As much as I love a theme or an excuse to get all dressed up, the truth is that I always feel most at home in casual, everyday looks – especially in the wintertime. Nothing beats reaching for a soft sweater and getting wrapped up in a warm wool coat when it’s freezing outside. And those of us in the Midwest? I’d like to think that many of us have mastered everyday winter looks that are just as cute as they are cozy. Subzero temps are no joke, but we make the most of it. And if you’re looking for ideas to style your favorite winter wardrobe pieces this season, you’re in the right place for inspiration! Keep reading for 10 cold weather looks for cute casual winter outfits.
1. Holiday Errands
boots | jeans | coat | sweater | hat | bag
When you’re dealing with the holiday crowds and the sun setting as soon as 4 pm hits, sometimes a little serotonin boost is in order! I love incorporating a bright pop of color into cute winter outfits to make myself feel a little more awake and vibrant, even if it’s cold and gloomy outside.
A colorful sweater goes a long way in making your winter neutrals feel fresh again for a new season. When you’re going for a more casual aesthetic, a bold striped sweater adds a little bit of playfulness to your go-to jeans, boots, and wool coat combo. And don’t be afraid to have a little fun with your accessories either – a pom hat is always a fun way to do this!
2. Grabbing Hot Chocolate
boots | pants | bag | coat | earrings
Sometimes warming up involves trekking outside in the cold, and if you’re headed out into the tundra to grab a steaming cup of hot cocoa this winter, you can look cute and cozy in a few winter classics. First, a scarf coat might just be one of the most elegant trends to pop up in winter fashion over the past few years. Not only is it two pieces in one, but the coordinating colors instantly make you look more put-together and polished, even if you’re pairing it with leggings and Uggs.
And speaking of coordinating, try sticking to one or two colors if you’re going for the cohesive, polished look. Camel and black is our chosen color combo, so stick to a camel brown bag, shoes, and gold earrings to finish off your look!
3. Christmas Tree Farm
boots | leggings | bag | coat | sweatshirt | hat
This time of year (between Halloween and New Year’s), there’s no shortage of fun, festive activities to fill up your weekends. From sleigh rides to winter concerts to holiday shopping, you’ll have plenty of opportunities to style cute casual winter outfits over the next couple of months. The trick is to balance warmth with classic winter essentials!
For a trip to the Christmas tree farm, think functional, yet photo-ready. (After all, isn’t this one of the best photo ops during the holiday season?) I certainly can’t resist it! To get that perfectly cute yet casual look, start with a few easy basics like leggings and a sweatshirt. They’re comfortable to hike around in, and can still look chic when paired with a more elevated wool coat and knee-high boots. Add a coordinating hat and a sleek leather bag to polish off your look, and get ready to pose (and find the perfect tree, of course).
4. Holiday Movie Marathon
slippers | sweatpants | sweater | t-shirt | earrings
While you cozy up watching the Harry Potter series, Christmas with the Kranks, or The Holiday (a few of my own favorites) this year, comfort is #1 in finding the ideal outfit for your holiday movie watching marathon. I always like to reach for monochromatic looks when I’m planning a lazy day at home. The look of a matching set makes me feel a little more put together, but I can still go for my favorite sweats and cozy sweater.
To add a little bit of dimension to my look, I layer a white t-shirt underneath my sweaters. This is also a great strategy if you like to wear materials like wool or cashmere, but are a little bit skin-sensitive. Add a pair of shearling slippers and pearl earrings to feel just that much more polished, even while you’re curled up on the couch.
5. Weekend Getaway
boots | jeans | bag | sweater | coat | earrings
The après-ski look is the perfect inspiration for winter outfit ideas. Whether you love to ski or maybe just find yourself dreaming about curling up with a book in front of a big fireplace in a cozy lodge somewhere, this aesthetic offers plenty of cold-weather staples to influence your casual looks. Think warm boots, Fair Isle sweaters, fur details, and sleek puffer coats.
Whether you’re headed to a ski resort or somewhere else for a little weekend getaway, let apres-ski style inspire your dream winter casual look. Pair a Fair Isle sweater with dark-wash jeans, a puffer coat and a Longchamp Le Pliage travel bag to weekend in style!
6. Window Shopping
boots | jeans | bag | coat | shirt | scarf | sunglasses
The holiday season might just be the very best time to window shop! I love heading into the city during the holidays to take a look at all of the wild window displays, decked out in Christmas decorations and different themes. It makes every street look a little bit brighter, and the stores seem to glow from within. Even if you aren’t out to do any actual purchasing, the holiday mood is infectious just walking up and down a busy shopping street during the holidays.
If you’re going for that effortlessly cool, city girl vibe, reach for a classic wool coat from your winter wardrobe. Because this is often an investment piece for your winter capsule wardrobe, I always recommend going for a neutral color! Neutral, black, navy, or camel are great examples. And as for the rest of your look, keep it casual with a tan scarf, white long-sleeved tee, denim, and a pair of comfortable black boots.
7. Winter Brunch Date
boots | jeans | bag | sweater | coat | scarf | earrings
If your idea of casual looks for winter tends to lean a little more on the chic side of casual chic, try swapping out your classic denim for your white jeans! Yes, you can wear white after Labor Day with the right styling. On top, reach for a cozy turtleneck to help balance out the light denim. A brown coat helps to tie both pieces together! Add a few more winter details like a calf-hair tote in leopard print, a triangle scarf, and ankle boots, and you’ve now successfully transitioned your white jeans from warm to cold weather.
8. Holiday Travel
boots | socks | jeans | bag | sweater | jacket | earrings
Holiday travel might not be everyone’s favorite part of the festive season, but one easy way to make it a little more enjoyable? Pick out a cute outfit that makes you feel confident and comfortable! Whether you’re traveling by plane, train, or automobile this holiday season, a good outfit always makes everything a little bit better.
Light layers are key to the perfect travel outfit, even in the wintertime. A light coat, a thin turtleneck, and one of your favorite pairs of jeans make for a winning formula. Add a pair of leather boots, some knee-high socks, and simple jewelry for a chic, minimalist look for your busy travel day.
9. Winter Farmer’s Market
shoes | leggings | bag | shirt | jacket | hat
Just because the vendors head indoors doesn’t mean you have to stop frequenting your local farmer’s market! Many cities offer a winter version of your favorite summer activity; you just have to find their cold-weather location. It’s the perfect opportunity to stock up on homemade jams, pastries, and bread – all of which make great hostess gifts when you’re heading to your next holiday party.
Of course, your favorite farmer’s market outfit probably isn’t fitting for the winter market. You’ll still want a casual outfit, but something that’s a little bit warmer than your go-to linen and cotton pieces. Instead, try a shearling jacket, leggings, and burgundy accessories (like coordinating sneakers and a baseball cap) for an effortlessly chic look that still feels laidback enough for an early Saturday morning.
10. Holiday Decorating
slippers | socks | pants | sweater | shirt | hat
If your ideal winter season involves leaving the house as little as possible, you probably treasure the game nights, movie marathons, and cookie baking that keep you cozy and indoors through the coldest months of the year. Holiday decorating might also be one of your favorite ways to celebrate the festive season!
And if you want to style a cute outfit (even if you’re not leaving the house), try pulling a few pieces from your French-inspired capsule wardrobe. A striped t-shirt, half-zip sweater, and cozy sweater pants in a neutral color all complement each other, but still feel like more than loungewear.
Cute Casual Winter Outfits for All Season Long
Whether you’re the type to spend all winter on the slopes or prefer to stay snuggled up with a book in front of the fireplace at home, you don’t have to give up your dream chic style to stay cozy. These two can go hand in hand with the right outfit ideas this winter, and now you have 10 ideas to help you get started!
Feel like your winter wardrobe needs a little bit of updating for the season? Up Next: 11 Winter Outfit Staples Your Wardrobe Might Be Missing
