to share some of her favorite oversized sweaters and cardigans, and we found a handful of top-rated options as well.

Stylist-approved oversized sweaters

Urban Renewal Recycled Spliced Solid Sweater

Conroy said this sweater from Urban Outfitters is "truly a gem." It's made of upcycled materials, so "it's a fashion choice that's good for the planet too," she added.

Zara Jacquard Knit Animal Pattern Sweater

In a season that's typically filled with beiges and other neutral colors, this animal print sweater is a great way to mix up your wardrobe. "It's a cozy yet fierce number that can easily be dressed up or dressed down," Conroy said.

Ted Baker Ccalie Cocoon Oversized Sweater

"If you're going to splurge, the Ted Baker Cocoon Sweater is a must," Conroy said. "The balloon sleeves perfectly bring the drama."

Zara Pocket Knit Cardigan

Conroy also likes this cardigan from Zara. While it has an oversized design, it's slightly cropped to hit right at your waist and still show off your figure.

Zara Oversized Knit Cardigan

"I'm in love with the Zara Oversized Knit Cardigan because it works for both a rustic camping trip and a casual dinner," Conroy said. Not to mention, we think the red color makes it feel like the perfect choice for the holiday season.

Lucky Brand Space Dye Knit Cardigan

Conroy's pick, the Topshop Knitted Edge to Edge Space Dye Cardi in Pink was so popular, it's now out of stock. But we found this similar colorful long-line cardigan that also features a fun, space dye design.

Top-rated oversized cardigans

Anrabess Long Batwing Sleeve Turtleneck

This chic option is currently the No. 1 bestselling Women's Pullover Sweater on Amazon. It comes in more than 30 colors and features stylish details like batwing sleeves and a high-low asymmetric hem.

Old Navy Oversized Voop-Neck Cotton-Stretch Tunic Sweater

This oversized "voop-neck" sweater is sure to become a new staple in your winter wardrobe. It has 240 five-star reviews, and many people say that they love how soft and comfy it is.

Everlane The Oversized Alpaca Crew

According to Everlane, this sweater is a "holiday favorite." It's made from a cozy alpaca material, which the brand says is less prickly, longer-lasting and less likely to pill when compared to other similar fibers.

Athleta Hanover V-Neck Sweater

Multiple colors and sizes of this cute Athleta sweater are already sold out, so you're going to want to get it while you still can. "I love this sweater — it is perfect," wrote one reviewer. "Cozy, fits well, not too hot, I bought in two colors because I love it so much!"

A New Day Women's Button-Front Cardigan

Pair this top-rated cardigan with jeans for a casual look or throw it over a dress for nicer occasions. The piece comes in plus and standard sizes and in four available colors, so there's an option that will suit almost anyone's personal style.

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