style a winter sweater

5 Tips on How to Style a Winter Sweater

In Fashion Blog, Seasonal & Travel Fashion Tips by shubham JL

The changing season’s drop in temperature means that sweater weather is finally upon us. Colder seasons allow for more opportunity to play around with fashion by incorporating darker colors, warmer materials, and additional layers into your wardrobe. Sweaters are a staple in every winter wardrobe and can easily be styled with dozens of different items and accessories to create a chic look.

Winter sweaters are incredibly versatile. To make it easy on you, we have five styling tips for styling a winter sweater:

  • Keep it casual
  • Work-ready
  • Streetwear
  • Night out
  • Extra warm

Keeping each of these styling tips in mind when choosing your winter sweater outfit will make getting dressed easy, so you can avoid the “I have nothing to wear” situation.

There are many things you can wear with sweaters, and pairing it with different pieces and accessories from your closet will help you create a look for every occasion. By getting creative with your styling, you’ll be ready to step out in your favorite winter sweater all season long. Keep reading for five tips on how to style a winter sweater!

5 Tips on How to Style a Winter Sweater

Keep It Casual

By styling your winter sweaters with some signature casual pieces, you can create the perfect look for relaxing at home or running your weekly errands.

Boyfriend Jeans

Boyfriend jeans offer a comfortable and relaxed fit that pairs great with a variety of winter sweaters. These jeans err on the baggy side, so they are great for moving around town and chilling at home with friends. Levi’s has some great fits for every woman that will help you to achieve that casual look.


Some days (ok, most days), the thought of putting on even the most comfortable of jeans is beyond imagination. Enter in leggings. Leggings are loved by women everywhere for being stretchy and comfortable but still can be dressed up with the right styling.

Pair your favorite baggy or fitted sweater with a pair of leggings, and you’ll look put-together while still being couch comfy. No Nonsense carries leggings in a variety of colors that you can pair with your favorite winter sweaters.


Whether you are heading out to the gym or running errands, sneakers are now a popular shoe for fitness and streetwear alike. Grab your favorite trendy pair and sport them with some leggings and a sweater, and you’ll like winter chic as you move about town.

Nike is a great option for both the gym and everyday wear.

Work Ready

Heading to work during winter can be a drag because not only are you facing your commute but suddenly, your alarm is going off, and it’s still pitch black outside! Try styling your coziest winter sweaters with some chic pieces to bring your office look to life to help get motivated.

Pencil Skirts

To pair your sweater with a pencil skirty, try opting for a sweater that is a bit more fitted or if you prefer baggy, make sure it can be tucked into the front or side of the skirt. Patterned pencil skirts look great with solid-colored sweaters and help to add a pop of color.

Choosing a material like a tweed will also add an extra layer of warmth during those particularly chilly months. Doublju pencil skirts are affordable enough to buy a variety of colors to mix and match. 


If you know you’ll be spending extra time outdoors on your way to work, it’s a good idea to add some tights under your pencil skirt. Tights have become one of the most fun wardrobe items to play around with, as they now come in so many different materials and colors.

If your sweater and skirt are neutral in color, style them with a pair of chic, patterned tights to amp up your look. Many tights, like these from Lamibaby, come lined with fleece to keep you extra warm and comfortable all day.


Earrings are a quick and easy way to class up any outfit. Sometimes strong statement jewelry can be overwhelming in the workplace, so try wearing a pair of cute studs or elegant hoops, like these from Amazon. Gold and silver are always great materials that pair well with a variety of fabrics.


Work can have you on your feet all day, so wearing a shoe that’s cute but comfortable is key. As you may be rocking some other strong statement pieces, keep your shoe subtle. A classic black leather flat like these from Tory Burch will look great with any style.


Heading out for lunch or dinner with friends means you’ll want to look chic and modern. Winter streetwear fashion offers so much opportunity for exploration, so don’t be afraid to pair your sweater with some fun and funky items.

Skinny Jeans

Skinny jeans are a staple of the female wardrobe and for good reason. These jeans are form-fitting but still manage to be comfortable. Rocking a pair of dark denim or black jeans like this classic style from Levis will look edgy and sophisticated with your winter sweaters.

Flared Jeans

Alright, not everyone is ready to jump on the flared jeans bandwagon, but they are still worth noting. For many of us, this denim is too reminiscent and prefer other popular jean styles for women. But this old-school trend is back in a very big way.

If you’re in a daring mood, then throwing on a pair of flared jeans will have heads turning. As flared jeans draw a lot of attention, try styling them with a fitted sweater on top and relaxed accessories. Check out Bisual‘s flared jeans, which have a more subtle flare for those just getting their feet wet in this department.


Ankle booties will elevate your entire look without making things to formal. You can wear them with a heel or as a flat, and they pair great with any sweater. The Women’s Rate Boot by Dr. Scholl’s is comfortable enough to be worn all day but is still super cute and on-trend.

Night Out

Winter sweaters are not just for hanging at home and staying warm on the go. When styled correctly, you can easily take your coziest winter sweater and wear it to a night on the town. Focus on styling with form-fitting pieces and eye-catching accessories.

Mini Dress

Mini dresses are a favorite outfit for a fun night out, but in the winter, you need to think twice if your favorite dress is worth potentially freezing to death over. By throwing a warm and cozy sweater on over your favorite mini dress, you are sure to stay cute but toasty as you go bar hopping.

Make sure that your sweater falls around waist or hip length and that the bottom of your dress can still be spotted peeking through. For an ideal fit, check out these bodycon dresses by SheIn.

Over-the-knee Boots

Your top isn’t the only part of you that needs to keep warm while heading out during winter. A bare leg can leave you shivering through the evening, so to keep warm, throw on a pair of over-the-knee boots.

This style is all the rage this season and will keep your legs nice and warm while also looking incredibly chic and sexy with your mini dress. Steve Madden’s Gorgeena boot pairs great with a sleek mini dress.


There comes the point in winter when dressing cute and not freezing to death does not seem doable at the same time. But don’t despair. You can still wear your cute and comfy sweater AND stay warm by throwing on some extra layers to help you get by.

Puffy Jacket

Sometimes you need to take your warm layering to the next level. For those of us living in locations that can get to sub-zero temperatures during the winter, throwing on a thick, puffy, down jacket, like this one from Wantdo, is going to be your best bet for surviving the cold.

Using your sweater as a base layer and adding the puffy on top will have you feeling like July in the middle of February.


Sporting a vest on top of your sweater is a super cute way to show off the sweater while adding an extra layer of trendy warmth. Down and padded vests are a great option or something that comes with a hood. Check out this simple style from Fuinloth for inspiration.

How to Style a Cropped Sweater in Winter

Many of us cannot leave our cropped tops behind, even in the dead of winter. To style your cropped sweater during this season, you’ll want to reach for some well-fitted overlayers and the right pants to keep warm.

High-rise Jeans

You MUST pair a cropped sweater with high-rise jeans in winter. It’s really the only way to rock a cropped sweater in the winter. Your midriff will thank you when it’s not hanging out to shiver in the winter cold. Choose some dark fade or black jeans from Levi’s that fall below the sweater’s cut.

Leather Jacket

Leather jackets are a great top layer for a cropped sweater because they are fitted, warm, and very stylish. Choose a classic brown leather or go with black. Any style will look great with your cropped sweater. This simple cut by Tanming comes in tons of different colors, to make styling easy.

(Want more jacket options? Check out these 10 jackets to keep you hot in the winter!)

How do You Accessorize a Sweater?

Accessories can make or break an outfit. Having some warm winter gloves and a handful of go-to accessories that work with your sweaters ,will make it easy to choose a couple on the way out the door! Keep these in your style locker for winter sweater days.


We all know that showering tends to take a back seat during the winter months. Having unwashed hair is no problem when it’s cold out because you can easily toss a beanie on to look put together. Brush out the ends of your hair, and you are good to go! Carhart is a great brand, well-known for its warm and durable beanies.


Nothing will ruin your day, like feeling a cold breeze down the back of your neck. Keep those vulnerable parts warm while still looking chic by adding your favorite wrap or infinity scarf to your ensemble. Amazon has a huge selection to choose from. Just make sure you layer different materials as a whole world of knitting could look a bit overwhelming.

Statement Necklaces

To dress up your winter sweater for an evening out, pair it with a flashy statement necklace. Strong pieces in gold or metallic look classy and interesting in contrast with your more relaxed sweater. This affordable 12-piece set by Hicarer will leave with tons of styling options.

Floppy Hat

Floppy hats are another popular winter accessory that poses a nod to the fashion of the 1960s and 70s. Floppy hats will help keep your head extra warm while adding a retro flair to your outfit. You can find the right fit for you by browsing the wide variety of hats on Amazon.

Final Thoughts

Winter fashion provides countless styling options. If you are wondering ‘what to wear on Christmas Day’ check out that article! But you can totally wear your favorite winter sweater as the base, and can create endless looks by just adding in a few key accessories. Layering different colors and patterns can prepare you for day or night, formal or casual.