14 Sweater Outfit Ideas For Chilly Weather

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As we begin to enjoy the cooler weather, it's that time of the year again when we pull out our favorite sweaters. For many, these are among the most beautiful months of the year--the sun sets a little earlier on the horizon and a cool, crisp (and soon to be chilly) breeze fills the air. So, with the changing of the seasons, must also come a wardrobe change! You probably have already long since said goodbye to summer, but now it’s finally time to get cozy!

14 Ways To Style Your Favorite Sweater

So, it is finally time to put your favorite sweaters to good use as we all begin to enjoy the cooler temps. You can choose from a nearly endless selection of styles and fabrics, all of which will make this comfy, box-shaped sweater look even more stylish and functional. The great thing about a chunky sweater is that not only is it versatile, but it can be the memorable centerpiece for so many outfits!  

Wear A Sweater Dress On Date Night

Sweater Outfit Ideas - Date Night Sweater Dress

Have a favorite sweater dress? Wear it! Or, if you have a thick sweater that is both long and oversized enough, wear it as a dress this season. This is probably one of the easiest and most comfortable ways to style a sweater since all you have to do is put it on! However, depending on the length of the sweater and how cold it might be, consider wearing a pair of tights for some extra warmth or coverage. Wearing it as an oversized dress also gives you the flexibility to dress it up or down, especially with your choice of shoes. You can wear a chic black heel for date night, leather riding boots for a day out with your girls, or (our favorite) styled with tall knee-high boots and a wool coat to stay extra warm.

Wear A Sweater In An All-Day, Everyday Kinda Way

Sweater Outfit Ideas - Everyday Casual Outfit

A cropped sweater is a fun variation on the classic style and is great to have in your closet, especially for a cute outfit when you’re short on time. Wear this sweater with your favorite pair of black leggings for extra comfort and paired with white sneakers. Or, if you want to dress it up a bit, try a pair of black leather booties. This is a great outfit when you’re lounging at home, on a day full of errands, or for a shopping day that you’d want to get a little dressed up for! 

Wear A Sweater With A Chic Mini Skirt

Sweater Outfit Ideas - Plaid Skirt and Turtleneck

A chunky turtleneck, cropped or not, will look great with a plaid mini skirt. Buying a skirt with a neutral undertone—such as navy blue, black, or beige—can spice up your wardrobe, while also making your closet more versatile since the colors are easy to match. Try pairing it with tights if it’s a colder day, or if it’s still warm outside, show off those stems! Plus, wearing a heavier sweater with a skirt can still serve as a fun, casual look or a dressy one. And, if you don’t already have one, a plaid mini skirt is a must for a new, updated outfit rotation.

Wear A Sweater To Make Jeans Feel A Little Fancy

Sweater Outfit Ideas - Dressed Up Jeans

Flared pants have made a comeback this year and we think they are here to stay! This timeless style of pants can make a very simple outfit look chic—especially when paired with a sweater—and can be printed, denim, or the same material as your favorite business casual dress pants. Dress it up again with a black heel for a “fancy” day or pair it with all-white sneakers for a more relaxed look. Either way, consider keeping this outfit idea part of your everyday rotation.  

Wear A Sweater As Part Of Your Athleisure

Sweater Outfit Ideas - Comfortable Athleisure

Create the ultimate athleisure look with a sweater and your favorite pair of biker shorts. Of course, wearing a pair of black ones can go with any outfit, but also try out other seasonal colors, such as army green, chocolate brown, or even maroon. If you stick to classic black, take the opportunity to be more adventurous and wear a knit sweater in colors such as neon yellow, orange, or even a pretty blue! Either way, you’ll certainly look cute and be comfortable with this look. 

Wear A Sweater To Be Simple & Chic

Sweater Outfit Ideas - Simple and Chic

You can easily feel comfortable and chic during the cooler months when pairing a chunky sweater with your favorite go-to denim and leather boots. Any type of denim will work—boyfriend jeans, skinny jeans, flared jeans, ripped jeans, black denim—really, whichever you feel like wearing that day! The leather boots with a sleek tip at the toe tie the outfit together by making it feel more refined. And, while you’re at it, put your hair up in a chic, high bun to let your favorite gold earrings show. This outfit is great for a casual gathering with friends, a dinner date, or even a day in the office (if jeans are acceptable!). 

Wear A Sweater A Little Tucked In

Sweater Outfit Ideas - All Black French Tuck Sweater

We all know that great French tuck that Tan France from the Netflix series, Queer Eye, talked about so often. If you haven't already tried this trend, why not try it now? A French tuck simply means to tuck a small portion of your top into the waistband of your bottoms—dress pants, skirt, jeans, denim shorts, you name it! In this case, put on your favorite sweater with a pair of black denim. (Remember, however, you can’t fully tuck in this style of sweater due to its thickness.) This outfit can be a little edgier, especially if paired with pointy boots or a pair of loafers, or you can also keep it more relaxed with your favorite sneakers. Wear it for a fancy evening with your partner or a cool weather picnic. 

Wear A Sweater To Embrace The Y2K Trend

Sweater Outfit Ideas - Y2K Inspired

Baggy jeans have stayed on trend throughout the year and simply make an outfit stand out. Style these jeans with a sweater—the more oversized, the better—to really get the vibes going. To fully embrace the Y2K trend, you need bright or bold accessories to complete the look, such as a claw clip or a printed bag (or both). For a casual day out, put on a pair of all-white platform sneakers. For a more dressed-up outfit, wear platform boots. The great thing about wide leg jeans or bottoms is that they can easily create a bold look–great for any time of the year. 

Wear A Sweater Over A Dress

Sweater Outfit Ideas - The Bodycon Dress Trick

To make the most out of the items already in your wardrobe, wear a black bodycon dress with any of your sweaters to give the illusion that you’re actually wearing a skirt. Now, your little black dress doesn’t have to be saved for a fancy night out (or date night!), but can be worn on a chilly afternoon or evening, making it a versatile closet staple. This outfit is perfect for a dinner party with a pair of heels or a brunch with friends and family if paired with your favorite boots. 

Wear A Sweater To Play With Color

Sweater Outfit Ideas - Playful Color With Trousers

Dress up a sweater with a pair of dress pants. Yes, black and beige are the standard colors to wear and sure, no one will ever go wrong with them. However, let’s spice it up this season with a pair of dress pants that are chocolate brown, burnt orange, mauve, or even off-white. Like many of the outfits on this list, this one is easy to dress up for a more formal look or dress down for a casual, chic outfit. It all depends on how you’re feeling and what shoes you decide to put on that day! Shoes to consider are ankle booties with a kitten heel, colored pumps, or even sneakers to match.

Wear A Sweater Layered Over A Button-Up Shirt

Sweater Outfit Ideas - 90s Grunge Throwback

For those extra chilly days, or the ones where you can’t decide if you feel like being preppy or more grungy, try layering a sweater over a plaid shirt. When you match it with a cropped sweater, the plaid underneath will be more visible, making it feel relaxed and casual, especially when paired with jeans. For a more chic variation, layer a sweater over a collared shirt alongside dress pants or a skirt, ala Gossip Girl.

Wear A Sweater With A Satin Skirt

Sweater Outfit Ideas - A Dressy Event

For a chic twist on a classic pairing, try combining a heavyweight sweater with the soft sheen of a satin skirt. The long skirt and tall boots keep your legs warm during even the coldest days, but the satin keeps the look from feeling too heavy. If your color palette is muted, play with bold accessories. Or, if you prefer a more understated look, match your handbag to your boots. This look is perfect for everything from a family dinner to a holiday party.

Wear A Sweater As A Vest

Sweater Outfit Ideas - Sweater Vest and Corduroys

Yes, a sweater vest counts in this outfit roundup! Layer your favorite vest over a clean white shirt for that slightly undone look. For a play on patterns, try a pair of printed pants; to try different textures, create a look around corduroy. Classic accessories, like a leather belt or boots, simply finish the outfit in a put together, yet I-wasn’t-trying sort of way.

Wear A Sweater With Overalls

Sweater Outfit Ideas - Warm At The Farmer's Market

You can’t let the cold weather pass you by without taking advantage of another trend this year—overalls! This denim set is easy to style with a neutral sweater and coordinating accessories. Grab your favorite reusable tote, and you’re all set to head to a local farmer’s market for your favorite vegetables.

Figuring out how to style a chunky sweater is more simple than you might think and now you have options to try out. Feel good about yourself, stay cozy, and warm up with any of these outfits!

Angela deMesa

Lover of French fries, travel, fashion, and the comfiest workout clothes.  She is from the beautiful, San Francisco Bay Area and currently resides in Barcelona, Spain.  In 2018, she followed her passion for writing and published for the first time in a tourism magazine called Barcelona Connect.  She continues to contribute to various online and print publications.  In her free time, she enjoys doing yoga, teaching an occasional spin class, and a glass of red wine with a good book.


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