20 Cute Outfits With Sweaters to Wear This Winter

Winter is a great season for fashion, but let's be honest — it presents challenges. After all, it can be hard to put together outfits that look fabulously stylish for work days, casual weekends, and nights out while also staying warm. Sweaters are the obvious solution, but what should you wear them with to look elegant, sexy or sophisticated? To inspire you to think past the usual jean-and-sweater combo, we've rounded up some of the best outfits with sweaters from street style stars. Step up your sweater game this winter with these awesome sweater outfits that answer the question, what should you wear with a sweater this winter.

01
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Sporty Chic Look for the Office

Street style work outfit
A striped sweater is a winter essential. Brian Dowling/Getty Images

Ski sweaters with stripes and snowflakes are a popular winter fashion trend. Wear yours beyond weekend by pairing a sporty pullover with sophisticated black trousers for work. Add a beautiful bag and classic black pumps to add polish to this winter-ready office outfit.

02
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Monotone Dressing

Woman in beige sweater and pants
Monotone dressing is a thing. Daniel Zuchnik/Getty Images

Monotone dressing (wearing the same color from head to toe) is one of the season's biggest fashion trends, seen everywhere from celebrity fashion blogs to street style photos. Style a sophisticated outfit for work or polished casual wear, by matching a neutral sweater with tone-on-tone pants. We love the way the sweater is tucked into the waistline here, creating a flattering silhouette.

03
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Date Outfit: Soft Sweater and Mini-Skirt

Yellow sweater and short skirt outfit
A cheery yellow sweater can be worn with all your basic separates. Christian Vierig/Getty Images

When the weather cools, your date outfits need to get cozier. A soft, touchable sweater in a cheerful color is the perfect date night topper for a leg-baring mini-skirt.

04
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Striped Pants and Pink Sweater

Street style outfit striped pants pink sweater
Candy pink over stripes is a recipe for style. Christian Vierig/Getty Images

Want to make a candy pink sweater look downtown chic? Pair it with graphic black and white bottoms, as pictured here. We love the extra detail of sleeves peeking out on this street style outfit for winter.

05
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Faux Fur and Cargo Pants Outfit

Winter style in faux fur and cargo pants
Winter style in faux fur, a sweater and cargo pants. Christian Vierig/Getty Images

Today's most fashionable street style stars know how to mix luxurious pieces with basic separates, to create outfits that feel fresh. Here, a glamorous, faux fur jacket layers over a soft, loose-weave sweater and simple cargo pants, for a high-low outfit that is sure to turn heads. We love the addition of pearls and silver booties, which add further contrast and fun to this fabulous weekend or party look.

06
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Graphic Skirt With Solid Sweater

Red sweater and graphic skirt outfit
Style a fuzzy sweater with a skirt and matching booties for work. Daniel Zuchnik/Getty Images

Prints are a major fashion craze now. If you usually gravitate to solids, wearing a patterned skirt with a solid top is a great way to participate in this trend. Here, a fuzzy, solid-colored sweater and matching accessories create a pulled together look, worn over a graphic skirt in a neutral palette.

07
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How to Wear White Jeans in Winter

Street style white jeans
Wear a tweedy sweater over white jeans this winter. Christian Vierig/Getty Images

Here's proof that you can wear your white jeans right through the winter months, when you style them for the season. A nubby grey sweater and a tone-on-tone tweed jacket are the perfect layering pieces for a go-to pair of cropped white denim jeans.

08
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Pantsuit Outfit for Winter

Woman in red pantsuit
The pantsuit returns. Claudio Lavenia/Getty Images

Call it the influence of Hillary, or the desire to have fun with fashion, while still staying office-appropriate (and warm) for winter. Whatever the cause, pantsuits are the new black. Wear a colorful pantsuit over a ribbed sweater in a matching color, for a trendy one-color outfit for work that's anything but boring.

09
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Silver in the City

Silver street style outfit
Silver and grey are a beautiful match. Matthew Sperzel/Getty Images

Frosty silver tones feel right when the weather is cold. Style a cozy, elegant outfit that works for everything from gallery-going to dinners out, when you wear a thick, silver-grey sweater over a metallic-toned skirt and matching accessories.

10
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Dressed Up Sweater and Skirt Outfit

Pink sweater and skirt outfit
Wear a sporty sweater over a dressy skirt. Edward Berthelot/Getty Images

The pleated maxi skirt continues as a popular fashion trend that's ideal for wearing to parties this winter. Keep your look stylish but cozy, when you pair a colorful longer skirt with a sweater in a matching color or pattern, as pictured here.

11
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Evening Outfit With a Chunky Sweater

Date outfit in sweater and long skirt
Winter date outfit in a cozy sweater and long skirt. Christian Vierig/Getty Images

Have you got a chunky, over-sized boyfriend sweater that you usually save for cozy weekends? Here's inspiration for wearing it out to parties and dinners this winter, with an elegant maxi skirt and dressed up accessories.

 

12
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Cute Winter Date Outfit

Date outfit in leather skirt and white sweater
A chunky sweater makes a leather skirt look friendly. Kirstin Sinclair/Getty Images

Want a go-to outfit you can wear on all your dates this winter? Look no further than this perfect combination of a snuggly, white cable-knit sweater and a sexy leather mini-skirt. Wear this cute winter date outfit with trendy, tall black boots for warmth and style.

13
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Shades of Grey

Woman in grey sweater coat
Shades of grey outfit. Christian Vierig/Getty Images

Neutral shades tend to convey elegance, making them perfect for creating sophisticated work outfits. A classic cable-knit sweater in soft grey pairs beautifully for the office this winter with matching grey trousers and a tone-on-tone sweater coat.

14
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Say It in Stripes

Street style in stripes
Street style in stripes. Kirstin Sinclair/Getty Images

Stripes are a perennial winter favorite for sweaters. Here, a classic black-and-white striped sweater meets its glorious match in a multi-colored striped skirt. The combination is unexpected, confident and fashionable.

15
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Work to Cocktails Outfit

Woman in grey sweater and skirt
Look chic for work in a slim sweater and skirt. Timur Emek/Getty Images

When you know your day will take you from work to cocktails or dinner with little time to stop and change, this one-color sweater outfit has you covered. A light-weight, form-fitting turtleneck sweater is streamlined enough to wear to work, tucked into a wrap-style skirt. Wear it to the office with classic mid-heel pumps and a leather tote, then swap your daytime accessories for high heel boots and a cute clutch purse for the transition into evening.

16
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In the Pink Party Outfit

Casual outfit in pink sweater
Casually cute in a pink sweater. Mireya Acierto/Getty Images

When winter parties beckon, we all want an outfit that will look fabulous and still keep us toasty warm. Achieve your winter style goals in this edgy-meets-elegant outfit of a nubby pink knit sweater and fashion-forward, shiny leather pants. Playful accessories that match (or complement) your sweater keep this look fun and flirty enough for date nights, too.

17
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Casual Chic Winter Weekend Outfit

Red sweater and jeans outfit
Weekend chic in ripped jeans and a bright sweater. Christian Vierig/Getty Images

Winning weekend style can be as easy as a cozy sweater and ripped jeans, when you pay attention to accessories. Here, a basic jeans and sweater outfit are elevated by a colorful belt and fabulous ankle boots in a trendy floral print.

18
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Special Cable Knit Sweater

Street style in white sweater and jeans
A pretty white sweater looks classic over ripped jeans. Timur Emek/Getty Images

Sometimes, all it takes is one special piece to elevate your whole outfit. Here, a simple combination of a white sweater and ripped blue jeans looks suddenly street-style-worthy, when you choose a sweater featuring pretty detailing and unexpected proportions (those shoulders are to die for).

19
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Weekend Sweater and Leather Skirt

Sweater and leather skirt outfit
Layer a casual sweater over a leather skirt for instant style. Edward Berthelot/Getty Images

Want to dress up your favorite weekend sweater, and wear it out to glamorous parties and dinners? Layer a cozy knit pullover over a leather midi skirt and wear with classic black accessories, for a chic evening-out look that telegraphs confidence and style.

20
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Puffer Jacket and Track Pants

Sporty style in a puffer jacket and sweater
Sporty winter style in a puffer jacket and bright sweater. Christian Vierig/Getty Images

Fashion editors have declared the puffer jacket the favorite coat of winter. Here, a basic puffer coat is layered over a bright yellow sweater, sporty track pants with a matching stripe, and sexy high heels in a matching color, to create an easy, comfortable winter outfit that tracks as surprisingly sophisticated.