The slouchier, the better seems to be the sartorial motto these days, which makes learning how to style an oversized sweater well worth your while. After all, roomy knits are the backbone of any strong winter wardrobe. And cozy, baggy sweaters abound at all your favorite retailers, from Fair Isle prints to cable-knit silhouettes. So why not join in on all the fun and work the cold-weather essential into your everyday style?
The beauty of an oversized sweater lies in its versatility, as it can be paired with virtually any bottom hanging in your closet. But here’s our best fashion tip to help get your styling juices flowing: Consider the overall vibe you want to achieve with your oversized sweater look. For an effortless, cool-girl-approved outfit, for example, you can pair the knit with slouchy jeans à la Hailey Bieber. Believe it or not, the separates work together in perfect harmony. On the other side of the spectrum, balancing proportions creates an elevated, put-together ensemble. Tailored trousers will get the job done for this kind of look, as will a body-hugging miniskirt.
For more guidance on pulling off an oversized sweater with aplomb, we’ve compiled five fashion-forward outfit ideas to re-create below. Leave no sartorial stone unturned this season.
As a dress
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No pants, no problem. With a billowy knit sweater, you have the option to leave your bottoms at home. Simply marry the short silhouette with over-the-knee boots for a balanced look. As far as styling goes, consider layering tights underneath for extra coverage or show a bit of leg sans hosiery. Either way, this two-piece sweater outfit formula packs a bold punch.
Madewell Sweater Minidress
Jeffrey Campbell Parisah Over-the-Knee Boots
Vanlinker Retro Aviator Sunglasses
Mejuri Puffy Charlotte Ring
With fitted denim
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If you’re worried about looking like you’re, well, drowning in a big sweater, here’s an easy styling tip: Keep things sleek on the bottom. In other words, skip baggy denim in favor of straight-leg or skinny jeans. For a look that’ll likely fly in the office, try layering an oversized pullover atop a crisp white button-down—bonus points if you leave one collar hidden underneath the knit—or a turtleneck version. Polished heels play well with the casual look’s sophisticated feel.
Nordstrom Oversized Cashmere Turtleneck Sweater
Madewell Pencil Jeans
Jenny Bird Lennon Hoop Earrings
Zara Leather Heels
With baggy pants
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Proof that, yes, you can style oversized sweaters with equally spacious wide-leg pants. As mentioned, the fashion crowd has been making a strong argument for head-to-toe slouchy silhouettes, and we’re totally here for it. It doesn’t hurt to sprinkle in some polished accents into the look, such as small oval-shaped sunglasses and leather ballet flats or kitten heels. Resist the urge to tuck in your chunky knit with this look, and don’t be surprised if you’re mistaken for a model off-duty as you’re running errands.
Khaite Mae Sweater
Veronica Beard Robinne Wide-Leg Pants
Le Specs Duskfall Sunglasses
Malone Souliers Emmanuelle 45 Pumps
With sophisticated basics
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Sticking to wardrobe classics is always a sound approach, especially when still figuring out how to style an oversized sweater. For instance, a chunky sweater with extra-long sleeves and baggy trousers makes for a chic, unfussy mash-up. Follow this less-is-more philosophy with your accessories to create a polished look. Might we suggest a pared-back leather handbag and sleek boots?
COS Cashmere Funnel-Neck Sweater
Abercrombie & Fitch Sloane Pants
Coach Laurel Shoulder Bag
Vegabond Nella Boots
With a shirt tied around your waist
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A styling technique that always makes an outfit 10 times more interesting? Tying a button-down around your cozy sweater. In the street style look above, the hack provides a cinched-in look with an oversized cable-knit (think of the top as a makeshift belt). Add edge to the slightly preppy getup by way of buckle-heavy moto boots and a cool-girl lipstick. For bottoms, you can wear the sweater as a dress with this look, too, or add a fitted miniskirt or midiskirt for another layer. Leggings or tights underneath are an option for additional warmth.

