With winter comes cooler temperatures, shorter days, and the inevitable endless gloomy sky. This season can be restful and restorative, but it can also zap your energy – and sometimes all you want to do is throw on a casual outfit and call it a day. If your outfit brain hasn’t followed you into the new year yet, let me help by sharing some winter casual outfit ideas! From joggers to leggings (with a few chicer casual looks thrown in, because that’s just what I do), these outfits will help you figure out what to wear this week. Casual without being sloppy? Yes, please.
1. leggings + oversized sweater + tall boots + triangle scarf
leggings | boots | sweater | scarf
It doesn’t get much more casual than leggings and an oversized sweater, but if you want to elevate your at-home lounging outfit, slip on a pair of tall boots when heading out the door. Swapping out your slippers for a block heel adds a little something without making your outfit too dressy – no stilettos here!
Complete the look with a triangle scarf, which adds a cozy, winter-ready (and trendy) touch with minimal effort. If you live somewhere with colder winters, feel free to throw on your favorite wool coat.
2. joggers + hoodie + blazer coat + socks + loafers + tote bag
hoodie | jogger | coat | bag | loafers | socks
If you also pored over J.Crew catalogs because you loved the styling, this outfit is for you. A matching set is one of the easiest ways to look put-together – and who says a matching set can’t be athleisure? Your joggers and hoodie, usually reserved for travel, weekends, and sick days, can get a cute upgrade with just a few key pieces, like a stylish tote bag and classic loafers. For extra coziness and warmth, add a pair of cable-knit socks. The result? Stylish… and practical!
Finally, when you head out the door, throw on a peacoat or a blazer coat – like this one. It adds a polished touch to your outfit while keeping you warm. Now you’ve got your new favorite winter ensemble for bookstore and coffee shop runs!
3. corduory pants + white t-shirt + cableknit sweater + chelsea boots + beanie
tee | pants | beanie | sweater jacket | bag | boots
Corduroy, suede, cable knit – oh my! This winter casual outfit is all about cozy textures and layers, which are perfect for this time of year.
Start with corduroy pants, which strike the perfect balance between style and casual comfort. Pair them with a white t-shirt and a zip-up jacket to keep the look pulled together without feeling too dressy. Lug-sole Chelsea boots add casual style while giving you practical, sturdy support. A beanie ties the cozy, creamy tones together.
Even though the holidays are over, fair isle prints don’t have to disappear. Originally designed for islanders who needed warm, durable clothing to withstand harsh winters, this classic pattern is a perfect winter staple and can keep showing up in your winter casual outfits.
4. leggings + long sleeve shirt + vest + sneakers + tote bag
leggings | shirt | vest | sneakers | sunglasses | headband | bag
I know I love adding a chic touch to… well, everything (hence the website name), but here’s a tried-and-true really casual winter outfit formula.
Quality leggings and a long-sleeve tee create a simple base. The “statement” piece? A long puffer vest. It adds warmth, style, and extra bum coverage… bonus! Lean into the sporty-chic vibe with a fabric headband, chunky sneakers, sleek sunglasses, and a chic tote bag. Whether it’s school drop-off, a brisk walk with a friend, running errands, or your morning facial appointment, this casual outfit works for it all.
5. off-white jeans + long sleeve shirt + vest + boots
jeans | boots | vest | socks | shirt
Whether you’re taking a winter trip to the mountains or exploring Denver, this stylish yet rugged outfit is perfect for casual girls who have a hint of adventure. As previously mentioned, winter is the perfect season to lean into fair isle prints (like these socks) and embrace cozy textures like sherpa and faux fur.
Winter isn’t my favorite season—yet I live somewhere where it’s the majority of the year—but if there’s one good thing about this time of year, it’s the chance to snuggle up in soft, cozy fabrics. A high pile vest like this one pairs well over a fitted long sleeve shirt. The mix of creams and whites creates a soothing color palette that adds a calm, comforting presence to the season.
Want to add some color to this outfit? Take a cue from the socks. Icy or light blue is a trending winter color that instantly makes winter outfits feel a little bit fresher!
6. pull-on pants + hoodie + peacoat + baseball cap + tote bag + socks + loafers
pants | hoodie | baseball cap | peacoat | bag | socks | loafers
If your winter outfit inspiration is “city girl,” this is a perfect look for strolling the streets of New York -weather permitting, of course. For casual outfits, comfy pants like these drawstring ones are a must! They move with you as you go about your day, whether that’s working from home or exploring the city.
A Ralph Lauren hoodie adds a touch of preppy posh, though any hoodie or crewneck sweatshirt you already own works just as well. A baseball cap ups the casual factor – feel free to show some personality here!
I love the combo of loafers and socks, but a pair of sneakers would work well too. Complete the look with a shorter coat for that polished, effortless finish.
7. leggings + turtleneck + coat + triangle scarf + tall boots
leggings | turtleneck | boots | jacket | scarf | sunglasses | bag
If Audrey Hepburn were dressing for a light winter, this is what I imagine she would wear. Not everyone experiences frigid temperatures, and that’s where this outfit combo comes in. An all-black base nods to the winter season without being so heavy that you overheat.
If your climate is too warm for faux fur or wool coats, a twill jacket is a great alternative. This one adds a beautiful Parisian, vintage-inspired touch. To fully embrace Parisian chic, complete the look with a scarf and vintage sunglasses – designer bag optional!
Related: How to Recreate 15 of the Best Audrey Hepburn Outfits
8. sweater pants + white tee + sweater shell + slippers
pants | tee | sweater shell | slippers | glasses | watch | earrings
When it comes to building a casual, comfy winter outfit, I like to start with something stretchy. Leggings or drawstring pants work, but sweater pants? That’s what casual winter outfit dreams are made of!
Begin with a comfy base, then add layers for warmth and style. A white t-shirt is a wardrobe workhorse – and just because it has short sleeves doesn’t mean you can’t wear it in winter. Layering a sweater shell over it is a great option.
Sherpa-lined slippers or shoes take the cozy factor up a notch, while small accessories like a watch and earrings add a touch of style. This makes a perfect work-from-home outfit for your hybrid workdays.
9. sweater skirt + collar shirt + blazer coat + baseball cap + socks + loafers
skirt | sweater | baseball cap | coat | socks | loafers
Now, this final outfit may not look casual at first glance, but I had to include a true casual-chic option – and it’s comfier than you might think!
Made from the same cozy materials as sweater pants, this sweater skirt has all the makings of a wardrobe workhorse. Whether you want to style it casually or dress it up, it can do both. A collared sweater in merino wool is warm without the itch, making it a perfect winter option. A cute baseball cap adds a casual touch.
And yes, I’m still a fan of the loafer-and-sock combo, but socks with sneakers work too if you want a more relaxed vibe. Though the blazer adds a polished look, remember – it’s a blazer coat! If you need a winter coat, you might as well look stylish.
Winter Casual Outfits to Copy
Whether your idea of a winter casual outfit is leggings and sneakers or simply skipping the dress, there’s something here for everyone. The goal is to find pieces you actually enjoy wearing – something that makes the winter season a little more bearable – before we can start daydreaming about sunshine. Who am I kidding? I’m already looking forward to it!
But before it comes, let’s get inspired with 10 Everyday Winter Looks That Are Cozy, Cute, and Easy to Copy
I need I need a sharp chic comfortable outfit for an outdoor concert this summer(hot)for an older woman!!!lHelprose
Fun! Check out our summer posts for ideas 🙂