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. Many of these workwear pieces are from Spanx. They think of every little detail a woman needs in pieces. For example, this white button down layered underneath this cashmere sweater has stitches in between the buttons. That way, there’s no gapping when you move or sit.

A white button down is a great staple to have in your winter wardrobe because you can easily layer it underneath sweaters. This provides more layers for your look to keep you warm. You can watch my most recent workwear try-on HERE over on YouTube.

Straight Leg Pants with a Blazer

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I love a blazer all 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 in 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 belt to break up the look and add a little sophistication. Another fun way to jazz up a look is to add a pop of print like these leopard pumps. They’re a fun alternative to a neutral high heel.

Sweater Dress with a Wool Wrap Coat

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Parties don’t stop just because it’s cold outside. If you’re searching for cold weather party outfits, this is a great option to wear. This mini sweater dress is a bodycon style with beautiful, bold buttons. Don’t be afraid to wear a shorter dress in the winter. You can always wear tights and knee-high boots to add coverage to your legs.

Then, you can layer over a wool coat that’s longer in length to provide even more coverage when you’re outside. This wrap-style silhouette provides a structured look that’s flattering for all body types.

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 afterwards 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 too.

The tweed cropped 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 coral-color cardigan. I left some of the white shirt peeking out at the cuff. It elevates the look a bit more.

Jumpsuit with a Moto Jacket

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Go brunchin’ in style with this fun and flirty jump suit. I layered a moto jacket over the top. Then, I paired neutral covered-heel booties to complete this cold weather outfit.

Trench Coat with a Tunic Sweater

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If you’re headed to the beach, cute cold weather beach outfits are most likely on your packing list. This time of year, it can still be pretty chilly at many beach towns – especially in the evening. A trench coat is ideal for weather that’s prone to rain and on the chilly side. You could also wear a light puffer coat instead.

These patent boots are the perfect color for my light and airy wardrobe. They’re waterproof and will keep your feet dry.

This street style look will take you from a leisure walk on the beach to a casual dinner. Additionally, these pieces will transition well into the spring season.

Slip Skirt with a Cashmere Sweater

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This year, one of my goals is to go on a date night with Tim more often. This next round up of looks are cold weather date outfits. 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 top 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 over all look. Pair a rich espresso, knee-high boot to complete the look.

Faux Leather Pants with a Sheer Top

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Cold weather birthday outfits don’t have to be boring. I have a January birthday, and love to play with textures and feminine details to create a special night out look. These beautiful faux leather plum pants are an on-trend option to pair with boots.

Boots with a covered, skinny heel pair well with more upscale looks. They’re sleek and sophisticated and look beautiful with pants, skirts and dresses.

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 midi-length sweater dresses.

The dress on the right has a more forgiving fit. So if you want more structure, add a skinny belt to your natural waistline.

Faux Fur Jacket with Flare 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 faux fur coat is a great place to start. Then, you can build your look around that. This high-neck bodysuit layers beautifully underneath this faux fur coat, and won’t take away from it. Flare jeans are a trendy jean silhouette and are flattering on anyone. To complete the look, I paired white booties with a pointed toe.

A crossbody bag is convenient to bring to an event like a festival, so you can keep your hands free.

Chambray Top with Faux Leather Leggings

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The final two looks in this cute cold weather outfit roundup are cold weather concert looks. Depending on what type of artist you’re going to see, slightly determines what type of outfit you wear. If you’re headed to a country concert, the above outfit is a fun option to sing and dance the night away in.

The chambray shirt has a feminine vibe with puff, pleated sleeves and oversized buttons. I haven’t seen too many chambray shirts with this level of detail. To complete the look, wear Western-inspired, knee-high boots. I love these because they’re not overly “cowgirl”, but have just enough trendiness to them.

However, if you’re attending a concert with a rock or pop artist (I’m coming for you Taylor!), then you could switch the chambray shirt with a graphic tee or a bodysuit.

Maxi Dress with Booties

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If you’d rather wear a dress to a concert, this long sleeve maxi dress is perfect to pair with booties or knee-high boots. For an added layer, a faux fur vest adds texture and a little more “fun” to the look. Felt hats make great accessories to wear to events like concerts.

What’s your favorite cold weather winter outfit in this roundup? Let me know below!

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