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February 4, 2021

20 Casual & Dressy Winter Outfit Ideas

 

The winter season is in full swing!  Today, we are celebrating the cooler months by sharing 20 of our favorite winter outfit ideas to help you survive the next few months. 

 

WINTER OUTFIT IDEAS WITH JEANS

With cold weather officially here, we wanted to share a few of our favorite cute winter outfits – both dressy and casual. 

Whether you’ve been getting dressed up these last few months, or have been staying at home and dressing more casually, the winter outfit ideas below will hopefully help you ring in the winter months and holiday in style (and comfort).  

What I love about these outfits for winter is they are not just appropriate for the holiday season, but all Fall and Winter long.  The majoirty of the looks are geared towards a more casual setting, but at the bottom of the post, I also wanted to include a few outfit ideas for those dressing up more frequently.  

Also, we wanted to make sure these looks were easy to recreate from things you already own in your closet. 

Many, if not most, of these winter outfit ideas are easy to swap out for even more comfort.  For example, for outfits including faux leather pants, or straight jeans, feel free to swap those out for comfortable leggings or even joggers.  

If you are looking for even more ways to look stylish this Fall & Winter, be sure to see the post 25 Cute & Casual Thanksgiving Outfit Ideas

 

OUTFIT DETAILS:  FLARED JEANS || ANKLE BOOTS || LONG BLACK COAT (similar affordable wool coat. I also love this belted wool coat) || SWEATER (similar leopard sweater) || STAUD BUCKET BAG

 

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If you’re looking for a pair of jeans you can also dress up this Fall & Winter, these wax jeans from Abercrombie are an awesome option.  They fit really well and the wax like design gives them a similar look to leather pants, but are so soft and comfortable.  

They pair so well with a beautiful sweater or blazer for a pulled together Christmas or Thanksgiving outfit.  Or, pair this jeans outfit with a more formal top for a casual New Years Eve outfit.  

As for the fit of these jeans, they are available in short, regular and tall.  I ordered in a 27 short for reference.  

 

OUTFIT DETAILS:  SIMILAR OVERSIZED BLAZER || JEANS || BLACK SUEDE BOOTS ||  STAUD BUCKET BAG|| SILK CAMI

 

SHOP THE LOOK

 

 

 

If you’re in an area where the temperatures are just a bit warmer in the winter months, try layering your classic utility jacket with jeans, a button down top and a black belt bag.  It’s the perfect casual winter outfit idea you can easily carry into Spring, as well. 

 

OUTFIT DETAILS:  FLARED JEANS || ANKLE BOOTS || WHITE BUTTON DOWN || SIMILAR UTILITY JACKET || SIMILAR BELT BAG

 

SHOP THE LOOK

 

 

 

Want a cute winter outfit with a little more edge?  Choose a graphic tee and blazer.  If you want to add even more detail, you can also wear the same look faux leather pants with statement heels.  

 

OUTFIT DETAILS:  SIMILAR LONG GREY CARDIGAN || JEANS || BLACK SUEDE BOOTS || SIMILAR GRAPHIC TEE 

 

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I was initialy uncertain about these high waisted flare jeans until they arrived in the mail.  If you’re looking for a way to add a little extra touch to your winter outfits this season, I recommend a pair of wide leg jeans or flare jeans.  You can often find a great variety at Mango.  

I really love how these jeans pair perfectly with a crisp white button down and black leather jacket.  If you need some winter outfit inspiration, give this cute outfit a go.  

 

OUTFIT DETAILS:  SIMILAR FLARED JEANS || ANKLE BOOTS || WHITE BUTTON DOWN || LEATHER JACKET || EARRINGS || STAUD BUCKET BAG

 

SHOP THE POST

 

 

 

Can you tell we love these black jeans?  They are so versatile and comfy.  Need another way to style them?  Choose a simple tank and an open cardigan and you’re good to go!  This look makes for a simple, but chic look for date night, coffee with the girls and more.  

 

OUTFIT DETAILS:  SIMILAR LONG GREY CARDIGAN || JEANS || BLACK SUEDE BOOTS || TANK || STAUD BUCKET BAG

 

 

This winter outfit idesas post would not be complete without a casual outfit paired with a camel winter coat.

I normally gravitate towards my skinny jeans, but these flared jeans have quickly become one of my favorite pair.  The high waist and button front are so flattering and lengthening – not to mention comfortable and cute.  

For this stylish winter outfit, we chose a blouse we’ve had in our closet for the last few years along with ankle boots and a long tan coat.  Again, these looks are meant to inspire you to choose pieces from your closet as opposed to buying someting new, when possible.  We have included a few of our favorite top options below.  

 

OUTFIT DETAILS:  LONG TAN COAT (SIMILAR STYLES HERE, HERE & HERE) || FLARED JEANS || ANKLE BOOTS || BLOUSE (SOLD OUT) || HANDBAG

 

SHOP THE LOOK

 

 

 

Looking for a way to wear your favorite sweatshirt outside of the house this season?  Recreate this winter outfit idea with ankle booties and your favorite black jeans!

 

OUTFIT DETAILS:  SWEATSHIRT || JEANS || BLACK SUEDE BOOTS ||  STAUD BUCKET BAG

 

SHOP THE LOOK

 

 

 

If you’re looking for a casual winter outfit idea that still feels pulled together, I love skinny jeans paired with a striped sweater and classic winter coat.  What I love most about this look is the multiple ways it can be styled.  Dress it down with sneakers or dress up with faux suede pants.

 

OUTFIT DETAILS:  LONG TAN COAT (SIMILAR STYLES HERE, HERE & HERE) || JEANS || HEELS || STRIPE SWEATER (SIMILAR STYLE) || BAG

 

 

 

If you have been following the blog for any time now, you know we are a big fan this J.Crew wool coat.  The vibrant color options help elevate just about any Fall or Winter look.  

Keeping with the skinny jean trend, we have fallen in love with this plaid top and heels.  It’s a cute Thanksgiving outfit for a small, intimate dinner or look for home.  

Bonus, both the winter coat and plaid top are now on sale.  As for sizing, I definitely recommend sizing down in the coat (I bought an XXSmall) and up slightly in the top (size 4). 

I love this wool jacket so much I have purcahsed it in several colors.  I can almost guarantee you’ll love it as much as I do.  It’s a great coat for anyone currently living with more mild winter temperatures.  

 

OUTFIT DETAILS:  LONG RED COAT (SIMILAR STYLES HERE, HERE & HERE) || SKINNY JEANS || BLACK SUEDE HEELS || PLAID BUTTON DOWN || HANDBAG

 

SHOP THE LOOK

 

 

 

OUTFIT DETAILS:  FLARED JEANS || ANKLE BOOTS || LONG WOOL COAT || WHITE BUTTON DOWN || STAUD BUCKET BAG

 

 

WINTER OUTFITS WITH LEGGINGS

If you love your faux leather leggings as much as we do, we have a few cute winter outfit ideas with leggings for you below.  

First, you’ll see me pair my faux leather leggings most with my knee high boots or sneakers.  I love how the winter outfit above came together paired with my favorite utility jacket and boots.  Want to give this winter outfit a little more ‘umph’.  Add a belt.  This is definitely an outfit to copy all season long.  

 

OUTFIT DETAILS:  FAUX LEATHER LEGGINGS || BLACK OVER THE KNEE BOOTS || WHITE BUTTON DOWN || TORY BURCH REVERSABLE BELT || SIMILAR UTILITY JACKET || STAUD BUCKET BAG

 

 

 

Want a winter outfit idea with a pop of color?  Winter dressing is made easy with faux leather leggings paired with a long, cozy knit in a vibrant color.  They pair perfectly with a black and white coat and knee high boots.

 

OUTFIT DETAILS:  FAUX LEATHER LEGGINGS || BLACK OVER THE KNEE BOOTS || SWEATER || SIMILAR BLACK & WHITE COAT || STAUD BUCKET BAG

 

 

If you want a cute winter outfit idea that’s more on the causal side, take your favorite utility jacket and pair it with your favorite white sneakers, a crsip white or grey tee and you’re ready for weekend of errands.  Don’t forget a cute crossbody bag, too. 

 

OUTFIT DETAILS:  FAUX LEATHER LEGGINGS || SNEAKERS || WHITE BUTTON DOWN || SIMILAR UTILITY JACKET || BLACK CROSSBODY BAG

 

 

OUTFIT DETAILS:  FAUX LEATHER LEGGINGS || BLACK OVER THE KNEE BOOTS || SIMILAR OVERSIZED SWEATER || STAUD BUCKET BAG

 

 

OUTFIT DETAILS:  FAUX LEATHER LEGGINGS || SNEAKERS || WHITE BUTTON DOWN || OVERSIZED DENIM JACKET || BLACK CROSSBODY BAG

 

DRESSY WINTER OUTFIT IDEAS 

 

Winter style doesn’t have to be boring.  The next few photos are cute winter outfit ideas paired with a classic little black dress.  If you haven’t already invested in a classic LBD, get your hands on one stats.  What I love most about a LBD are the countless ways you can style them for every season.  

For the look above, we wanted to contrast the dress outfit with brown tones.  Pair with any brown over the knee boots and a plaid coat for a classy outfit perfect for date night, the office any beyond. 

 

OUTFIT DETAILS:  LITTLE BLACK DRESS || SIMILAR OVER THE KNEE BOOTS || SIMILAR PLAID COAT || REVERSABLE BELT || BLACK CROSSBODY BAG

 

 

This plaid coat is by far one of my closet favorites.  If you’re looking for a more dressy winter outfit idea you can never go wrong with an all black look.  We added the plaid coat to add a bit of flavor to the look, but as you can see in the look below, we also love it with a classic black or tan coat, too.  

 

OUTFIT DETAILS:  LONG PLAID COAT (SIMILAR STYLES HERE, HERE & HERE) |OVER THE KNEE BOOTS ||

 

 

OUTFIT DETAILS:  LITTLE BLACK DRESS || SIMILAR OVER THE KNEE BOOTS || SIMILAR PLAID COAT || REVERSABLE BELT || BLACK CROSSBODY BAG

 

 

OUTFIT DETAILS:  LITTLE BLACK DRESS || SIMILAR OVER THE KNEE BOOTS || SIMILAR PLAID COAT || REVERSABLE BELT || BLACK CROSSBODY BAG

 

 

LOOKING FOR OTHER GREAT OUTFIT IDEA POSTS?  HERE ARE JUST A FEW OF OUR FAVORITES: 

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