January 17, 2022 — Casual
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.
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.
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.
4. Puffer Coat Over Leggings
Mix functional athleisure pieces, like my Lululemon puffer and beanie, with casual base layers for an all-black look.
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.
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. 🙂
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.
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.
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.
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.
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.
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).
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 a casual Friday at the office, a night out, or a day-to-night look.
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.
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.
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).
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
