Everyday Winter Outfits I’ve Been Wearing (Casual, Cozy & Petite-Friendly)

If you’ve been around here for any length of time, you know I love cozy layers, earth tones, and fun accessories, so this outfit round-up is full of them!

Everything I’m wearing is linked under each photo, and I’ve added similar finds for anything that’s older or out of stock (it will be noted in the LTK description ). These are affiliate links, so I may earn a small commission—I appreciate your support so much!

This was a fun and different look for me! These boots are the comfiest heeled boots I’ve ever worn.

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Always up for a tonal look—I feel like it looks so put together and cool.

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Red on red—would be perfect for Valentine’s Day too!

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This outfit felt so fun! Definitely a vibe I’ll be trying to recreate!

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You can never go wrong with a cozy sherpa pullover, leggings, and slipper clogs.

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We had a “fancy dinner” at my parents and this is what I wore.

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Super comfy in a fleece zip up and comfy jeans.

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I’ve been loving cross-country skiing! It’s sooo good for my mental and physical health.

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Still living in this Walmart set! So comfy to throw on.

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Skinny/slim jeans are a great option for cold days!

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Always love adding that pop of fun color!

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Cozy days at home call for cozy outfits!

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Love a warm knit and a beanie to keep it casual.

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These are one of my favorite pairs of sweatpants. Such a cute wide leg fit.

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Loved the sporty feel of this outfit. So comfy too!

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A cozy sherpa and leggings!

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Winter walks in the woods are so good for me too!

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Outfits I’ve Loved Wearing So Far This Winter

I feel like I’ve found such a groove in getting dressed, in such a good way. I am loving the casual but put together feel that most of these outfits give off and I’m especially loving how they make me FEEL. There is nothing better than an outfit that makes you feel amazing and is still so comfy!

Here are 16 outfits I’ve worn over the last couple of months!

Everything I’m wearing is linked under each photo, and I’ve added similar finds for anything that’s older. These are affiliate links, so I may earn a small commission—thank you endlessly for supporting me, it truly means so much to me🧡

Loving this heavy green sweatshirt! The big buttons make it fun too!

Outfit linked HERE

I’ve been enjoying these comfy pants —I’m wearing the petite length and they come in regular length too!

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These pants are my favorite new item of 2025! I’ve loveddd wearing them! Perfect for dressing up or down!

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I think this sweater sold out (🥲) but maybe it’ll restock?! It’s such a cute one and I’ve received so many compliments on it!

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Corduroy and pop of red? Yes please!

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I just love puffer vest season! And I really love a fun colorful scarf too!

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Can you tell this sherpa has been on repeat (based on my last post too?😝)

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Jumped on the little triangle scarf trend (reminds me of the scarves I used to wear in college!) and I think it’s too cute.

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Been wearing this sweat set TO DEATH. So cozy!

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A crewneck is my favorite “I don’t wanna think about what to wear” outfit!

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This sweater is so fun with all the colorful Pom Pom pieces in it!

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Green on green forever— another puffer vest look!

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These barrel pants have been such a favorite for years. They’re so comfy!

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A printed sweater makes an easy cute outfit.

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Another pair of jeans I’ve been loving—a super comfy straight leg pair.

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Comfy cozy outfit!

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17 Everyday Winter Outfits for Real Life

Sometimes I think we over complicate style—especially in the winter.

Throw on a cozy sweater, or a base with an easy layer (vests, cardigans, and puffers forever), and a good pair of jeans and you’re good!Occasionally I throw on a skirt or leggings and that’s obviously super comfy too. All that matters is that I feel like “me” and enjoy what I’m wearing.

These are some recent outfits I actually wore— nothing really fancy, just super comfortable, warm, and easy.

You can find everything I’m wearing linked under each photo, plus similar options if an item is older. These are affiliate links, so I may earn a small commission—thank you endlessly for the support 🤍 it means more than you know!

Loved how my sweater matched my cowboy boots in this outfit!

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My striped turtleneck is a piece I’ve had for years. I love wearing it alone (like this) or layered with a sweater or cardigan over it.

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I love this cozy sherpa! Perfect paired with jeans, leggings or sweatpants.

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This colorful speckled sweater is so fun. It’s still neutral but the colorful pom poms make it extra cute!

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Definitely bringing my barrel jeans into winter with me. I paired them here with a cozy fleece sweatshirt jacket.

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I felt like the prettiest rainbow in this cardigan!

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These jeans are my favorite item of 2025! Love the length, comfort and look of them!

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There’s absolutely nothing wrong with a simple and cozy look like this!

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A cute crewneck sweatshirt is a favorite!

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This sweater has been such a favorite! I’ve worn it so many ways 🥰

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This fair isle sweatshirt is something I wear year after year. So cozy and oversized.

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Love pairing a cozy sweater with a mini skirt (or in this case, a skort!)

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This coral color is so pretty. It’s so fun to pair with printed matching socks.

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Another outfit with this cozy Sherpa pullover! Love it with my brown leggings.

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We went to a hockey game and I wore the team’s colors (green and gold).

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Another way I’ve worn this sweater—paired with my barrel jeans and uggs!

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A cozy outfit! Love these wide leg sweatpants and a cozy fleece jacket.

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10 Layered Looks for Cold Winter Days

Here are some of my most recent outfits! As always, there is lots of layering, fun colors, textures, and a mix of comfy and put together.

Where I live in Northern NY, winter is long. You’ll be seeing me wear layers and cozy items for a good long time until spring decides to show up.

Under each photo, you’ll find links to the featured pieces or similar options if the originals are no longer available, all through LTK. These are affiliate links, which means I may earn a small commission if you decide to purchase—at no additional cost to you. I truly appreciate your support!

This flannel is older, but I loved pairing it with these favorite jeans (on sale for $39.99 right now!) and my black leather Chelsea boots.

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This crewneck look gives me casual/cool vibes and was super comfy!

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Threw this on for a quick trip into town to grab something to eat! Love a grey sweatpants look.

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A puffer vest is such a staple for me and I love it paired with a cozy oversized sweater and cute boots (these ones are actually rubber rain boots but don’t look it and are SO comfy!)

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These corduroy wide leg pants have QUICKLY become a favorite for me! They’re a mix between a brown and a green and definitely petite-friendly.

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A Henley top is always cute and I love this brown one paired with my free people utility jeans.

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Colorful and cute! Again, wearing those cute rubber boots!

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Loving this lime green sweater and matching my hat to my blundstone boots! I threw on this packable puffer for a cute monochromatic moment.

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I own these wide leg sweatpants in multiple colors now and loveee them!

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This coat is amazing for cold winter walks!

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