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How To Wear Dresses in the Winter and Stay Warm

As a petite woman, dresses are my favorite thing to wear. Dresses are so flattering on a petite frame, as they serve to lengthen the appearance by creating a vertical line. A dress naturally accents the curves on any woman, and this is especially true for petite women. If I could wear a dress every day I would, as I just love the way I look in them! In the winter however, this isn’t always practical. Today I am sharing eight inspiring ways to wear dresses in the winter, and at the same time stay warm!

Petite Fashion and Style Blog | Dr. Scholls Custom Fit Orthotics | Wayf Maddi Wrap Mini Dress | Stuart Weitzman Highland Boots | Click to Read More...

Pair a Long Sleeve Dress with Over The Knee Boots

Over the knee boots are a winter wardrobe staple for me! I love them for multiple reasons. They are actually warmer than pants as they are obviously thicker and more durable. When paired with an above the knee dress, OTK boots with a heel serve to lengthen my legs and make me look taller than I really am. Finally, most OTK heeled boots I own are very comfortable, and I can wear them all day without significant pain. My all time favorite are Stuart Weitzman but I also have found this season’s Tory Burch OTK boots to be equally as nice and more affordable. 

Petite Fashion and Style Blog | Dr. Scholls Custom Fit Orthotics | Wayf Maddi Wrap Mini Dress | Stuart Weitzman Highland Boots | Click to Read More...Petite Fashion and Style Blog | Dr. Scholls Custom Fit Orthotics | Wayf Maddi Wrap Mini Dress | Stuart Weitzman Highland Boots | Click to Read More...

The dress I am wearing is by one of my favorite new brands, Wayf. This adorable Maddie Wrap Mini Dress looks great styled with OTK boots. Even better this dress is on sale for under $40! Make sure to size up one size only because it is somewhat tight in the sleeves. 

Pair a Short Sleeve Dress with a Leather Moto Jacket

Petite Fashion and Style Blog | Fashion for Petite Women | Blank NYC Faux Leather Moto Jacket Original Post

Pairing a leather moto jacket with a dress is a great way to wear dresses in the winter. This Blank NYC faux leather moto jacket is nice as it looks realistic and is so stylish! This is one of my favorite professional looks from last year. I love the color combination of olive and black. The leather jacket complements the olive leopard print and it adds a sophisticated flair to this look.

Petite Fashion and Style Blog | Fashion for Petite Women | Burberry Daylesmore Coat | Fur Vest | Vince Camuto OTK Suede Boots

Layer a Fur Vest Over a Dress

As I mentioned in this post, a faux fur coat has the added benefit of warmth. A fur vest is fun to layer over dresses in the winter and it is also warm and stylish! I like pairing fur with stripes as the mix of patterns and textures goes well together. I love this fur vest from Old Navy. It is from the kids section, however the XXL size fits well on me as a petite woman. 

Petite Fashion and Style Blog | Fashion for Petite Women | Burberry Daylesmore Coat | Fur Vest | Vince Camuto OTK Suede BootsPetite Fashion and Style Blog | Fashion for Petite Women | Burberry Daylesmore Coat | Fur Vest | Vince Camuto OTK Suede Boots

Wear a Cardigan over a Dress

Petite Fashion and Style Blog | Fashion for Petite Women | Cascade Cardigan Original Post

It almost goes without saying that a cardigan over a dress is a great way to style it in the winter. I love the feminine styling of a cascade cardigan and it can be worn with so many things! Here I am wearing it with a skirt, but it could easily be styled with a dress. The one I am wearing is sold out, but this cardigan from Loft is very similar (and it is 50% off!). Recreate this entire look with this sweater and this skirt.

Wear a Turtleneck over A Dress

Petite Fashion and Style Blog | Fashion for Petite Women | J. Crew Cambridge Cable Crewneck Sweater Original Post

Again here I am wearing this sweater with a pleated skirt. You could also easily wear a plaid sheath dress with a turtleneck sweater and OTK boots for an instantly warm and chic look! 

Wear Leggings under the Dress

Petite Fashion and Style Blog | Fashion for Petite Women | Bloomingdale's Aqua Cashmere Turtleneck | Asos Petite Mini Flippy Skirt in Check | How To Wear Dresses in the Winter and Stay Warm

The key to wearing dresses in the winter is to keep as much of your bare skin covered as possible. While the example here is a skirt, tights can be worn with just about any winter dress, particularly if it is made of a thicker material such as wool. Cashmere is especially warm and made for the colder winter months. I love this Bloomingdale’s Aqua turtleneck sweater, and it comes in 11 colors! Take it a step further and wear this cashmere dress with tights and boots, and you will be warm and toasty all day long!

Petite Fashion and Style Blog | Fashion for Petite Women | Bloomingdale's Aqua Cashmere Turtleneck | Asos Petite Mini Flippy Skirt in Check | How To Wear Dresses in the Winter and Stay Warm

Petite Fashion and Style Blog | Fashion for Petite Women | Bloomingdale's Aqua Cashmere Turtleneck | Asos Petite Mini Flippy Skirt in Check | How To Wear Dresses in the Winter and Stay WarmPetite Fashion and Style Blog | Fashion for Petite Women | Bloomingdale's Aqua Cashmere Turtleneck | Asos Petite Mini Flippy Skirt in Check | How To Wear Dresses in the Winter and Stay Warm

Petite Fashion and Style Blog | Fashion for Petite Women | Bloomingdale's Aqua Cashmere Turtleneck | Asos Petite Mini Flippy Skirt in Check | How To Wear Dresses in the Winter and Stay Warm

Wear a Vest and Scarf Over a Dress

Petite Fashion and Style Blog | Fashion for Petite Women | J. crew Factory Printed quilted puffer vest Original Post

For a fun and casual look, wear a vest over a simple jersey dress. This plaid vest has been popular for years, and I can see why! Add a plaid scarf to mix patterns and colors, and this layered outfit is sure to keep you warm in the winter. 

 

 

Wear a Blouse Under a Sleeveless Sheath Dress

One of my favorite ways to style a dress in the winter is to wear a blouse underneath it. A sheath dress is traditionally worn alone or with a sweater, but a blouse underneath it is just as stylish. If you are wearing a solid colored dress, wear a patterned top, but if you dress is patterned wear a solid color top. 

Petite Fashion and Style Blog | Fashion for Petite Women | Pink Sheath Dress | Polka Dot Blouse | YSL Wallet on Chain | How to Wear a Dress in the Winter |

Petite Fashion and Style Blog | Fashion for Petite Women | Pink Sheath Dress | Polka Dot Blouse | YSL Wallet on Chain | How to Wear a dress in the Winter Petite Fashion and Style Blog | Fashion for Petite Women | Pink Sheath Dress | Polka Dot Blouse | YSL Wallet on Chain | How to Wear a Dress in the Winter |
Petite Fashion and Style Blog | Fashion for Petite Women | Pink Sheath Dress | Polka Dot Blouse | YSL Wallet on Chain | How to Wear a Dress in the Winter |

I hope you have found lots of inspiration in this post for wearing dresses in the winter! As Diane von Furstenburg once said, “feel like a woman, wear a dress!”. Just because the cold and wintery weather is here for now, doesn’t mean you have to compromise on style.

So how would you style dresses in the winter? Leave a comment below.

As always, thanks for looking!

xo | April

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22 thoughts on “8 Inspiring Ways to Wear Dresses in the Winter and Stay Warm…

  1. I love to wear dresses too, but I’m not in the mood for them every day. You have lovely combinations and all the boots are so pretty. I like to pair long sweaters to with a skirt or high wist skirts too 🙂

  2. I love these looks! I don’t own over-the-knee boots, but I may need to invest in a pair. I am going to a wedding next weekend, so this is great for inspiration on what to wear.

  3. You have come up with some really great looks! I am a huge boot lover, so all of those boots make me want to buy another pair!

  4. Oh my goodness I totally love all of these super cute outfits!!! I absolutely love your taste in clothes and they all look fabulous on you!

  5. Oh Thanks for this. For past so many years I pack all my dresses during winters because I get really confused on how to wear them in winters.

  6. I love wearing dresses in the winter! I love the moto jacket look and usually I wear a coatigan over them too!! Plus leggings and tights are my go to in the winter!

  7. I love how you styled your dresses in different ways to stay warm in the winter. As for me, I love wearing sweater dresses with tights and OTK boots to stay warm❤️

  8. I am a huge fan of dresses year round and these are such great ideas! I love the vest over the jersey dress. So cute!

  9. I’m also petite and dresses are my favorite go-to as well. OTK boots have been my secret so far this winter. So many cute looks!!

    Xo
    Jenny

  10. Staying warm doesn’t have to be bulky and unpretty. This post definitely about that. I love how you played around with classic colors and prints and also how you showed us the variety of styles you can pull off, without compromising being stylish. I absolutely love them all, but my favorite is the pastel; so charming and very feminine. Thanks for the inspiration!

    ~ xo Sheree
    PoshClassyMom.com
    http://poshclassymom.com