9 Cute Winter Outfits for 2020

Looking for cute winter outfits for 2020? Here are nine of my favorites to copy:

9 Cute Outfits for Winter

1. Winter Vest

Shirt: Express | Vest: Cupcakes and Cashmere | Jeans: BLANKNYC | Bag: Rebecca Minkoff | Boots: sold out, similar here and here | Bracelets: David Yurman, Kate Spade

Since winter is almost here and the temperatures have started to drop, I wanted to share my favorite ways to wear a winter vest this season. In the photos above, I paired my vest with a plaid shirt, jeans, and OTK boots, but there are several other ways to wear vests this winter! Shop my favorite outfits with this winter vest below.

There are countless ways to style vests in the winter, but those are my top favorite outfits to wear with a vest.

2. Favorite Cozy Knitted Sweater

There’s seriously nothing better than finding the perfect sweater for wintertime that is so comfy and cozy and can be paired with literally anything. This cozy knit sweater is my favorite sweater find this season! I love long sweaters because they keep you warmer and I think they are super flattering on any body type. Express has been my one stop shop for sweaters this year. I bought this pale lavender sweater at the same time I got this one, and I just saw this chenille sweater today that I love (and it’s on sale!) Express always seems to have some sort of sale going on which is super nice when you are wanting to stock up on some basics.

If you are in need of some new cozy and stylish sweaters this season, I’ve got you covered! I have rounded up some of the cutest and most affordable sweaters that would be a perfect addition to your closet, and they would also make great gifts! Just an FYI, I normally order down a size when I buy from Express. Almost every sweater I have from them is a size small. Let me know if you have any questions about the sweaters, sizing, etc!

My Outfit Details:

Sweater: Express, other colors here | Tank: BP (old), similar here | Jeans: AG Jeans | Belt: Free People | OTK Boots: Steve Madden (old), similar here | Crossbody Bag: Rebecca Minkoff | Necklace: BP (sold out), similar here

Photo Credit: Joan Fisher

3. My Favorite Holiday Party Dress

When I think of the perfect holiday dress, a few things come to mind: the color, the fit, and the material are very important details! This burgundy dress checks all the boxes for me when it comes to the perfect dress! I love the color, the silky material (which makes it look and feel more holiday-like), and I love that the dress is cinched at the waist for a more flattering style! The best part about this dress is that it is currently marked 40% off and it is less than $30!!! It comes in 6 colors which are all beautiful options!

I love that you can easily dress this outfit up or down depending on how casual/fancy the party is that you are attending. I styled it with a wool hat and OTK boots, but to dress it up even more you could add a leather jacket, fur stole, and heels! To dress it down, you could wear ankle booties and a jean jacket. The versatility of this dress is what makes it so amazing!

What holiday parties do you have coming up?? Make sure to check out this dress if you haven’t found the perfect thing to wear yet!

POST DETAILS:

Dress: Lush (40% off!) | Hat: Rag & Bone | OTK Boots: Steve Madden | Bag: Rebecca Minkoff | Watch: Michele | Bracelet: Kate Spade | Earrings: Halogen

Photo Credit: Joan Fisher

4. Mad for Plaid and Leather

I want to share a combo that I’ve been loving lately which is plaid and leather. I think plaid is generally thought of as a print that is casual and that’s normally dressed down, but I am obsessed with pairing it with leather and dressing it up. This could be a perfect outfit for a holiday party or even for a NYE party! I mentioned in this post how obsessed I am with these faux leather leggings– I just can’t stop wearing them! They seriously go with any outfit and they dress everything up 100x more than regular leggings would.

Not only do I wear those leggings non-stop, but I also can’t stop wearing this jacket. I included this leather jacket in my women’s gift guide video because EVERY woman needs it and it’s under $100. I talk about this in my video, but one of the main reasons I love the leather jacket so much is because it has gold hardware on it. Most leather jackets have silver zippers and buttons and this jacket has gold, which is perfect for people like me who mostly wear gold earrings and necklaces. If you know someone who loves wearing gold jewelry then you must get them this leather jacket for Christmas…they will greatly appreciate it!

Outfit Details:

Plaid Shirt: Loft (old), similar here | Leather Jacket: BLANKNYC | Faux Leather Leggings: ASSETS by Spanx | OTK Boots: Nordstrom | Bag: Rebecca Minkoff | Necklace: Urban Outfitters | Sunglasses: DIFF Eyewear (Use code JOYFULLY25 for 25% off any pair!)

Photo Credit: Joan Fisher

5. How to Stay Warm and Look Cute

JACKET: Michael Kors, similar here | JEANS: Articles of Society (only $59!) | OTK BOOTS: Steve Madden (sold out), similar here and here | BAG: Rebecca MinkoffSCARF: Nordstrom, similar here and here | MITTENS: North Face | HAT: Nordstrom (sold out), similar here

I want to share my tips on how to look cute in the cold weather while still staying warm!

This past weekend I was in Chicago where it was FREEZING cold, but luckily I was prepared with a warm coat and accessories. When you live in a cold climate, I think it’s important to know how to stay warm while still looking cute. When I am going on a date with my husband or out with my friends, I don’t want to look frumpy in a big puffy coat. I want to look fashionable but I don’t want to freeze. I have come up with several tips on how to stay warm and look cute!

  1. Find a warm and flattering coat

This first tip is very important! When you are dressing for cold weather but still wanting to look cute, find a coat that somewhat shows off your silhouette. There are many coats with waistbands and/or ties around the waist that show off your figure but still keep you nice and warm.

2. Wear a statement scarf

When you are trying to dress to impress in the cold, a statement scarf is just the thing you need! There are so many options of statement scarves but some of my favorites are plaid blanket scarves and fur stoles. Whatever you decide to wear, make sure it stands out.

3. Find Cohesive Accessories

One of the most important accessories to wear in cold weather is a hat. I am a huge fan of beanies, especially cute, feminine ones with a little pom pom at the top. Whatever hat you decide to wear, make sure it goes with the other accessories you pair it with- gloves, scarf, etc. You want there to be a theme with your accessories, but they don’t have to be completely matchy matchy. In my outfit pictured above, all of my accessories are in the blush pink, purple, and gray family. You want your whole look to be cohesive, but not identical.

4. Layer up

Underneath your jacket, make sure you are wearing a few layers. You can wear a long-sleeved shirt, turtleneck, sweater or vest under your coat. The more layers you wear, the warmer you will be.

5. Wear multifunctional boots

Not only are over the knee boots super on trend and fashionable, but they actually serve another purpose in the colder months! OTK boots add an extra layer to your legs and keep you super warm! While they won’t keep your feet as warm as snow boots would, they will provide an extra layer of warmth to your legs. If you are going out on the town, ditch the snow boots for one night and throw on some OTK boots! Just make sure to wear a thick pair of socks to keep your feet warm.

6. How to Wear a Sweater Dress With Boots

Sweater Dress: Madewell (Sold out), Similar | Boots: Steve Madden | Scarf: Nordstrom (Sold out), Similar | Bracelets: Hermes, David Yurman | Watch: Michele

Sweater weather is my favorite weather, and I especially love wearing sweater dresses! When it’s really cold outside but I still want to be dressed up, I will wear a sweater dress with over the knee boots. Not only does this outfit keep me warm in chilly temperatures, but it also looks polished and fashionable.

You can also wear sweater dresses with tights and booties or riding boots. If you are going to wear shorter boots that will expose more of your legs, I highly suggest wearing black tights with your sweater dress in the fall and winter.

Sweater dresses are easy to wear and you can style them many different ways. I added a scarf to my outfit, but you could also add a jacket, a beanie, a wool hat or a vest…the list goes on and on!

I love stocking up on my sweater dresses before wintertime so I can be assured my favorite ones don’t sell out.

7. Cozy + Cute Winter Outfit

If you can’t tell by now, I loooove sweaters, especially ones that are soft and warm. This sweater is made of the softest material and it keeps me really warm, so it definitely passes my sweater test with flying colors. I love adding fun and wintery accessories to my winter outfits like this beanie and scarf. These accessories would both make great Christmas gifts! I included this pom pom beanie in my women’s gift guide video– have you seen it yet?! If not, you should check it out here. I rounded up the best gifts for all of the women in your life! If you are still needing gift suggestions for your mom, sister, BFF, etc., make sure you watch this video to get some great gift ideas. PS- I’m wearing the same gray sweater that’s pictured above in my women’s gift guide video, so you can see another way I style it!

POST DETAILS:

Sweater: BP (Love this sweater! Comes in 4 other colors) | Jeans: AG Jeans | Hat: Treasure & Bond | Scarf: Nordstrom (old), similar here | Bag: Rebecca Minkoff | Booties: Sam Edelman

Photo Credit: Joan Fisher

8. 5 Winter Wardrobe Essentials You Need

Dressing for winter weather can sometimes be tricky, especially if you have somewhere nice to go and you want to wear a cute outfit! The key to dressing well in the wintertime is making sure you own a few key items in your winter wardrobe that will elevate any outfit. I am sharing the 5 items that every woman needs in her winter wardrobe below.

[ONE] Skinny Jeans

Skinny jeans are a year round wardrobe must have in my opinion, but you really need a good pair in the winter! Skinny jeans are a necessity because they are tailored which makes them very flattering on any figure, and they are thin enough and skinny enough at the bottom to be paired with any type of boot.

[TWO] Warm Sweater

Sweaters are an absolute staple in any winter wardrobe! It’s important to find some sweaters that are warm but are still thin enough to comfortably fit under a jacket or a sweater.

[THREE] Classic Wool Coat

A wool coat is a timeless piece that you can wear for many winters to come. Wool coats are the perfect addition to any outfit to dress it up! This is my absolute favorite wool coat- I removed the fur collar and added a fur scarf to mine instead! You can wear this coat over ANY outfit this winter and it will pull the look together perfectly.

[FOUR] Faux Fur Scarf

Faux fur is a trend we are seeing like crazy this winter, and it’s also a total winter wardrobe must have! If you aren’t yet ready for the full on faux fur coat trend, try out the faux fur scarf to add a little fur to your look. Not only are faux fur scarves beautiful and trendy, but they also keep you really warm. Throw on the scarf over a wool coat, leather jacket, suede jacket or even pair it with a sweater.

[FIVE] Over the Knee Boots

I sound like a broken record when talking about over the knee boots because I think EVERY woman needs to own a pair! They dress up any outfit and the best part is they keep your legs extra warm in the cold winter months.

Do you own all 5 of these items in your winter wardrobe?? Leave me a comment down below and let me know!

POST DETAILS:

Sweater: BP | Wool Coat: Topshop | Faux Fur Scarf: Topshop | Jeans: AG Jeans | OTK Boots: Steve Madden (old), similar here | Crossbody Bag: Rebecca Minkoff

 

9. NYE Must Have Accessories

Tank: old, similar here | Jeans: BLANKNYC | Leather Jacket: BLANKNYC | Heels: Express (so comfy for heels!)| Necklaces: BaubleBar, Urban Outfitters | Fur Stole: Sole Society (sold out), similar here | Bag: Rebecca Minkoff

There is always a huge build up for NYE outfits and it makes dressing for the holiday way more stressful than fun. Don’t get me wrong, finding the perfect sequin dress to wear would be amazing, but not everyone has a formal event to attend on New Year’s Eve. This year, I wanted to share accessories that are perfect for NYE. I always ring in the new year with my family at a casual get together. I still want to look festive without going overboard, so adding a few fun accessories to my outfit will do the trick.

NYE Must Have Accessories

Necklaces: I love layering necklaces, especially when a choker is involved. I actually bought this BaubleBar choker for an upcoming trip to Vegas, but I thought it would be perfect for NYE. Anything that sparkles will work just fine for New Years 🙂 I also had this other layered necklace from Urban Outfitters that paired very nicely with the choker. Jewelry is supposed to make a statement, so don’t be afraid to let it speak for your outfit on NYE.

Fur: This black fur stole was one of my favorite Christmas presents this year. Adding a fur stole or scarf to a regular old leather jacket adds a glam factor that works perfectly for NYE.

Handbag: I ordered this velvet Rebecca Minkoff bag on Cyber Monday, and I knew I had to wear it on NYE. Anything velvet=holiday, so don’t shy away from it this weekend.

Shoes: Like jewelry, shoes also make a big statement. If you are going to a casual get together on NYE, you can wear jeans and add some heels to dress the outfit up a bit. These caged heels from Express are surprisingly comfortable and easy to walk in. That’s a huge plus if you are going to be on your feet all night!

More Winter Outfits Coming Soon!

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67 thoughts on “9 Cute Winter Outfits for 2020”

    • Thank you Mary!! OTK boots are seriously my favorite fall and winter shoe to wear!! You should definitely get a pair 🙂 Thanks so much for reading my blog! xo, Kimmie

      Reply
  1. I am in LOVE with this look. First off, YOUR. HAIR. Love it.
    Also I love how you paired this cozy sweater dress and scarf. Your jewelry has to be my favorite part though. I own that white Hermes bracelet and wear almost every day but the Michelle watch is most definitely at the top of my wanted list.

    Reply
    • Thank you so much Macey, I’m so glad you like it! The Hermes bracelet was a wedding gift from my husband and I seriously wear it everyday…I’m obsessed! You have to get the Michele watch- put it on your bday or Christmas list 🙂 It goes with everything and is the perfect everyday watch! Thanks for stopping by! xo, Kimmie

      Reply
  2. Ummmm first of all: the new site layout is GORGEOUS! Secondly, I’m loving your outfit here and the suggestions for winter weather! So many great things happening right now!

    Reply
    • Aww thank you so much, Mary! Fur scarves are the best winter accessory! I’m so happy you like my new site- thanks for letting me know 🙂 xo Kimmie

      Reply
  3. I’m not sure I can pick one piece I love more than the others because everything you’re wearing is beyond cute! You sure look cozy in that hat and scarf combo!

    Reply
  4. Accessories can make or break and outfit, and girl you killed it! Love the pops of red, and that scarf is beautiful! Goes so well with your hat and sweater. Really a well styled look, and so perfect for a casual winter day!

    xoxo Bryanna | Coming in Clutch

    Reply

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