16 Cute Cold Weather Outfits that are Actually Warm

blogger wearing cute cold weather outfit with black bodysuit black mini skirt commando tights and over the knee boots

Getting dressed for winter weather often means wearing as many layers as possible—which can lead to looking bulky rather than stylish. Thankfully, with a few tips, it’s possible to create cute cold weather outfits that are not only sleek but will keep you warm for whatever weather is on the horizon! In this post, I’m sharing 16 winter outfits that are stylish and cozy, plus tips for creating your own looks when it’s freezing out.

Casual Cold Weather Outfits

Casual winter looks are always the crowd favorite. Here are eight comfy and warm winter looks that are perfect for running errands around town, casual Friday at the office, or tailgating on a cold game day.

1. Shearling Coat Over Winter Whites

Style winter whites as your base layer, then add interest with a shearling coat. White sneakers work well if you’re wanting an ultra-casual ensemble, or go classy casual with white boots.

shearling jacket with white jeans and white boots

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2. Blazer Coat with a Hoodie

The first example of a cozy winter outfit featuring faux leather leggings in this post (you’ll see why I call them a winter staple!). Dress down a blazer with a hoodie and moto boots, then grab a backpack or a crossbody for venturing around town while keeping warm.

wool blazer coat with white hoodie faux leather leggings stuart weitzman kolbie boots

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3. Faux Fur Vest with Denim

A vest is a great way to dip your toes into the world of faux fur. Balance the dressy vibe of the vest with laid black denim and boots.

black faux fur vest with black turtleneck frame le skinny de jeanne jeans and stuart weitzman kolbie boots

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4. Puffer Coat Over Leggings

Mix functional athleisure pieces, like my Lululemon puffer and beanie, with casual base layers for an all-black look.

blogger wearing cold weather outfit with black puffer coat faux leather leggings combat boots and black turtleneck

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5. Camel Coat Over Athleisure

During the week, athleisure is admittedly the base of almost all of my comfy casual winter looks—I add polish with a chic wrap coat over top.

cute and casual cold weather outfit with camel coat and sneakers

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6. Puffer Coat with Faux Leather Leggings

The puffer featured below is 100% animal free. And there we go again with the faux leather leggings. 🙂

casual puffer coat outfit for cold weather

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7. Puffer Jacket with Waterproof Boots

A short puffer jacket, waterproof boots, and a cashmere sweater is great for days when there’s winter weather in the forecast.

casual puffer jacket outfit for cold weather

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8. Oversized Sweater with an Overcoat

This sneaker look is ideal for walking to class, working from a coffee shop, or the weekend. I love my Veja Sneakers and have a full Veja review if you want to learn more about the brand.

casual winter outfit with white coat black jeans and veja sneakers

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Dressy Cold Weather Outfits

Here are eight dressy outfits for cold weather, including ideas for holiday looks, winter date nights, a night out with friends, and the office.

1. Faux Fur or Teddy Coat with Pants and Heels

I love this look for when I’m wanting to feel extra toasty. Layer a faux fur, shearling, or teddy coat over fitted base layers, like pants or jeans and a crewneck sweater.

woman wearing cute cold weather outfit with faux fur coat and faux leather pants

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2. Cashmere Sweater Dress with OTK Boots

This is one of my favorite cold weather outfits because it transitions seamlessly from mild fall temps into true winter weather. OTK boots keep the legs warm, a turtleneck dress keeps the upper body covered, and a coat adds a finishing touch. You could layer skin-toned or black tights underneath for added warmth.

woman wearing dressy cold weather outfit with black sweater dress wool coat and thigh high boots

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3. Belted Slip Skirt with a Turtleneck

You’ve probably seen slip skirts styled with a sweater and a belt in street style photos on Pinterest and elsewhere; the belt helps create a waist without taking away from the cozy look of the sweater. Layer a coordinating wool coat, then add tights and a fitted cami underneath if you need them.

dressy cute cold weather outfit with black skirt white turtleneck belt and wool coat

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4. Leather Mini Skirt with Tights

To stay warm while bearing your stems in a mini, reach for high-quality tights. Try over the knee boots or knee high boots and choose the option that feels best with the proportions of the skirt (my *general* rule is the longer the skirt, the shorter I want my boots to be for balance).

dressy outfit for cold weather with wool coat black mini skirt commando tights black turtleneck and black thigh high boots

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5. Dressy Winter Outfit with Jeans

Going tone on tone with a sweater and a coat looks so chic with contrasting denim on the bottom. Try this look for casual Friday at the office, a night out, or a day to night look.

dressy cute cold weather outfit with white coat and jeans

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6. Sweater Dress with Heeled Boots

I love a midi sweater dress that covers the legs because it’s so easy to style. Paired with stiletto booties and a camel coat, this is perfect for date night or any dressy winter occasion.

dressy winter outfit with camel coat black sweater dress heeled booties

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7. Dressy Sweater and Faux Leather Pants

Dress up coated or faux leather pants with a fitted sweater, heels, and a leather jacket for an on-trend, slightly edgy look.

black coated pants outfit for winter with white leather jacket and black heels

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8. Winter White Outfit

This dressy winter outfit combo is perfect for holiday events or a special occasion. Layer an ankle-length wool coat (I’d go with camel or white here).

dressy cute cold weather outfit with white skirt and white turtleneck

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How to Look Cute and Dress for Cold Weather

Mastering layering your winter clothes so that you feel warm and don’t look bulky just takes a little practice. Here’s how I’ve learned to put together cute cold weather outfits that are chic and adaptable for freezing temperatures:

1. Layer Strategically

The golden rule of layering is that each layer should work on its own. Your base layers should fit close to your body. For example, if you work in a heated office but have a chilly commute, you’ll want the look to feel complete once your top two layers are removed.

2. Three Layers Max

I’ve found that three is the magic number for layering. Any more layers can cause you to look bulky or (worse!) make it difficult to move around.

3. Wear the Thickest Layer on Top

I always try to think “thin inside, thick outside,” when it comes to ordering layers. Bulkier items like faux fur, down, puffer jackets and parkas, and shearling go on top. Thin materials like cotton, pima, and merino wool work well in base layers.

4. Pay Attention to Extremities

Hands, head, and feet are the first to lose heat, so I take special care to keep them covered. Tights will be your best friend underneath dresses and skirts, and knee high and thigh high boots help cover the legs. If it’s especially cold, I try to have thin merino wool socks, touchscreen gloves, and a cashmere beanie on hand.

5. Invest in Quality Outerwear

Even though we don’t live in a climate where we experience winter weather regularly, having high-quality winter coats and jackets on hand that keep all the elements out is something I’m always grateful for! They also come in handy for our ski trips. Wool, fleece, down, and nylon are great insulators. Mackage and Reiss make gorgeous wool coats, and Woolrich, Moncler, Mackage, and Save the Duck make beautiful tailored puffer coats.

What to Wear in Really Cold Weather

I will admit that there’s definitely a temperature and a type of weather (wind, sleet, etc.) when looking cute becomes an afterthought as you’re trying to prevent your body from turning into a full-blown icicle. 🙂 Even so, a few practical base layers can keep you warm without adding too much bulk. When we visit Montana where the temps can get in the negatives, this is what I bring:

  • Mittens or touchscreen gloves
  • Merino wool socks
  • A scarf that can cover the mouth
  • Waterproof winter boots
  • Water-resistant coat

Cute Cold Weather Outfit Staples