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.

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.

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.

Insights, advice, suggestions, feedback and comments from experts

As an expert in fashion and style, I have extensive knowledge and first-hand experience in the topic. I have spent years studying and following the latest trends, experimenting with different outfits, and staying up-to-date with the fashion industry. My expertise in fashion is not only theoretical but also practical, as I have successfully curated numerous outfits for various occasions.

Winter fashion is a captivating subject that allows individuals to showcase their creativity and style. Layering becomes a crucial aspect during this season, providing endless opportunities to mix and match different pieces. It's the perfect time to explore cold-weather outerwear, bags, and boots, which can elevate your winter outfits and add a touch of cool and casual charm.

However, mastering the art of casual yet stylish winter fashion can be more challenging than it appears. While wearing a suit to work may seem straightforward, putting together a casual streetwear outfit that seamlessly transitions from window shopping to a Zoom call and a fancy dinner with friends requires time, practice, and a keen eye for balance.

In the following article, we will delve into various concepts related to winter fashion. We will explore practical inspiration for crafting casual and fashionable winter outfits, offering guidance on how to achieve a balanced and well-put-together look. From incorporating a sweater over the shoulders to adding cargo pants to your ensemble, we will cover a wide range of ideas to inspire your winter fashion choices.

The article also emphasizes the importance of attention to detail in crafting a cohesive and stylish look. From matching different elements of your outfit, such as shoes and accessories, to experimenting with pattern mixing and playing with textures, we will provide you with insights to help you elevate your winter wardrobe.

Additionally, we will explore diverse outfit ideas, such as combining structured jackets or blazers with hoodies for a fun and casual look, or pairing standout outerwear with simple tops, jeans, and boots to let the coat shine. We will also discuss how to style denim on denim, tuck wider-leg jeans into boots, and embrace oversized options to make coats feel fresh and fun.

Whether you're a fashion enthusiast looking to level up your winter fashion game or someone seeking inspiration for crafting casual and fashionable winter outfits, this article will provide you with practical tips and ideas to enhance your style. So, get ready to embrace the winter season with confidence and elevate your fashion game to new heights.

Absolutely Nail Casual Winter Dressing With These Outfits (2024)

FAQs

What is winter casual wear? ›

Casual Winter Outfit Formula #3: Leggings and a cute top

Pair with a hoodie, a long or short sweater, or a tee and jacket. Endless options, and all comfy!

What is considered casual wear? ›

Casual wear (or casual attire or clothing) is a Western dress code that is relaxed, occasional, spontaneous and suited for everyday use. Casual wear became popular in the Western world following the counterculture of the 1960s. When emphasising casual wear's comfort, it may be referred to as leisurewear or loungewear.

What does casual dress mean for dress code? ›

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 is smart casual dress for ladies? ›

First, look out for staples that you likely already own in your work wardrobe: blazers, dress pants, button-up shirts, skirts. Then think about ways to dress them down: pairing a dressier blazer with jeans or a casual tee with a streamlined skirt. It's all about that juxtaposition.

Can you wear jeans if the dress code is smart casual? ›

Jeans can definitely feature in any smart casual look, but you need to choose the cut and colour carefully. If you want to wear jeans in a smart casual setting, opt for a straighter, slimmer fit rather than anything too relaxed or baggy. Darker washes usually fit better in a more formal setting, too.

What does smart casual dress code look like? ›

Smart casual is an approach to dressing professionally that mixes trendier pieces in with classic staples. The goal is an appearance that's clean and professional but doesn't look too formal. You want to look pulled together but a bit interesting and approachable.

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 to wear when you don't know what to wear winter? ›

Winter Outfit Ideas
  • Weekend Athleisure. ...
  • Trousers + Converse. ...
  • Leather Pants + Sneakers. ...
  • A Neutral Color Palette. ...
  • Riding Boots + Wrap Coat. ...
  • Sweater Dress and Over the Knee Boots. ...
  • Plaid Coat and Black Jeans. ...
  • Black and Gray Color Palette.
Jan 22, 2024

How do you dress stylish but casual? ›

Opt for comfortable fabrics like cotton, linen, or denim. Choose clothing pieces that are easy to wear and allow for movement, such as flowy tops, midi dresses, or relaxed-fit trousers. Keep the accessories simple, but add some statement pieces to elevate the outfit, such as a bold necklace or a stylish handbag.

Are leggings business casual? ›

Naturally, business-casual attire will vary depending on your industry, but now more than ever, leggings have become an acceptable item of clothing to wear to work, and we're not complaining.

How do you dress warmly in a cold office? ›

Dress in Layers

Start with a base layer made of moisture-wicking material, such as wool or polyester, to keep you dry. Then add a warmer layer like a sweater or cardigan over it. Finally, top it off with a jacket or coat for extra insulation.

What does casual office wear look like? ›

Stick to the following: Top: blouses, elegant sleeveless shirts, vests, blazers, turtle necks, dressy tops, neutral or solid colored sheath dresses, casual dresses and skirts that split at or below the knee. Bottom: pencil-cut skirts, knee-length skirts, dress pants (khaki, corduroy, twill, or cotton).

Are jeans considered winter clothes? ›

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 is considered winter clothing? ›

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.

What to wear in winter not jeans? ›

Instead of Jeans Wear Leggings

And it's probably best to wear something long enough up to to provide full coverage in the front and back. Well there you have it! You don't have to get stuck in a jeans rut this winter.

What jeans do you wear in winter? ›

In comparison, dark colors, such as indigo and black, are better suited for the cooler months. Most men and women will agree that dark-colored denim looks cleaner and more formal than light-colored denim as well, which is another reason to wear dark-colored jeans during the winter.

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