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Thirteen Casual Chic Winter Outfits

  • December 21, 2024
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casual chic winter outfit with a beige sweater, black wool coat, black cropped pants, silver ballet flats, and a perforated cream sling bag

I’m rounding up some recent outfits I’ve worn this December. The weather is a bit up and down these days, and that is reflected in my outfit choices. These casual chic winter outfits are all simple combinations using mostly basics (with a little faux fur!) You could totally copy these looks with items from your own closet. I hope this gives you some early winter outfit inspiration!


Thirteen Casual Chic Winter Outfits

Cable Knit Sweater + Cuffed Jeans + Loafers

casual winter outfit with a cream cable knit sweater, light wash cuffed jeans, black loafers, and a black crossbody bag
Outfit details

I absolutely love a cable knit sweater. I think it’s chic and classic. This one is from Sézane so, of course, it’s beautifully made. To keep it more casual and modern, I paired it with some cuffed jeans (I went down two sizes for this fit) and some sleek loafers.


Striped Button Down + Blazer + Full Length Jeans + Heeled Boots

casual chic winter outfit with a camel and cream striped button down, camel blazer, black full length jeans, and brown heeled boots with a black leather crossbody bag
outfit details

I’m often wearing heeled boots this time of year which means I can wear my full length jeans. This combination always makes my short legs look much longer. On top, I kept it more classic with a striped button down and camel blazer. Both of these are quality staples you can wear year round.


Half-Zip Sweater + Turtleneck + Full Length Jeans + Heeled Boots

casual chic winter outfit with a black turtleneck, beige half-zip sweater, full length dark wash jeans, and black heeled boots
Outfit details

Here’s another combination with a heeled boot and full length jeans. This time with a black turtleneck and beige half-zip sweater. Adding a turtleneck (or even just a long sleeve tee) is an easy way to add warmth.


Turtleneck + Faux Fur Coat + Slim Cut Jeans + Combat Boots

casual chic winter outfit with a black turtleneck, faux fur coat, slim cut dark wash denim, black combat boots, and a black beanie
outfit details

I wore this outfit to go get our Christmas tree. I LOVED it. I have on a black turtleneck underneath this faux fur coat which is super warm and cozy. I paired it with some slim fitting jeans and combat boots for a casual yet chic outfit.


Striped Sweater + Slim Cut Jeans + Sambas

casual winter outfit with a brown and white striped sweater, slim cut jeans, tan Adidas Samba sneakers, and a cream sling bag
outfit details

I wore this easy outfit on a day I wanted to be comfy casual. This striped sweater is such good quality yet really affordable, too. I paired it with some slim cut straight leg jeans, socks, and Samba sneakers.


Plaid Shirt + Wool Coat + Sweater Over The Shoulders + Straight Jeans + Sambas

casual winter outfit with a plaid button down, straight leg jeans, tan Samba sneakers, black wool coat, beige sweater worn over the shoulders, and a black leather crossbody bag
outfit details

I love how this look came together. I paired a plaid oversized button down with some straight leg jeans and Samba sneakers. I also added a wool coat and a sweater over the shoulders for dimension and interest. Plus, it acts as a scarf keeping you just a bit warmer.


Lady Jacket + Straight Jeans + Heeled Boots

casual chic winter outfit with a black lady jacket, dark wash straight leg jeans, black heeled boots, and a black crossbody bag
outfit details

This look felt very Parisian chic, and I was into it! This is the Betty Cardigan from Sézane (see more ways to style it here!) I own it in this black crochet version and also in the ecru. I kept it simple with a pair of dark wash straight leg jeans and heeled black boots. I also added a wool coat.


Tee + Cardigan + Raincoat + Slim Cut Jeans + Sneakers

casual winter outfit with a gray tee, brown wool cardigan, beige rubber raincoat, straight leg jeans, tan Samba sneakers, and a cream sling bag
outfit details

I wore this look to do a little vintage shopping on a Saturday afternoon. It was rainy and cool so my rubber raincoat was necessary. The rest of the outfit is a gray tee under a Sézane cardigan with some slim cut jeans, and Samba sneakers. I added this cool sling bag as well which you’ll see in several of my outfits here.


Button Down + Sweater Over The Shoulders + Straight Jeans + Loafers

casual chic winter outfit with a white button down, gray sweater worn over the shoulders, dark wash straight leg jeans, black loafers with gray socks, and a black leather crossbody bag
outfit details

This here is an outfit combination I wear often in the cooler months – an oversized button down with a sweater over the shoulders, straight leg jeans, and loafers. I actually matched my sweater to my socks which felt like a nice touch.


Turtleneck + Button Down + Sweater Over The Shoulders + Straight Jeans + Heeled Boots

casual chic outfit idea with an oversized blue denim button down, a brown turtleneck, straight leg jeans, brown heeled boots, a cable knit sweater worn over the shoulders, and a brown sling bag
outfit details

This outfit is very similar to the one above except I added a turtleneck underneath my button down and swapped the loafers for ankle boots. I wore this on a casual weekday working from home and hanging out with my kids after school.


Lady Jacket + Barrel Jeans + Chelsea Boots

casual chic outfit idea with an ecru lady jacket, black barrel jeans, brown chunky chelsea boots, and a brown suede sling bag
outfit details

It was another rainy day so I pulled out my go-to water-resistant Chelsea boots from Frēda Salvador. These are pretty pricey, but they are so well made and also super lightweight. I paired them with a lady jacket, barrel jeans, and suede sling bag for a casual yet elevated look.


Beige Sweater + Cropped Black Pants + Silver Ballet Flats + Wool Coat

casual chic winter outfit with a beige sweater, black wool coat, black cropped pants, silver ballet flats, and a perforated cream sling bag
outfit details

I had just gotten my hair done so, of course, some nice outfit photos had to happen. This look includes a beige sweater from Quince, cropped black pants from Anthropologie, silver ballet flats from Dolce Vita, and a wool coat from Mango.


Black Sweater + Black Jeans + Black Boots + Faux Fur Coat

casual chic winter outfit with a black sweater, black straight leg jeans, black heeled boots, a faux fur coat, and a black crossbody bag
outfit details

I wore this outfit to do a little last minute Christmas shopping. It felt chic and put together. I’m wearing a simple black cashmere sweater, black straight leg jeans, black heeled boots, and my faux fur jacket.


Read More:
Eleven Everyday Casual Chic Fall Outfits
Classic Winter Workwear Capsule Wardrobe

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