Cold weather can come at any time of the year. Whether it’s a chilly evening in the spring or a blustery, cold night in the winter, dressing in layers is best when cold weather is expected. However, layers can sometimes feel like a challenge when it comes to showing off your personal style. It’s all about investing in the right pieces. Today, I’m sharing a round-up of 20 cute cold weather outfits to wear to a variety of places and events.

20 Cute Cold Weather Outfits

Slim Straight Pants with a Cashmere Sweater

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The first four outfits featured in this cute cold weather outfit roundup are great cold weather office outfits. A white button-down top is a great staple to have in your winter wardrobe because you can easily layer it underneath a sweater. This provides more layers for your look to keep you warm. I paired this combination with slim straight workwear pants and a pair of slingback cap-toe heels.

You can watch my most recent workwear try-on here on YouTube.

Straight Leg Pants with a Blazer

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The best thing about a blazer is that they are fitting year-round. However, they’re the best in the winter because they give you an effortless layer to keep you warm during cold weather, and also give you that chic look for the office. Layer a simple blouse underneath the blazer. You can opt for a neutral color, like this blush pink option I have on. You can also add a bright color to give this cute winter outfit a pop of color.

Straight Leg Pants with a Fitted Turtleneck

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This monochromatic look creates the perfect business casual outfit for the winter. I added a leather belt to break up the look and add a little sophistication. This ruffle neck ribbed top is the perfect addition to your winter wardrobe because it can be styled in several different ways for the season. These slim-cropped pants are also made of a stretchy material, making them great for staying comfortable on long workdays.

wrap jacket with faux leather leggings

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This is one of my favorite cozy pieces in my wardrobe! I’ve had this wrap jacket for a long time now, and I wear it frequently. I love to pair this jacket with another staple winter wardrobe piece of mine, these faux leather leggings. Top off this comfortable look with ultra mini UGGs and call it a day!

Cardigan and Moto Jacket Over a Fitted Top

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These next two outfit ideas are cold weather church outfits. The first look layers a cardigan over a neutral top. I paired the Spanx perfect pant with flats to complete the look. The pants are one of my favorites to dress up or down, and they are incredibly comfortable. You could also wear a knee-high boot with this look.

The second outfit is a bit more dressy. It’s styled with the wide-leg pants by Spanx. These elongate your legs and pair well with neutral pumps. I added a faux leather moto jacket for an edgier look. The bodysuit and moto jacket would also look great paired with flare jeans.

Tunic Top with Black Skinny Pants

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Brunch is always a good idea, especially when it involves avocado toast. This next round-up for four looks are cute outfits to wear to brunch. This effortless look pairs a tunic-style top with skinny black pants. A tunic top is the ideal silhouette to pair with skinny jeans or leggings. This one has a beautiful pearl button to elevate the look.

Flare Pants with a Cardigan or Blazer

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These next two outfit ideas could be worn to several places. Wear them to church with brunch afterward or to the office. These cold weather brunch outfits have versatile pieces to mix and match with other items you probably already have in your closet.

The lady jacket gives the first look some texture and structure. I have the outfit styled with pumps, but a pointed-toe ankle boot would work just as well.

The second look layers the button-down white shirt with a beautiful cardigan. I left some of the white shirt peeking out at the cuff. It elevates the look a bit more.

Flare pants with a Moto Jacket and booties

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Go brunchin’ in style with these flare pants. I layered a moto jacket over the top. Then, I paired neutral covered-heel booties to complete this cold weather outfit.

Tunic sweater with leggings and knee-high boots

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One of the best go-to outfits in the winter that never fails is an oversized tunic sweater paired with leggings. You can easily dress up this look with leather knee-high boots, a large cozy scarf, and even a headband with a bow to top it off.

Slip Skirt with a Cashmere Sweater

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This next couple of looks are cold weather date outfit ideas. I also recently did an entire post dedicated to date night looks for the winter here.

When thinking about what to wear on your next date night, you first want to determine where you’re headed. If it’s a casual place, opt for jeans. If it’s more upscale, the above look would be a great date night option. Pair a slip skirt with a cashmere sweater and knee-high suede boots for a warm, yet flirty look.

Lace Top with Skinny Jeans

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A more casual date night option is this date night outfit. I paired a lace top with skinny jeans. Though jeans are more casual, the lace adds a bit of elegance to the overall look. Pair a rich espresso knee-high boot and coordinating leather belt to complete the look.

fuzzy coat with straight-leg jeans

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This coat is so warm and cozy, making it the perfect addition to your winter wardrobe! To keep it simple but still sophisticated, I paired this coat with a white long-sleeve turtleneck bodysuit, straight-leg jeans, and boots. This outfit is a great fit for several different winter occasions, such as a casual date night out, a girls night out to dinner, or something that involves and outdoor winter activity.

Midi Sweater Dress with Pumps or Boots

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I wear a sweater dress any chance I get in the winter. These two would be fun to wear to a birthday celebration, too. Notice both pumps and boots pair well with a midi-length sweater dress.

cropped Faux Fur Jacket with straight-leg Jeans

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Music festivals are fun to go to with a group of friends. But if the weather isn’t in the 70s or 80s, what should you wear?

A cropped faux fur coat is a great place to start. Then, you can build your look around that. This turtleneck bodysuit layers beautifully underneath this faux fur coat, and won’t take away from it. Straight-leg jeans are a trendy jean silhouette and are flattering on anyone. To complete the look, I paired it with black boots.

button-up cardigan with straight-leg jeans and flats

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For a classic and refined winter look, try pairing a button-up cardigan sweater with a turtleneck bodysuit, straight-leg jeans, and flats. This particular sweater has pearl buttons which I adore. This is a look that can be recreated over and over again with different sweaters, jeans, and flats. I also added a hair bow to elevate the look.

Maxi Dress with Booties

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Last, but certainly not least, is a look that I love to reach for and recreate all winter long. I started this look with this cashmere turtleneck sweater and paired it with skinny jeans that tuck nicely into a pair of knee-high leather boots. I also added this thick, warm scarf for an added layer of warmth on extra chill days. This look is timeless, and one that will be in style for many winter seasons to come!

What’s your favorite cold weather winter outfit in this round-up? Let me know in the comments below!