Winter is here and sometimes that means that creating a cute (and warm) outfit can be a daunting task! But don’t worry, I’m here to make it easy for you. Just because it’s cold outside doesn’t mean you have to sacrifice style! You really don’t.
Today I will be sharing over 34 cute winter outfit ideas that are versatile, cozy, stylish and easy to replicate with items you probably already have in your closet. My goal is to inspire you to create your own version of any of these winter looks!
These outfits are perfect for everything, from a casual brunch with friends to slightly more dressy occasions, like date night or dinner parties.
So let’s dive into some stylish winter outfit ideas and of course, styling tips to inspire you to dig into your closet and come up with some creative new outfit ideas to rock this winter season ⛄️
Layering Essentials for a Cozy Winter Look
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 can add warmth and flair to any outfit! Check out how I wore mine below
You can layer your outfits with a chunky knit, patterned, or even a more lightweight scarf for milder winter climates.
⭐️ 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)
Layering With Cardigans and Vests:
Another go-to for me in the winter? A cozy long cardigan or vest!
Long cardigans and vests are absolute closet staples, and I love that through the years they really never go out of style. They pair well with everything, from casual jeans to skirts and dresses.
👉🏻 Also read: “How to wear a long cardigan” AND “How to style an oversized sweater” for more cute Winter outfit ideas!
Check out some ways I have styled my vests and long cardigans for the colder months below!
⭐️ My favorite places to shop for long cardigans & vests:
- This store has the dreamiest fabrics at very affordable prices!
- 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 😍
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).
You know I’m all about maximizing everything inside my closet.
If a lot of the bottom pieces I’m wearing below look familiar, it’s because I also style them the rest of the year! You can see them all over my other blog posts for different seasons.
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 ⬇️
Classic Winter Outfits With Tights:
The obvious way to wear tights is on their own with a cozy oversized sweater or tunic and your choice of winter footwear! Yes, this look never fails!
But there are also a gazillion ways to style winter tights… so let’s take a look at those, shall we?
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. I always had these ones, and not only were they super flattering, they stayed in great shape for many winters!
- 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)
So, without further ado, these are the boots in my winter shoe wardrobe:
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 (you only need one pair)
Accessorizing with Winter Hats
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!
Last but not least, let’s talk about creating dressy and cute winter outfits!
Winter comes with its fair share of occasions where you have to dress up a little. Between the holidays, getting together with friends, and the occasional date night—having a few outfits to dress up is key!
Here are some outfits that are on the dressier side, but are still cozy and warm:
Final thoughts about creating cute *and warm* winter outfits:
I hope these outfits inspired you to create some cute and cozy winter outfits this season! When it comes to getting the most mileage out of your closet this winter, don’t be afraid to mix and match.
Layering is your friend, and can even help you extend the life of your warmer weather wardrobe pieces well into the colder months!
Let me know what your go-to winter outfit combination or closet staple is below in the comments!
Thanks so much for reading. Remember I’m always here if you have any questions 💜
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 find your personal style?
- Everything you need to know about outfit formulas!
- How to build a minimalist wardrobe
- 10 timeless ways to style a leather skirt
- 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