How to style oversized sweaters for maximum wear and comfort this winter

In need of some help with how to style oversized sweaters like a fashion pro? You've come to the right place

A composite of street style influencers showing how to style oversized sweaters
(Image credit: Getty)

Mastering how to style oversized sweaters will help you glide through winter, effortlessly. Chic and oh-so-cozy, the oversized sweater look is one of the most coveted this season, but as it plays with enlarged proportions, there are a few simple tricks to stop the style from becoming overwhelming.

A welcome addition to our winter wardrobe, oversized sweaters have an instantly snuggly and relaxed aesthetic. No longer just reserved for lazy Sundays, when it comes to how to style oversized sweaters, this practical look will work with anything from workwear to jeans. Whether you opt for chunky cable knits or voluminous pullovers, the key to grasping how to style oversized sweaters all comes down to finding the perfect silhouette. The best sweaters for this style are designed to be oversized rather than just sized up as the best-oversized sweaters are roomy in all the right places, without swamping your silhouette. 

A handy layering tool, you can wear a lightweight oversized sweater under the best wool coats during the winter or simply on its own in place of the best winter coats on warmer days. Play with proportions and team with wide-leg trousers for a fashion-forward look or throw on over dresses, adding chunky boots for a rebellious edge.

How to style oversized sweaters - outfit inspo from the experts

When it comes to how to style oversized sweaters, it's all about balancing your proportions and making sure you're wearing the sweater, rather than the other way around. You always want to ensure you've highlighted your frame in some way, whether that's a nipped-in waist, a hemline that shows off your pins, or an off-the-shoulder design, to ensure there is a good balance between you and your knit. With a plethora of outfit opportunities available, we’ve rounded up our favorite looks from the style set that you can start weaving into your everyday wardrobe pronto.

1. How to style oversized sweaters with leggings

A composite of street style influencers showing how to style oversized sweaters with leggings

(Image credit: Getty)

Thanks to its voluminous silhouette, an oversized sweater looks great teamed with more figure-hugging styles such as the best leggings, as they aid in balancing proportions. Here you can really go big with your sweater - think the bright hues of dopamine dressing, chunky roll necks and cable knit textures. Make the sweater the star of the show by pairing it with wardrobe essentials - a simple pair of black leggings will do the trick or you can add some texture with some leather leggings for a smarter spin.

2. How to style oversized sweaters with jeans

A composite of street style influencers showing how to style oversized sweaters with jeans

(Image credit: Getty)

Learning how to style an oversized sweater with jeans is a must. A combo you can reach for time and time again, it offers a cool, off-duty style. Lean into that laid-back aesthetic and opt for relaxed fits on your jeans such as straight-leg, mom jeans and boyfriend styles. Any sweater will work with this look but for extra style kudos, we recommend opting for ribbed textures, fringe detailing, and cable knits for a delightfully cozy, yet directional feel. Team with trainers or smarten up with a pair of heels to render it date-night-ready. To ensure this look still highlights your silhouette, opt for jeans with ankle-skimming hemlines, rather than floor sweeping denim.

3. How to style oversized sweaters with boots

A composite of street style influencers showing how to style oversized sweaters with boots

(Image credit: Getty)

When it comes to a winter power pairing, you can’t beat an oversized sweater and the best winter boots. Whether you go for one of this season's boot trends, such as a glamorous over-the-knee style or a forever on-trend, cute little ankle boot, oversized sweaters work with any boot thrown at it. 

If your oversized sweater is veering towards the jumper dress territory, try pairing with a taller boot such as this season's best knee high boots and opaque tights, or an over-the-knee pair for extra leg coverage. Classic shades such as tan and black will give you more versatility and showcase how to style oversized sweaters to perfection.

4. How to style oversized sweaters over a dress

A composite of street style influencers showing how to style oversized sweaters with a dress

(Image credit: Getty)

If you're wondering how to style oversized sweaters for a more dressed up occasion, you can definitely make this snuggly look work for party season. If you need a great idea for what to wear on Christmas day, make your fancy frocks work overtime by layering an oversized sweater on top for a smart casual outfit idea that is effortlessly chic. 

For an added dose of romantic drama, look to feminine tiered skirts with ruffled detailing. Quite a statement-making look, keep it wearable and stick to tonal shades of creams, grays and browns rather than bold color. If your figure is feeling swamped, layer a belt or a belt bag on top to define your waist.

5. How to style oversized sweaters with skirt

A composite of street style influencers showing how to style ovesized sweaters with a skirt

(Image credit: Getty)

Much like wearing an oversized sweater with a dress, the skirt-sweater combo is an easy and elegant look to pull off. Avoid tucking your whole jumper into the skirt as this can look bulky and instead, try the half-tuck - just tucking in the front - to add structure and highlight your waist, but without sacrificing on that relaxed look. Create a coveted high-low aesthetic and keep your sweater slouchy and your skirt polished. Look for luxe textures such as satin, silk and leather and finish with a pair of the best designer heels. Brunch outfit idea - sorted.

6. How to style oversized sweaters with wide leg trousers

A composite of street style influencers showing how to style oversized sweaters with wide leg trousers

(Image credit: Getty)

Consider this look the comfiest of the bunch and one we’ll be embracing this winter. Nailing how to style oversized sweaters with a pair of wide-leg pants is the perfect formula for how to dress simple but stylish. To stay in the smart lane, layer the knit over a collared shirt and finish with a pair of the best loafers or mules. You can try the half-tuck here to add structure and keep it fluid by sticking to one color or a mono palette.   

Charlie is the Deputy Fashion Editor at Future plc across multiple women’s magazines including Woman & Home, Woman and Woman's Own.


She bagged her first magazine job in 2009 and has previously written for titles including Stylist, Closer and Dare. Over the years Charlie has embraced anything that was thrown at her from styling celebrities to testing out the best jeans on the high street to writing about must-have beauty buys.


With a weakness for a printed midi dress, Charlie is on a mission to shop more sustainably and loves finding new ethical brands and second-hand buys.