25 Oversized Sweaters for Chic Winter Style

By Kaia Saunders / January 27, 2017
Blonde woman in white track pants and an oversized beige mohair sweater

Who doesn’t love to wrap up in layers of warm, cozy fabrics during winter? That makes an oversized sweater the perfect choice for both keeping warm and looking chic this season.

Comfortable, versatile and classy, an oversized sweater is the one item you’ll find yourself choosing again and again. Think luscious fabrics like lamb’s wool, mohair, cashmere and brushed cotton. Then there are the necklines – turtleneck, cowl neck, crewneck and off-the-shoulder, to name just a few.

Whatever your style preference, there’s an oversized look for you. Edgy and modern? There’s nothing as cool as an oversized sweater and ripped jeans. Sporty and tomboyish? How about an oversized sweater, skinny jeans, and sneakers? Feminine and girly? Try an oversized sweater dress with knee-high boots.

With so many styling options out there, we’ve compiled 25 of the best oversized sweater outfits to get you well on your stylish way.

Winter’s Edge – Get The Edgy Look In An Oversized Sweater

1) Lessons in Layering

Trendy woman in an oversized grey sweater and black leather leggings

Shiny black leather complements an oversized sweater to edgy perfection (photo: rosewe.com)

The great part about winter dressing is that truly anything goes when it comes to layering styles and fabrics. This outfit consists of individual items cleverly pieced together into one eclectic look. Shiny black leather leggings are worn underneath a long oversized grey turtleneck sweater, with a white cotton T-shirt peeking out beneath. A quirky addition to the look is a pair of white Converse sneakers plus a dainty black clutch purse.

2) Dove Grey Days

Chic woman in black ripped jeans and a grey oversized sweater

Layers of dove grey soften the harsh effect of ripped skinny jeans (photo: notjessfashion.com)

Light dove grey is one of winter’s most elegant, sophisticated shades. Yet, when this gentle color is combined with darker items, the effect is suddenly urban, modern and ultra-trendy. Here, an oversized ribbed woolen sweater peeks out beneath a voluminous grey pashmina wrap scarf. Completing the edgy ensemble is a pair of black ripped skinny jeans and pointy-toed black leather ankle boots. Remember to accessorize suitably too, as seen here with mirror aviator sunglasses and a dainty black leather sling handbag.

3) Moody Blues

Blonde woman in an oversized navy blue sweater and ripped jeans

An outfit of dark denim and charcoal creates a moody wintry aesthetic (photo: happilygrey.com)

Winter is the perfect time to get a little moody and edgy with your wardrobe. This dark-toned ensemble showcases the best of the chilly winter aesthetic in varying shades of dark grey, navy blue, and black. An oversized sweater made of loosely ribbed navy blue wool is beautifully set against ripped dark blue skinny jeans. Tying it all together seamlessly is a pair of dark grey ankle boots and a black tote handbag.

4) Neon Notions

Stylish woman in black leather pants and an oversized black woolen sweater

A bright neon handbag adds fun and whimsy to an all-black winter ensemble (photo: louwhatwear.com)

Color is the easiest way to brighten up a monochrome outfit of all-black clothing, especially during overcast, miserable weather. Here, the iconic Hermès Birkin handbag in luminous neon yellow adds fun and folly to a grey wintry day. An oversized black sweater is seen peeking out underneath a charcoal-colored duffel coat and extra-long pashmina wrap scarf. Leather leggings keep things edgy and cool, topped off with platform suede ankle boots.

5) Hipster Style

Blonde woman in skinny jeans and a navy blue oversized sweater

It’s hipster style all the way in layers of navy blue, black and grey (photo: weworewhat.com)

We love this trendy take on the classic all-navy look. Embrace the urban hipster look by combining an oversized woolen sweater in deep navy blue with matching stonewashed dark blue skinny jeans. Black patent leather boots keep things chic while a grey beanie and black round Ray Ban sunglasses add that modern streetwise factor.

6) Mustard Muse

Brunette woman in an oversized mustard sweater and black ripped jeans

Add some earthy flair to your ripped jeans with a rich mustard sweater (photo: afashionlines.tumblr.com)

There’s nothing like a bold, rich color to make a style statement and this mustard oversized sweater sure makes a splash. The loose woolen fabric is casually tucked into black skinny jeans ripped roughly along the thighs. The solid black color then leads down into black suede ankle boots. To accessorize the overall look, we find a large black leather tote bag and a fashion-forward black wide-brimmed hat.

7) Easy Style

Sporty woman in black denim, white sneakers and an oversized grey sweater

It’s all about comfort in this outfit of oversized wool, fitted denim and trainers (photo: howtochic.blogspot.co.za)

Spruce up those trusty skinny jeans this season with the simple additional of an oversized woolen sweater. The loose, comfortable fabric is the ideal pairing to go with slim-fitting black skinnies ripped right on the knee. Top off the laidback, urban ensemble with your favorite pair of white sneakers and you’re all set for a day of easy-going exploring.

Nude ‘N Neutral Sweaters For A Stylish Winter

8) Beanie Beauty

Blonde woman in white track pants and an oversized beige mohair sweater

White track pants are quirky and chic when paired with an oversized mohair sweater (photo: leneorvik.no)

White will always be a winner come wintertime and with good reason – crisp, clean and sophisticated, white clothing is timeless. In this outfit, however, we see something different. Instead of the usual white skinny jeans, this ensemble teams a pair of fitted white track pants with an oversized mohair sweater in elegant beige. Matching beige snow boots complete the look along with a dark grey beanie for an unexpected twist.

9) Shoulder Savvy

Brunette in cream oversized sweater and dark blue skinny jeans and floppy hat

When it comes to an oversized sweater, the wider the collar, the better (photo: andeelayne.com)

An unexpected pop of skin is a fun way to play with fashion on those not-so-chilly days, and an oversized sweater is your perfect excuse to do so. This large cream woolen sweater is worn casually with dark blue skinny jeans and a trendy brown floppy wide-brimmed hat. A further quirky touch comes in the form of a patterned sling hand bag with colors in a matching color palette.

10) Shades of Beige

Elegant woman in a beige oversized sweater and beige over-the-knee boots

The beauty of beige shines through in this ensemble of layered separates (photo: thedarlingdetail.com)

Layers upon layers of nude-colored fabrics have an elegant, timeless appeal – perfect for stylish winter dressing. This outfit combines basic black leggings with an oversized beige sweater worn under a large plaid pashmina scarf. Over-the-knee beige boots polish off the look along with a stylish beige sling handbag.

11) Blushing Beauty

Classy woman in a beige oversized sweater and blue skinny jeans

Blush pink and nude make this oversized ensemble a style must (photo: theclosetfromhell.com)

Here’s a clever little style tweak that’s both cute and bang on trend. When wearing an oversized, voluminous sweater, pair it with ankle-grazing jeans and simple, slip-on moccasins. The small sliver of skin down on the foot is unexpected and ever-so chic, especially when your chosen footwear matches your skin tone as well as the overall coloring of your clothing. A large faux-fur clutch purse in blush pink beautifully ties this ensemble together.

Get Layered In Luxurious Fabrics

12) Sporty Luxe

Sporty woman in grey skinny jeans and an oversized grey mohair sweater

Get your sporty vibe on with white sneakers and an oversized mohair woolen sweater (photo: thefashioncuisine.com)

Here’s a nod to the streetwise athleisure trend so popular among bloggers and designers alike. It’s one of the most effortless yet contemporary ways to style yourself during the chilly months. Here we see distressed grey skinny jeans worn easily under a matching grey oversized sweater made of brushed mohair wool. Completing the sporty urban look, are bright white sneakers and minimal gold jewelry.

13) Slim Silhouette

Stylish brunette in blue skinny jeans and a grey oversized sweater

Slim jeans plus an oversized sweater create a sexy feminine shape (photo: notyourstandard.com)

Just because you’re wearing an oversized sweater doesn’t mean you can’t still show off your figure. Pair a larger-than-usual top with form-fitting skintight jeans like these to create sexy curves and add dimension to your body. The ankle-skimming hemline also further slims the legs before leading down to sexy, eye-catching statement heels. Polish off the look with your favorite accessories, like this grey satchel and subtle metallic jewelry.

14) Draped Diva

Elegant brunette in dark blue jeans and a beige oversized sweater

Create a unique look with a large, oversized sweater and slim-fitting jeans (photo: demode.me)

Oversized and comfy needn’t mean frumpy and boring. Take this layered, multi-dimensional ensemble. This woolen sweater has a roomy, voluminous shape which, when worn with slim jeans, creates an interesting, unexpected shape. The effect is stylish, eclectic and unique. Complete the ensemble with brown lace-up leather boots and a matching brown carry-all handbag.

15) Cut-out Chic

Blonde woman in a blush pink oversized sweater and blue skinny jeans

An oversized sweater in soft brushed wool is both classy and comfy this winter (photo: maxlera.ru)

For lazy days that call for a little extra warmth and comfort, you can’t go wrong with an oversized sweater in the softest, most luxurious fabric you can find. This blush-colored number consists of finely ribbed wool with a slightly raised crewneck and slouchy longer-length sleeves. The perfect accompaniment is a pair of skinny jeans in dark blue plus a men-style watch in matching navy blue.

16) Rock Star Uniform

Trendy woman in a grey oversized woolen sweater and ripped boyfriend jeans

Bring out your inner rock ‘n roll wild child with an oversized off-the-shoulder sweater (photo: instagram.com)

Think 90s rock ‘n roll and channel your inner Kurt Cobain with this edgy street style. Get the look by opting for a pair of high-waisted boyfriend jeans roughly ripped at the knees. What really makes the outfit pop though is an oversized grey woolen sweater left to drape casually off the shoulders and tucked loosely into the waistband of the jeans. A black leather sling handbag with silver buckle detailing adds to the devil-may-care rock persona.

17) Winter Palette

Classy brunette in grey skinny jeans, a black coat and an oversized sweater

The dark colors of winter combine into one classy yet modern ensemble (photo: dressmix.com)

This look screams class all the way. In varying shades of grey, charcoal, navy blue and black, you’ve got the colors of winter combined into one stylish ensemble. An oversized grey turtleneck woolen sweater is warm and roomy on top while grey skinny jeans are sleek and slimming down below. A long navy blue coat pulls it all together stylishly, topped off with black leather ankle boots and a black sling handbag.

Light and Soft Layered Sweaters

18) Casually Chic

Stylish brunette in blue skinny jeans and cream off-the-shoulder sweater

Luxurious oversized fabrics add easy glamour to classic blue jeans (photo: instagram.com)

The simplest clothing combinations make for the classiest outfits. Case in point: these skintight stonewashed blue skinny jeans worn casually with an oversized cream woolen sweater. Whether you’ll be spending the day sifting through a street market or just lounging about on the couch, this laidback ensemble is both comfortable and cute. Accessorize with delicate gold jewelry for a look that is simple and chic.

19) Ballet Brilliance

Chic blonde in black ripped jeans and grey oversized sweater

It’s classy meets edgy when oversized luxury meets ballet flats and ripped jeans photo: titicrafty.com)

Those lace-up ballet flats from the fall are back in style and trendier than ever, especially when paired with ripped skinny jeans and an oversized off-the-shoulder grey sweater. This look is simple and casual enough to wear comfortably during the day, yet classy enough to take you into the evening with style.

20) Loosely Layered

Trendy blonde in black leggings and loose grey oversized top

Let it all hang loose in simple leggings and an oversized off-the-shoulder top (photo: mitzitup.com)

For sunnier days that require a little less warmth, opt for layers of soft, comfortable fabrics to create a chic, effortless look. Basic black leggings and a fitted black tank top act as a blank canvas underneath a loose oversized sweater made of brushed cotton. The effect is easy-going yet elegant, polished off with slouchy black leather boots and a large carry-all tote bag.

21) Winter Chic

Cute blonde in black leggings and loose blue oversized sweater

Brave the winter chill in style with oversized wool and thick insulated leggings (photo: halliejophotography.com)

No matter where you stand on the whole ‘leggings as pants’ debate, you have to agree: they’re one of the most comfortable pieces of clothing you can wear. The key to wearing them during the winter months lies in the fabric. Look for a pair that is thicker than usual to provide extra insulation and also keep you properly covered. This outfit is as simple as it is chic, with black leggings worn underneath a loosely oversized grey ribbed sweater and cute lace-up brown boots.

Wearing Oversized Sweater Dresses

22) Versatile Style

Stylish woman in a black woolen oversized sweater and brown coat

An oversized sweater easily turns into a little black dress with the right accessories (photo: instagram.com)

A large, voluminous coat is a winter style staple and a sure way to amp up the glamorous factor of any outfit. Make the most of the coverage and show some skin elsewhere in your ensemble. Here we see an oversized woolen sweater turned into a little black dress by the stylish addition of knee-high leather boots. This look is guaranteed to turn a few heads in your direction and earn you some serious style points.

23) Thigh-High Drama

Chic brunette in a grey oversized sweater and faux-fur coat

Create some drama with a faux-fur coat, thigh-high boots and an oversized sweater (photo: junesixtyfive.com)

Nothing says “look at me” quite like a pair of sexy over-the-knee boots… and when they’re made of trendy black suede, even better. An oversized grey ribbed woolen sweater is worn over a peek-a-boo black lace bralette and black mini skirt. For an extra dose of drama, a statement coat in black faux fur is draped elegantly over the shoulders.

24) Berry Nice

Beautiful brunette in a berry-colored oversized sweater and burgundy boots

Make a bold statement in a berry-colored oversized sweater which doubles as a dress (photo: somethingnavy.com)

Just because the temperature has dropped doesn’t mean you can’t still show off some skin. An oversized sweater easily transforms into a dress, beautifully enhancing your female silhouette while still keeping you warm and cozy. This slinky deep berry number is paired elegantly with thigh-high burgundy suede boots and topped off with a statement handbag in faux fur.

25) Turquoise Dream

Classy brunette in turquoise oversized sweater and black thigh-high boots

A turquoise sweater dress hits all the right style notes for stylish winter dressing (photo: thefashiontag.com)

This eye-catching ensemble shows off the versatility of an oversized sweater. With a delicate mesh lace slip peeking out underneath, this turtleneck sweater becomes a full outfit. Polishing off the elegant look is a pair of thigh-high boots in sexy black suede as well as a black leather satchel and delicate gold jewelry.