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.

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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.

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

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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.

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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.