Winter’s here, and what does that mean for all of us who love fashion? Time to cozy up, layer on, and strut through the chilly streets in style! Whether you’re a fan of oversized hoodies, chic coats, or comfy sneakers, we’ve got something for you. Here are some of the trendiest casual winter outfits that will have you feeling comfy, stylish, and absolutely warm from now until the snow melts. Let’s dive in and get inspired!
Cozy Oversized Fleece with Leggings & Platform Uggs

Is there anything better than wrapping yourself in an oversized fleece on a crisp winter morning? In this gorgeous ensemble, we see an extra-cozy cream sherpa fleece jacket paired with classic leggings. The look is topped off with a beanie and chunky platform Ugg boots. It’s the epitome of women’s cold weather comfort, with an effortlessly cool vibe. The leggings are a comfy choice that provides the perfect balance to the oversized jacket—ideal for running errands or enjoying a cozy coffee shop date.
This look also highlights how to create a great street aesthetic, with the platform boots giving an unexpected pop of edge. Want to up the ante? Pair it with cute mittens and a hot cocoa to complete the vibe. Comfy street styles never looked this chic!
Inspiration for Styling Looks: Celebrities like Hailey Bieber and Gigi Hadid have been seen rocking similar oversized fleece looks paired with leggings. To recreate this look for a casual day out, pair it with colorful mittens or swap the platform Uggs for comfy sneakers if you’re doing a lot of walking. For a more polished look, try wearing sleek black leather boots instead. This cozy vibe is easy to personalize—swap out the fleece for a different color or add some bold accessories to make it yours!
Sleek Turtleneck Sweater Dress with Skinny Black Jeans

Next, we have a look that is perfect for anyone looking to blend comfort with a touch of elegance. A long, taupe-colored turtleneck sweater dress paired with skinny black jeans and ankle boots. This look is perfect for a casual office day or brunch with friends. The slim jeans accentuate the figure while keeping it classy, and the turtleneck adds that warm hug we all crave during the colder months.
Women over 40, this look is just for you! It’s sophisticated without sacrificing an ounce of comfort. The simple addition of a long necklace keeps it chic and modern. If you’re looking to try women’s cold weather jeans in a new way, this pairing is ideal for a day when you want to dress up while staying incredibly comfy.
Inspiration for Styling Looks: This look is reminiscent of Victoria Beckham’s go-to winter style—simple yet effortlessly chic. To adapt it for a more casual occasion, swap the boots for comfy sneakers and add a stylish cross-body bag. If you want to personalize it, experiment with different turtleneck colors or add a bold belt to accentuate your waist. Perfect for a day at the office or a cozy lunch with friends.
Pink Oversized Sweater with Relaxed Denim

Sometimes, we just want to channel all the cozy vibes—enter this lovely pink oversized sweater paired with slouchy denim jeans. The looser fit of the sweater makes it both comfy and trendy, especially in the popular blush shade that’s popping up everywhere this winter. The relaxed jeans add that effortlessly cool touch. Women 2025 trends are definitely leaning towards comfortable fits, and this outfit is no exception.
To finish the look, casual slip-on shoes add a laid-back element. Perfect for those days when you need to grab groceries but still want to look put together. Are you a fan of the cozy, casual aesthetic? Give this combo a try!
Inspiration for Styling Looks: This cozy pink sweater look is something you might see on influencers like Negin Mirsalehi or Sincerely Jules. To recreate it, add statement earrings or a bold lip color for a little glam. If you’re heading out on a cold day, layer a long coat over the sweater to keep warm. Want to add a unique touch? Try cuffing the jeans to show off a pair of fun socks or swap the relaxed denim for tailored jeans for a slightly smarter vibe.
Neutral Long Coat with Blue Jeans & Black Boots

A classic winter outfit that’s hard to beat. The long, neutral-toned coat paired with blue jeans and chunky black Chelsea boots is a timeless winter staple. The turtleneck peeking from under the coat provides that much-needed warmth while keeping things stylish. This is one of those outfits that instantly looks put-together—even if you spent all morning battling bed hair and kids.
Women cold weather fashion is all about versatility, and this look transitions perfectly from day to night. It’s elegant, comfortable, and absolutely chic, making it an ideal choice for women on the go. Not to mention, these comfy leggings-style jeans are stretchy enough to keep you comfortable through a long winter’s day.
Inspiration for Styling Looks: This classic combination is often spotted on fashion icons like Meghan Markle, who favors versatile pieces. To make this look more casual, consider swapping the black boots for comfy white sneakers. Add a patterned scarf or a bright handbag to personalize the look and make it pop. For a business setting, swap the jeans for tailored trousers and add statement jewelry for a touch of sophistication.
Puffer Jacket & Scarf Combo with Relaxed Denim

Next up, we have an ultra-cozy puffer jacket paired with relaxed denim and a beanie. The jacket’s volume is perfectly balanced by the more relaxed fit of the jeans, making this outfit ideal for those cold days when you just want to stay warm but also make a statement. The scarf adds extra warmth and makes this outfit look even cozier—as if you’re wrapped in a fashionable blanket.
Cold weather fashion doesn’t have to mean sacrificing style for warmth, and this look proves it. It’s all about the puffer! Add some comfy sneakers to make this perfect for walking through snow-covered streets in comfort and style.
Inspiration for Styling Looks: Kendall Jenner is known for her relaxed puffer looks, often paired with cozy scarves for a chic touch. To recreate this style, you could add some fun winter accessories, like earmuffs or fingerless gloves. If you’re looking to adapt it for a dressier occasion, swap the relaxed denim for fitted black jeans and add heeled ankle boots. Personalizing the outfit could be as simple as choosing a colorful scarf or trying a puffer jacket in a metallic tone for extra flair.
Shearling Aviator Jacket with Grey Leggings

Let’s talk about baddie winter vibes! In this outfit, a shearling-lined aviator jacket paired with grey leggings offers that effortlessly cool look we all secretly want when we head out to grab coffee. The jacket’s structured silhouette makes it stylish, while the leggings keep it comfy. This outfit is ideal for someone who’s all about a minimalist yet edgy aesthetic—a perfect fusion of comfy and trendy.
Top it off with a pair of sunglasses for that true baddie look. We love seeing women embracing comfort without letting go of their own unique style—a trend we’re excited to see more of in 2025.
Inspiration for Styling Looks: Bella Hadid loves an edgy aviator jacket, and this look takes inspiration from her style playbook. To make this look work for everyday errands, you could swap the leggings for black joggers for an even comfier vibe. Adding combat boots instead of sneakers gives it a bolder edge. Want to make it your own? Try pairing it with colorful socks that peek out from your shoes or swap the aviator for a bomber jacket if you prefer a different silhouette.
Casual Hoodie & Coat Combo with Sneakers

You’re running late, and you just need something that looks good and keeps you comfortable—sound familiar? This outfit is perfect for just that. A cozy hoodie layered underneath a camel-colored coat, paired with black leggings and white sneakers. It’s the epitome of comfy street styles, especially with the clean, monochromatic palette that adds an extra edge of chicness.
Great for women of all ages, especially women over 40 who still want to look on-trend without compromising comfort. This outfit proves that sneakers and coats are a match made in heaven, and the leggings keep everything streamlined and modern.
Inspiration for Styling Looks: This laid-back combination is similar to the looks often worn by Rosie Huntington-Whiteley when she’s off-duty. To adapt this look for a more business-casual setting, switch the sneakers for ankle boots and replace the hoodie with a thin-knit turtleneck. Adding a colorful cross-body bag or some statement jewelry is a great way to make this outfit feel more personalized and a little less understated.
Teddy Coat & Cropped Sweater with Faux Leather Leggings

Who doesn’t love a teddy coat? In this outfit, a soft, camel-colored teddy coat is paired with a chunky cropped sweater and faux leather leggings. The mix of textures here is what makes this outfit a winner—the softness of the teddy contrasts perfectly with the sleek shine of the faux leather. Paired with white sneakers, this look is both playful and stylish, great for anything from casual shopping trips to coffee dates.
Adding a small cross-body bag keeps it practical and gives the whole outfit that easy, everyday appeal. For women cold weather 2024-2025 fashion, this is a must-try!
Inspiration for Styling Looks: This outfit channels the energy of fashion influencers like Camila Coelho, who often mixes cozy with glam. To recreate it, try experimenting with different textures—perhaps swap the faux leather leggings for velvet leggings or add a sequined bag for some sparkle. For a more everyday look, you could swap the cropped sweater for a longer one to create more coverage, while still keeping that fun, relaxed vibe.
Wide-Leg Pants & Knit Sweater Combo

Winter doesn’t always mean leggings and jeans! Wide-leg pants are having a big moment, and this outfit captures that perfectly. A light grey knit sweater tucked into navy blue wide-leg trousers, paired with classic white sneakers, is all about chic comfort. It’s minimalist yet elegant, great for business-casual settings or lunch dates.
For smart women looking for a comfy yet polished option for the colder months, this outfit is ideal. Add a structured tote bag to complete the look and you’re ready for anything—even if that just means another day of working from the local coffee shop.
Inspiration for Styling Looks: Olivia Palermo is known for her polished style, and this wide-leg pant and knit sweater combination is totally her vibe. To recreate this look, add a structured blazer for a more refined twist, or swap the sneakers for loafers if you’re heading into the office. If you want to make it more personal, try adding a statement belt or even layering some dainty necklaces to add interest to the knit sweater.
Long Coat & Scarf with Leggings & Slippers

Last but not least, we have a dreamy long white coat paired with leggings and comfy slipper boots. This look is all about warmth and comfort, especially with the cozy scarf that adds extra insulation against those cold winds. The soft color palette feels light and airy, a nice contrast to the often dark, heavy shades of winter wardrobes.
Perfect for weekend getaways or just enjoying a quiet walk in the snow. If you want to embrace women cold weather 2024-2025 trends, adding a long coat like this to your wardrobe is definitely the way to go.
Inspiration for Styling Looks: This cozy ensemble is similar to looks seen on Chrissy Teigen when she’s enjoying some downtime. To make it more formal, switch the slipper boots for knee-high leather boots and opt for a wool scarf in a rich color like burgundy. If you want to personalize it for everyday life, consider wearing printed leggings or adding a colorful tote bag for some extra character.
Cream Puffer Jacket with Wide-Leg Trousers

There’s nothing quite like staying warm in style, and this cream puffer jacket is doing just that. Paired with wide-leg cream trousers, matching gloves, and a scarf, this monochrome look is equal parts cozy and sophisticated. The soft, tonal palette is what really makes this outfit stand out—giving it an ultra-chic, cohesive feel. The Ugg-style slippers finish off the look, providing ultimate comfort for braving the snowy streets.
This outfit is perfect for women cold weather 2024-2025 who are looking for warmth without sacrificing an ounce of elegance. Bonus points for matching your coffee cup to your outfit—because it’s all in the details, right?
Inspiration for Styling Looks: This look resembles styles worn by influencers like Emma Hill, who loves neutral tones and minimalist fashion. To recreate this outfit for a casual day, add some chunky sneakers or swap the wide-leg trousers for fitted joggers. If you’re looking to personalize it, try adding a belt bag for a modern edge or a bold-colored beanie to break up the monochrome.
Black Coat with Blue Jeans & Combat Boots

You can never go wrong with a classic black coat during winter, especially when it’s styled with blue jeans and combat boots. This look strikes that perfect balance between edgy and refined. The high-neck black top gives off a sophisticated air, while the chunky combat boots add a bit of a rebellious twist. This is a great go-to look for women cold weather who are on the move and want to stay stylish while staying practical.
Pair it with a structured handbag to keep things looking polished, and you’ve got yourself a winter outfit that can easily transition from day to night. Women 2025 are all about balancing comfort and cool—this outfit nails it.
Inspiration for Styling Looks: Kaia Gerber is known for her effortlessly cool style, often seen in similar edgy combos. To make this look a bit dressier, swap the combat boots for heeled ankle boots and add some statement jewelry. Personalizing it could be as simple as switching the handbag for a cross-body or adding a beret for a Parisian twist—this outfit is versatile enough to work for different occasions.
Beige Wool Coat with Light Denim & Lace-Up Boots

A wool coat in a beautiful beige hue paired with light blue denim jeans and lace-up boots? Yes, please! This outfit is the ultimate in comfy street styles. The jeans add a relaxed touch, while the lace-up boots give it just the right amount of edge. The beige wool coat is both elegant and versatile, making it a must-have for women cold weather 2024-2025.
This look is great for running errands, catching up with friends, or simply strolling through the city. The muted color palette also makes it easy to accessorize, and the lace-up boots add that stylish practicality needed during winter.
Inspiration for Styling Looks: Jessica Alba often pairs wool coats with denim for an effortless, chic look. To recreate this style for a relaxed brunch, add a cross-body bag and some sunglasses. Want to make it more formal? Swap the denim for tailored trousers and add heeled boots. Personalizing this look is easy—try adding a colorful scarf or experimenting with different boot styles, such as chelsea or knee-high options.
Grey Sweatshirt, Long Coat & Beanie with Leggings

Looking to stay cozy but still want to maintain that casual-chic aesthetic? This outfit ticks all the boxes. A simple grey sweatshirt layered under a long, earthy-toned coat, paired with black leggings, comfy sneakers, and a beanie, makes for an easy yet stylish winter look. The beanie adds a playful touch, while the long coat keeps everything looking sleek.
This is a great women cold weather look for those casual weekends when you want to be warm but still look put together. Perfect for women over 40 who are looking for a trendy but practical outfit for chilly days.
Inspiration for Styling Looks: Think of this outfit as something similar to what Kendall Jenner might wear on a casual day. To recreate this look for different occasions, you could swap the sneakers for ankle boots for a slightly more polished vibe. Adding a chunky knit scarf or switching the beanie for a fedora is an easy way to personalize it. If you’re running errands, consider adding a roomy tote bag for practicality.
Oversized Scarf & White Wool Coat with Joggers

Who says you can’t wear joggers and still look chic? This winter look features an oversized white wool coat paired with cozy joggers, but the key piece here is the large, wrap-around scarf that gives off major comfort vibes. This outfit is perfect for those lazy winter days when you want to stay warm but still look effortlessly stylish. Paired with neutral-toned joggers and slipper boots, it’s the ideal balance of comfy and fashionable.
Want to stay extra warm? Add some mittens and a hot drink in hand. This outfit is the perfect definition of a women cold weather comfy yet elevated street style.
Inspiration for Styling Looks: Rosie Huntington-Whiteley often pairs oversized scarves with neutral tones to create chic yet relaxed looks. To recreate this look for a more formal setting, swap the joggers for high-waisted trousers and the slipper boots for heeled boots. To personalize, consider adding a colorful scarf or an embellished cross-body bag. You could also wear a patterned top under the coat to give the outfit some extra dimension.
Red Beanie, Grey Coat & Fur-Lined Winter Boots

Finally, we have a fun pop of color with a bright red beanie paired with a grey coat and dark denim jeans. The fur-lined winter boots add that much-needed warmth, while the striped sweater underneath brings some extra personality to the look. This outfit screams winter wonderland and is perfect for weekend adventures, whether you’re exploring a Christmas market or enjoying a snowy day out.
The comfy street styles feel of this outfit is perfect for those days you want to have some fun while staying cozy. Add a cross-body bag to keep things hands-free, and you’re good to go!
Inspiration for Styling Looks: This fun winter look is reminiscent of Reese Witherspoon’s casual style, often mixing practicality with color. To adapt it for a dressier event, swap the fur-lined boots for sleek knee-high leather boots. Adding a cross-body bag with a pop of color or switching to a patterned beanie can help you personalize it for everyday use. This outfit is all about having fun with winter accessories while staying warm.
Winter outfits don’t have to be boring or uncomfortable. Whether you’re all about oversized jackets, love a sleek coat, or can’t get enough of comfy leggings, there’s something out there that’ll make you feel like your best self. Which outfit idea did you love the most?
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