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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
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.
RRP: $98 / £89 | Once you try a pair of Spanx faux leather leggings, you’ll never look back. These feature a Power Waistband for core compression and a great contouring finish, while the faux leather fabric lifts and shapes for a flattering fit.
RRP: $1,420 / £1,120 | Sometimes only the best cashmere sweater will do and we love the bold hues used here. Crafted from 100% cashmere, it’s unapologetically indulgent, featuring a classic crew neck and dropped shoulders for a relaxed fit.
RRP: $125 / £95 | Every closet needs a pair of the best white trainers and the chunky platform sole gives these a retro edge. Guaranteed to go with everything, they feature the signature crocodile logo and a simple lace-up design for superb versatility.
2. How to style oversized sweaters with jeans
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.
RRP: $319 / £159 | The fringe detailing gives this chunky sweater a playful and on-trend finish. Crafted from a responsibly sourced cotton blend, it has a relaxed fit and cable knit detailing on the collar bone. Available in bold red, blue and brown.
RRP: $148 / £178 | Need a denim trends update? Head to Reformation for jeans that are stylish and sustainable. These sit high on the waist for a midriff-flattering finish and have a relaxed straight leg to balance hips. The perfect everyday style.
RRP: $228 / £255 | These feathery mules are your fast-track way to elevating the simplest of looks. They tick all the boxes with a contemporary square toe, a luxe satin finish and a fun feather trim for a party-ready feel, all in a versatile black hue.
3. How to style oversized sweaters with boots
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.
RRP: $139 / £110 | This longline oversized sweater can be layered over trousers or worn alone with tights and boots for a glamorous, yet cozy look. The sweet pink hue taps into one of the top winter 2022 fashion trends, that you can wear into spring too.
RRP: $270 / £195 | The perfect evening boot, these knee-high boots are the ideal companion to your oversized knits. Crafted from premium leather, the taupe hue is wearable and timeless and there’s a handy zip on the side ensuring they'll go on with ease.
RRP: $675 / £368 | Make any outfit look instantly more expensive with an elegant cream coat. This has a waist-defining self-tie belt for a feminine silhouette and it's made from a super soft wool blend that’ll keep you toasty and glamorous all winter.
4. How to style oversized sweaters over a dress
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.
RRP: $589 / £375 | When it comes to dreamy statement gowns, Needle & Thread is our one-stop shop. Featuring a pretty floral design, tulle ruffles and floaty sleeves, it oozes romance. Available in three lengths this can be worn for weddings too.
RRP: $59.99 / £35.99 | You can never have too many gray sweaters in your arsenal and we’ll be living in this all winter long. A thick knitted wool-mix fabric with a cozy turtleneck, it’s your go-to for keeping warm and chic as temperatures plummet.
RRP: $159 / £99 | We love a buy that works overtime and this belt-bag combo does just that. The pouch is removable giving extra versatility, so it can be worn just as a belt, or leave your clutch at home and add the metallic belt bag for a party-ready finish.
5. How to style oversized sweaters with skirt
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.
RRP: £175 / £177 | Everlane is a pro at elevated basics and this turtleneck is no exception. The sunny yellow hue will lift your look and the alpaca blend is gorgeously soft. With an extra voluminous turtleneck it has that cozy cocoon factor nailed.
RRP: $425 / £250 | A leather pencil skirt will add a cool twist to your workwear wardrobe. This has a front slit for easy movement and sits high on the waist to help sculpt and define your shape. Team with oversized knits and silky blouses.
RRP: $775 / £595 | You can always rely on a pair of classic leopard print pumps to see you through any wardrobe crisis. A neutral print, they go with everything and are perfect for adding personality to your look, while keeping you on-trend too, winner.
6. How to style oversized sweaters with wide leg trousers
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.
RRP: $350 / £225 | Keep it simple in a cool cream sweater, guaranteed to get plenty of outings. For an added dose of luxury, this knit is crafted from 100% cashmere which will ensure your body temperature is perfectly regulated this winter.
RRP: $180 / £99 | Tap into that relaxed tailoring trend with these chic plaid pants. The side stripe gives them a sporty spin, while the wide-leg cut will help elongate your pins. Pull the look together and finish with the best blazer for instant, added polish.
RRP: $215 / £135 | A modern twist on the classic white shirt, this shirt features elegant, deep cuffs and super soft cotton with a slight sheen for added character. Easy to tuck in or leave loose, it’s a stylish building block to any over '50s capsule wardrobe.
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.
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