Winter is here, and while that means cozy nights and holiday vibes, it also comes with the daily challenge of getting dressed. Putting together cute winter outfits that are actually warm can feel tricky, but I promise—you don’t have to choose between staying cozy and looking stylish.
In this post, I’m sharing 34+ winter outfit ideas—from casual looks you’ll love for everyday errands to chic winter outfits that work for dinners, date nights, and holiday parties. Think cozy knits, polished boots, and effortless layering formulas you can easily make your own.
Here’s what you’ll learn:
✅ Easy layering tips to create cozy winter outfits that actually keep you warm
✅ Outfit ideas for every occasion—from coffee runs to winter date night outfits
✅ Shopping picks and styling tips to create trendy winter outfits you’ll actually want to wear on repeat
Let’s dive in ⛄️
Layering Essentials for Cozy Winter Looks:
When it comes to putting a winter outfit together, layering is the secret! I’m going to take you through my layering essentials that I cannot go without in the winter. These essentials help me come up with endless winter looks.
Trust me, I am a hot weather creature. It was key for me to stay extremely warm during winter in Chicago in order to survive 😂 So these cute winter looks are also SO COZY!
So, let’s talk about layering!
🧣 Layering With Scarves:
Scarves are one of the easiest ways to turn simple layers into cute winter outfits. Not only do they keep you cozy, but they instantly add color, texture, and personality to your look.
Go for a chunky knit scarf when you need maximum warmth, try a bold pattern to make casual winter outfits pop, or choose a lightweight wrap for those milder winter days.
A good scarf can pull your whole look together while keeping you snug all season long.
⭐️ My favorite places to shop for cozy winter scarves:
- A Mongolian cashmere wrap like this one will keep you super warm and chic (it’s not as expensive as it sounds!)
- For cute prints and cozy blanket scarves check out this link. (all under $100)
- All of Quince’s scarfs and pashminas, here.
Layering With Cardigans and Vests:
When it comes to layering, nothing beats a cozy cardigan or a sweater vest. These pieces are true winter staples—you can throw them over just about anything and instantly create stylish winter outfits that feel warm and effortless.
Long cardigans are perfect for layering over jeans, skirts, or even dresses, while vests add an extra layer of texture and dimension to casual winter outfits. The best part? They never go out of style, so you’ll reach for them year after year.
👉🏻 Also read: how to pick the right sweaters for your body type!
⭐️ My favorite places to shop for long cardigans & vests:
- My favorite long cardigans here.
- Regular length cardigans here.
- Cutest and trendiest vests for the season here.
- A favorite sustainable sweater store if you’re not on a tight budget here.
- Want something different and unique? Check out this page at Farm Rio 😍
Does your closet pass this test?
If you’re reading my blog, it’s probably because you also like to maximize everything you already have in your closet right?
Well, you can find out the health of your closet by answering these 7 questions! And no worries, I’ll tell you what to do next based on your results. Get started ⬇️
Styling The Versatile Winter Tights!
Tights are an absolute must for my winter wardrobe, and with good reason! They’re comfortable and warm, but also can be worn in so many different ways.
You can turn a lot of the pieces you wear the rest of the year (like shorts, skirts and dresses) into a cute winter outfit thanks to tights (and a sweater).
👉🏻 Also read: the fall and winter fabrics that will make layering so much easier!
Classic Winter Outfits With Tights:
Tights are the secret weapon for building cute and warm winter outfits. The classic combo—an oversized sweater or tunic with tights and boots—never fails, but that’s just the beginning.
Layer them under shorts, skirts, or dresses to instantly turn warm-weather pieces into stylish winter outfits you can wear even when it’s freezing outside. It’s an easy way to multiply your options and create endless trendy winter outfitswithout sacrificing comfort.
Tights Under Shorts, Skirts, or Dresses:
The reason why you should have a good pair of winter tights in your closet is that it can extend the life of your shorts, skirts, and dresses into the winter.
You will have so many more options for coming up with outfits even if it’s freezing outside.
Check out these layered legging outfits below for some inspiration ⬇️
⭐️ The best and coziest winter tights:
- I recommend that you invest in a couple of good quality winter tights. You will wear them often, so want them to stay in top shape. Browse some good options here.
- This one is a great option for the less cold winter days.
Footwear Options to Complete Your Cute Winter Outfits!
Choosing the right footwear in the winter can be a balancing act. I always consider the occasion and weather, and opt for what makes the most sense. Sometimes you’ll choose style over practicality, but when it’s a more casual outing and the weather is well, frightful… you’re going to opt for your more weather-proof options!
I used to think I always had to wear the coziest winter shoes… but there’s a very important thing you have to consider when picking which winter shoes to wear… are you walking or driving?
Often times we took Ubers everywhere! That’s when I went for the most stylish options – sometimes that even meant white leather sneakers! (that’s when I was OVER winter shoes towards the end of the season lol)
Winter Outfits With Rain Boots:
Rain boots don’t have to be boring! I love my red pair to add a pop of color, but there are so many styles and options out there to express your own personal style.
Winter Looks With Over-the-Knee Boots:
This is a dressier option that pairs well with skirts, dresses, or jeans! A tall boot looks chic, but also covers a lot of leg so you get the added benefit of extra warmth when needed.
Cute Winter Outfits With Snow Boots:
A good pair of boots for those extra snowy days is something you’ll want to invest in if you live in a climate where things can get icy!
I love the pair I own because they marry comfort, function and style and work seamlessly with so many outfits.
Winter Outfits With Ankle Boots:
I love a good pair of ankle boots because they can be dressy or casual. I suggest a neutral pair in your wardrobe because they work with endless outfits.
But if you like to add a pop of color, your footwear is a great way to do that too!
⭐️ My favorite places to shop for different styles of winter boots:
- The best and most durable rain boots
- Cute OTK boots for every style
- Stylish and cozy snow boots
- Cute, sustainable and affordable ankle boots
- My favorite booties from Nordstrom
Accessorizing with Winter Hats or Beanies:
Winter hats are for more than just warmth! They also can add some flair to your outfit and tie the whole look together. I love styling a wool hat or a cozy beanie in the wintertime for a fashion-forward accent that also adds warmth.
It’s all about being warm!
Winter Outfit Ideas With Wool Hats:
Cute Winter Outfit Ideas with Beanies:
⭐️ My favorite places to shop for cute winter hats:
Cute Winter Outfits for Dressier Occasions:
Not every winter look has to be casual—sometimes you need something a little more polished. Between holiday parties, dinners with friends, and the occasional winter date night outfit, it’s worth having a few dressier options ready to go.
⭐️ The good news? Chic winter outfits can still be cozy. Think sleek boots with a sweater dress, tailored trousers with a statement coat, or a silk midi skirt layered with a nice cashmere sweater and tights.
These dressy looks strike the perfect balance between warmth and style, so you never have to sacrifice comfort when the occasion calls for something special.
Final thoughts about creating cute *and warm* winter outfits:
I hope these ideas gave you plenty of inspiration to try new cute winter outfits this season. From cozy layers to chic dressy looks, winter style is all about mixing warmth with personality—and the right pieces make it so much easier.
Remember: layering is your best friend, accessories can completely change a look, and investing in a few key staples will give you endless stylish winter outfits to wear on repeat.
What’s your go-to formula for a warm winter outfit? Drop it in the comments—I’d love to hear!
Thanks so much for reading 💜
XO,
Aimara
PS: does your closet need a little purge? Take the FREE closet score quiz here! It will help you assess the state of your closet and I’ll let you know how to fix it and what to do next. Let’s maximize that wardrobe of yours!
About The Author:
Hi, my name is Aimara and I am the voice behind Ways of Style. I was born and raised in Venezuela until the age of 27 when I moved to Chicago, and 2 years later I met my best friend and husband. We now travel full time and live out of a carry-on bag, so believe me, I know a thing or two about how to maximize every single piece I own.
I love creating new looks, and looking cute while I’m traveling. And in this blog, I try to share all my outfits, even if I don’t have the best photos ;) My goal is to help you maximize every piece you have in your closet and to encourage you to live with less things.
Related style posts you would like:
- How to create stylish monochromatic outfits
- How to style one striped sweater in 6 different ways!
- How to create a fall capsule wardrobe without black
- How to wear a long cardigan
- How to build your first capsule wardrobe with just 30 pieces
Did you feel inspired with these 34 cute winter outfits? Share it on Pinterest!
Leave a Reply