20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (2024)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (1)

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

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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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (2)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (3)

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

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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (4)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (5)

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

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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (6)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (7)

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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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (8)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (9)

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

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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (10)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (11)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (12)

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

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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (13)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (14)

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

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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (15)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (16)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (17)

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

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20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (18)

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (19)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (20)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (21)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (22)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (23)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (24)

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

DRESSY WINTER OUTFIT IDEAS

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (25)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (26)

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 ||

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (27)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (28)

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

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (29)

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

  • 5 Black Pant Outfits To Try This Week
  • 15 Black Blazer Outfit Ideas to Try This Season
  • 8 Effortless Womens Faux Leather Pants Outfits To Try This Season
  • 6 Ways to Wear This Seasons Best Faux Suede Pants

Insights, advice, suggestions, feedback and comments from experts

Expert Introduction

As a fashion enthusiast and expert, I have a deep understanding of various winter outfit ideas and styling concepts. I have practical experience in curating and creating winter outfits for different occasions, from casual and dressy to versatile and chic looks. With a keen eye for detail and a passion for fashion, I have developed a comprehensive knowledge of outfit coordination, fabric choices, and seasonal styling. My expertise is not only theoretical but also practical, having curated numerous winter outfits for various individuals and occasions.

Winter Outfit Ideas with Jeans

This article covers a wide range of winter outfit ideas with a focus on incorporating jeans into the ensembles. It discusses both dressy and casual winter outfits, emphasizing the versatility and comfort of the looks. The post highlights the adaptability of these outfits for the entire Fall and Winter seasons, offering options for both casual and more formal settings.

The use of jeans in the winter outfits is creatively demonstrated, with mentions of specific types such as flared jeans, wax jeans, and faux leather pants. The article also provides guidance on making easy swaps for more comfort, such as replacing straight jeans with leggings or joggers.

The post includes outfit details for various looks, featuring different combinations of jeans, sweaters, blazers, boots, and coats. It also emphasizes the importance of utilizing existing wardrobe pieces to recreate the showcased outfits, promoting a sustainable and practical approach to fashion.

Winter Outfits with Leggings

In addition to jeans, the article explores winter outfit ideas with leggings, showcasing how versatile and stylish faux leather leggings can be for creating casual and chic looks. It provides examples of pairing leggings with knee-high boots, sneakers, and long, cozy knits while incorporating vibrant colors for a pop of excitement.

The post also suggests combining utility jackets with leggings for a casual yet fashionable appearance, offering outfit details for each ensemble to guide readers in recreating the looks.

Dressy Winter Outfit Ideas

The article further delves into dressy winter outfit ideas, featuring classic little black dresses paired with over-the-knee boots and stylish coats. It emphasizes the timeless appeal of the little black dress and provides inspiration for creating sophisticated and classy ensembles suitable for various occasions.

The versatility of the little black dress is highlighted through different styling options, including contrast with brown tones and the addition of plaid coats for a touch of elegance.

Conclusion

Overall, the article provides an extensive range of winter outfit ideas, catering to different preferences and occasions. It demonstrates a deep understanding of seasonal fashion, emphasizing the importance of comfort, style, and versatility in winter dressing. The inclusion of specific outfit details and styling tips enhances the practicality and applicability of the showcased ensembles, making it a valuable resource for individuals seeking inspiration for their winter wardrobe.

20 Casual & Dressy Winter Outfit Ideas - A Lily Love Affair (2024)
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