Absolutely Nail Casual Winter Dressing With These Outfits (2024)

Winter is a fun time for fashion, with tons of opportunities to layer. This is the moment to break out your best cold-weather outerwear, bags, and boots for some cool and casual winter outfits. But it can also be a time to level up your fashion game. There are more elements to your look, so it can take time and practice to make your winter outfit feel put-together and balanced. Casual but stylish winter fashion can be harder to achieve than it might seem: It's easier to wear a suit to work than it is to put together a casual streetwear outfit that works for window shopping, a Zoom call, and a fancy dinner with friends.

Keep scrolling for some practical inspiration for crafting casual and fashionable winter outfits.

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A Sweater Over the Shoulders

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The basis of this outfit is pretty simple: white tee, blazer, wide-leg jeans, and pointed-toe boots. But the Dior bag and the pop of color from a red knit sweater add dimension and surprise. If you like scarves, change it up by adding a sweater over your shoulders for a fashion-girl look.

How to Wear Red, According to InStyle Editors

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All the Details

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Crafting a "busy" look is a skill that can be difficult to master. You want to feel like the look is cohesive without becoming too much, so make sure the different elements match: white Adidas shoes with a white graphic tee, near-matching a brown jacket to a black skirt, and a silver bag to pair with the light gray in the shoes.

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Adding Some Cargo

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Cargo pants are having a moment, but they don't have to skew too casual with the right styling. Treat them like a very casual suit by combining them with a matching color on top, as with this bomber jacket, and get some color contrast with a plain top. A louder bag is a fun way to add color or dimension.

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Casual Business Chic

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For a fun, casual look that mixes in your more work-ready pieces, pair a structured jacket or blazer with a cashmere or cotton hoodie. The hood peeks out over the blazer and gives texture to the outfit. Sticking to neutrals, like casual sneakers and straight-leg jeans, will keep things subtle and easy.

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The Very Best Coat

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Granted, not all of us have a cut-out black leather coat. Absolutely chic. But this is the formula to use with any standout outerwear, whether it be animal print, puffy, or colorful: Wear a simple top (preferably one that peeks out at the top and sides), jeans, and a plain pointed boot.

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A Heavier Mini

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When the weather's not too chilly and you can get away with bare legs, pair a sweater or vest (in this case a pink Ganni) with a black mini and chunky black boots to match. This outfit's also a great way to show off some patterned tights when you need more coverage.

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Graphic Topping

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Another way to style a graphic sweater or vest is to let it be the standout piece in an otherwise neutral outfit. Here, a navy Louis Vuitton sweater takes center stage against a near-match plain black skirt and brown clogs (which add a little trendiness but still feel casual).

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Peak Fluff

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Fluffy coats aren't just fashionable, they're functional: a warm, woolen (in this case Burberry) coat can make a fashion statement just as well as it will keep you toasty warm. You may not always want to pair it with a see-through dress on the bottom for contrast, but you can still add dimension by going with something feminine or structured.

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Glittery Details

If it's a casual party look you're after, give your jeans or pants a little sparkle. Here, the pants bring a stronger shine, while the blazer has a more subtle matching sparkle. The buckle on the shoe and the hardware on the bag tie everything together.

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Denim on Denim

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If you'd like to match your top and bottom in a lighter color, try the never-out-of-style Canadian tuxedo. Go for a shacket or denim jacket and some wide-leg jeans with a similar (though not identical) wash. Then keep the rest of the outfit simple.

The Best Ways to Wear a Denim Jacket with Jeans

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Tucked Boots

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You might be familiar with tucking thinner pants (like a skinny or straight leg) into boots, but try experimenting with wider-leg jeans instead. It takes a little practice to achieve that perfect tuck, so use thicker boots with room in the ankle and tie securely. Keep the rest of the look tonal, as with this blue sweatshirt over blue jeans.

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A Coat-Dress

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As an alternative to a long, ankle-grazing coat, try two matching separates that can also function as outerwear. Here, a green leather jacket and matching skirt make for a warm outfit during a commute, but they also serve as a modern suit alternative at work or an event. Wear a lighter T-shirt under the jacket in case it's warm inside.

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Decorative Denim

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If fall and winter are your favorite seasons because you have the absolute best jeans, this is the time to break them out. Patterned denim is fun, particularly when cut like this. Style them as the focal point of the outfit, with a fun matching bag, cool cropped jacket (so you can see your entire bottom half), and plain shoes that elongate your legs.

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Perfect Pattern Mixing

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It can be tough to decipher which patterns in your wardrobe are best for mixing. For example, a zebra bag and a bright pink-and-blue jacket don't sound like they'll go together, but that's the fun of experimenting with your closet. If you treat your animal-print items as neutrals, you're still keeping the look to one standout piece, just with a surprising choice of accessories.

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Cocoon Shaping

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Another way to make the most out of winter—especially if you're not interested in playing with color—is to grab a coat with a unique shape. This gray coat still stands out because of its high-water hemline and cocoon shape, paired expertly with a tonal gray look underneath.

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Going All-White

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White-on-white is a nice choice in the summer when the temps are higher, but resist the temptation to pack all your light colors away when it's cold. A white tonal look is still stylish in fall and winter, you just have to upgrade your cotton and linen to leather, knits, and heavier silk.

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Bucket Hats

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A bucket hat isn't the warmest choice for headgear—that would probably be a beanie—but your hat and shoes are good places to add more modern elements to an outfit. Here, it's both, with the hat and chunky platforms giving the otherwise basic tube top and wide jeans a more edgy feel.

9 Casual Bucket Hat Outfits That Are Totally Wearable

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Oversized Options

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When in doubt, a pretty surefire way to make a coat feel fresh and fun is to buy it one size above what you normally take. To combat the bulk, style it over a more fitted, streamlined outfit so you don't feel like it's swallowing you up.

Absolutely Nail Casual Winter Dressing With These Outfits (2024)

FAQs

What do you wear in winter casual? ›

For a fun, casual look that mixes in your more work-ready pieces, pair a structured jacket or blazer with a cashmere or cotton hoodie. The hood peeks out over the blazer and gives texture to the outfit. Sticking to neutrals, like casual sneakers and straight-leg jeans, will keep things subtle and easy.

What is winter casual dress? ›

Wearing your high-waist denim with your ankle boots is the perfect cold-weather combo for casual winter outfits for date night. To keep it casual, opt for a long sleeve turtleneck or hoodie sweatshirt under your sweatshirt or leather jacket for extra warmth in the cold weather.

How do you dress simple but stylish in winter? ›

Look for fabrics like fleece, wool, and flannel to help you stay warm.
  1. A flannel shirt worn with a pair of jeans and hiking boots is a great way to show off your rocker style even when the weather is cold.
  2. A wool sweater worn over a skirt with leggings and knee-high boots is a cute, preppy winter outfit.

How do you wear a long dress in winter casual? ›

Maxi dresses are great worn all year long as they can be worn for a casual day out or a special occasion no matter the season. In the winter, you can pair them with cozy layers like a teddy coat or wool coat, but the shoes always complete the look.

What is the dress code for casual? ›

A casual dress code means that employees are permitted to dress in comfortable, informal clothing. Although the employees' comfort is a priority, certain standards are required—clothing must be appropriate and still professional.

What does casual dress code look like? ›

What is a casual dress code? Whether you're going out with your friends or you're heading to the office on a casual Friday, a laid-back style is the best way to go. The casual dress code typically consists of jeans, T-shirts, and cardigans. If you prefer skirts and sneakers, go for them!

What is smart casual winter? ›

Smart Casual Outfit Ideas For Winter

Team it with smart trousers, a plain t-shirt and then a buttoned-up cardigan in your colour of choice. Finish the look with flat shoes – even trainers might work on this one! Smart coat + thick jumper + jeans + boots.

How to dress attractive in winter? ›

Consider these fashion ideas for staying toasty while looking great this winter.
  1. Wear three layers. ...
  2. Keep it tight. ...
  3. Wear long coats. ...
  4. Accept that you can pair sweaters with skirts. ...
  5. Choose the right type of down. ...
  6. Invest in wool. ...
  7. Avoid cotton. ...
  8. Consider a statement coat.
Jun 7, 2021

How can I look classy in winter? ›

Essential items to consider include:
  1. Versatile winter coat – A high-quality, insulated, and preferably water-resistant coat is a cornerstone of winter fashion. ...
  2. Sweaters and Cardigans: Choosing items made from warm materials like cashmere can be layered for added warmth while adding elegance to the outfit.
Nov 16, 2023

What kind of pants to wear in winter? ›

Fit and Comfort

Cold weather pants shouldn't just be warm — they should let you move freely and be as well-fitted as they are stylish. Think thick denim, durable work pants, and thick cotton joggers. Remember, the goal is to be warm and comfortable.

What are two types of clothes you like to wear in winter? ›

In winters, we wear woollen pullovers and jackets along with long pants and stockings, while in summers, we wear cotton shirts that allow air to pass through or dry the sweat easily. In rainy seasons, we cover ourselves with raincoats that do not allow water to pass through.

What to wear on legs with dress in cold weather? ›

Rather than reaching for ballet flats or your favorite pair of sneakers, go with boots that hit just below or over your knee. It's a sneaky yet sleek way to shield your legs from harsh winds. Plus, if you opt for a longer-length dress or add a pair of tights, you'll have even more coverage.

What to wear on legs with dresses in winter? ›

Layering: Wear thermal leggings or tights under your dress or skirt for added insulation. Knee-High Boots: Pairing your outfit with knee-high or over-the-knee boots can provide warmth and style. Woolen Socks: Opt for woolen or thermal socks for extra insulation.

Can maxi dresses be worn in winter? ›

Turtlenecks. Layering is one of the best ways to stay warm in winter. For maxi dresses, you can wear a thin, thermal turtleneck underneath a summer maxi dress or wear a knitted turtleneck jumper on top. If you're wearing a jumper on top, make sure it's not too long or too short.

What kind of clothes do you wear in winter? ›

Winter clothes are especially outerwear like coats, jackets, hats, scarves and gloves or mittens, earmuffs, but also warm underwear like long underwear, union suits and socks.

Do you wear jeans in winter? ›

Jeans can help in keeping you warm during winter. But, not all jeans are built to handle winter. So, choose your winter jeans for women well. It could provide good warmth and style during winter.

What kind of clothes do you like to wear in winter? ›

We usually wear woollen clothes in winter. They do not allow the transfer of body heat to the environment and keep us warm. But, fabrics like cotton and linen are comfortable in the summer season.

How should I dress for winter in style? ›

Add a sweater or cardigan for insulation, and top it off with a stylish coat or jacket. Don't forget accessories like scarves, gloves, and hats for both warmth and fashion. Opt for winter-appropriate footwear, like boots, to keep your feet warm and dry.

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