If the thought of wearing anything other than thick jeans or warm, fleecy leggings during the winter months leaves you feeling cold, then the warm winter dresses in this article may just change your mind.

If you usually push your dresses to the back of your closet when the weather turns cold, think again. Below, you’ll find plenty of warm knits, long sleeves and high necklines to make sure you stay warm all the way through until spring as well as inspiration for your winter dress outfits.

I know that you’re likely to have a little black dress in your closet already for evening events, so this article concentrates on daywear winter casual dresses – the kind of dresses you can wear with your ankle booties and a winter coat for everyday, casual wear.

What to look for in a winter dress

While summer dresses tend to be made in flimsier, floaty fabrics, those thin layers aren’t going to keep you warm during the cold months.

When looking for warm winter dresses, keep an eye out for knitwear styles, such as sweater dresses, along with long sleeves and possibly higher necklines to keep the chill at bay. Thicker, insulating fabrics or dresses with lining will also help you to stay warm.

Essentials for your winter style dresses

Melissa wearing a warm winter dress outfit | 40plusstyle.com

Before thinking about the best winter dress for you, I’d advise investing in some thick-high-quality tights, as well as a versatile pair of winter leggings that you can use to add extra warmth.

Add a pair of ankle booties to your warm winter dresses, and you’re good to go!

Melissa (above) makes sure she stays warm in her warm tights and booties; layering a cozy cardigan over her dress.

Check out this printed dress that you can wear with this similar cardigan, tights and booties.

HUE opaque tights with control top | 40plusstyle.com

HUE opaque tights with control top

The best winter dresses for women to choose

Now, let’s move on to some of the best choices in stores now for the upcoming winter season. Choose your favorite!

Winter wrap dress

When looking for the best warm winter dresses, a wrap dress is flattering for all figures. Plus, the v-neck creates an elongating effect and looks great for most body shapes. Depending on your height, the Vera Moda dress (below) is likey to fall two or three inches above your knee, making it a good option to wear with leggings or thick tights.

Warm winter dresses - VERO MODA tie waist sweater dress | 40plusstyle.com

VERO MODA tie waist sweater dress

Turtleneck dress

Jas wearing a winter sweater dress with a moto jacket and boots | 40plusstyle.com

If you want to make sure you keep your neck warm during the colder months, you can always add a scarf. But, a turtleneck is another great option.

Jas (above) wears a studded moto jacket over her gray turtleneck dress.

Recreate her outfit with this similar sweater dress, moto jacket, tights, tall boots and sunglasses.

Warm winter dresses - VERO MODA turtleneck sweater dress | 40plusstyle.com

VERO MODA turtleneck sweater dress

Dresses for the winter season: Leather dress

The winter season is a great time to experiment with different textures and fabrics. While leather often doesn’t feel comfortable during the summer, it’s perfect for winter.

You could layer a turtleneck top under this leather dress from COS (below).

Warm winter dresses - COS belted leather dress | 40plusstyle.com

COS belted leather dress

Fit and flare sweater dress

As with all of your dresses, you can choose a style which suits your body shape. A fit and flare style, like the one below from Eliza J is a beautiful option for the hourglass or pear shape.

Warm winter dresses - Eliza J fit & flare sweater dress | 40plusstyle.com

Eliza J fit & flare sweater dress

Best winter dresses: 2-in-1 dress

A big trend this season is to wear a cozy sweater over your slip dress. All Saints has made it easy for you by putting the two together in the two-piece set below.

Warm winter dresses - ALLSAINTS two-piece sweater & dress | 40plusstyle.com

ALLSAINTS two-piece sweater & dress

Blouson sleeve sweater dress

A major trend for the past couple of seasons has been to choose sleeves with some volume. If you like to create an impact, a blouson sleeve dress like the one below from Staud could be perfect.

Warm winter dresses - STAUD midi sweater dress | 40plusstyle.com

STAUD midi sweater dress

Winter dress ideas: Long sleeve dress

Warm winter dresses to keep you cozy and stylish no matter what the weather | 40plusstyle.com

Opting for long sleeves will keep you warm when the weather turns cool.

Bev (above) shows that a neutral outfit can make a big impact when it comes to choosing your warm winter dresses and accessories.

Steal her look with this similar long sleeve dress, coat, boots and handbag.

Warm winter dresses - COS turtleneck dress | 40plusstyle.com

COS turtleneck dress

Button down sweater dress

Buttons have been a major feature on summer sundresses this year. You can get a similar style for winter with the button-down dress below from Fraiche by J.

Fraiche by J button ribbed midi dress | 40plusstyle.com

Fraiche by J button ribbed midi dress

Long winter dresses

Maxi dresses are often a stylish option for summer. You just need to add a pair of sandals to make an impact.

For winter, you will need to think about the weather. You don’t want the hem of your dress to get wet in the rain or snow! However, add a pair of boots (heeled if you need to) and a moto jacket and your maxi will still be perfect for the colder months. Look out for a maxi with sleeves like the option below from Amazon.

DEARCASE maxi dress | 40plusstyle.com

DEARCASE maxi dress

Long sleeve shirt dress

A shirt dress is always a versatile option. You can wear as a dress or you can unbutton and wear as a duster jacket over your jeans or pants and t-shirt. I’d let the strong pattern on the Chi Chi London shirt dress (below) do the talking and wear simply with a pair of black opaque tights and knee-high boots.

Chi Chi London geo print shirt dress | 40plusstyle.com

Chi Chi London geo print shirt dress

Short winter dresses

Emma wearing a mini sweater dress | 40plusstyle.com

Even if you’ve given up your mini dresses, you may still want to think about a shorter option for winter. You could wear as a tunic over your leggings or with skinny jeans.

Emma (above) wears her short sweater dress with thick tights and boots.

Check out this similar sweater dress, tights, boots, bag and sunglasses.

The wrap style below features ruching and a v-neck, making it a flattering choice to wear over your leggings.

Fraiche by J sleeve ruched faux wrap mini dress | 40plusstyle.com

Fraiche by J sleeve ruched faux wrap mini dress

Long sleeve wrap dress

Another wrap option for you below with long sleeves! This Vera Modo wrap dress could easily be dressed up or down.

VERO MODA wrap dress | 40plusstyle.com

VERO MODA wrap dress

Long sleeve print dress

You can add a pop of bright color, even on the darkest days, with the print dress below from Marks & Spencer.

Marks & Spencer satin floral print midi shirt dress | 40plusstyle.com

Marks & Spencer satin floral print midi shirt dress

Winter day dresses: Corduroy dress

A tactile, warm fabric option for winter is corduroy. While you may expect to find corduroy shirts or pants during the winter season, the Boden shirt dress (below) brings an unexpected way of wearing this fabric.

Boden corduroy shirt dress | 40plusstyle.com

Boden corduroy shirt dress

Animal print dress

Deborah wears an animal print maxi dress | 40plusstyle.com

Animal print is a stylish option for any season.

Deborah (above) wears her animal print maxi with sandals. But you could always winterize the same style with ankle booties.

Steal her look with this pair of sandals from Birkenstock, and wear it with this similar maxi dress, necklace and earrings.

You may also like the midi style (below) from Reformation, which would look lovely styled with tights and black knee-high booties.

Reformation print midi dress | 40plusstyle.com

Reformation print midi dress

Amazon knitted wrap dress

The wrap waist and blouson sleeves on this tie-waist dress (below) could be figure-flattering for many figures. This dress is very short though, so you’re likely to want to wear with jeans, pants or thick leggings – styling it as a long tunic rather than a dress.

R.Vivimos tie waist winter dress | 40plusstyle.com

R.Vivimos tie waist winter dress

Boden jersey dress

If you love prints which are a little different, Boden is often a good place to look. The pattern on this wrap style gives it a bohemian feel. It does have a very low v – so you may want to wear a camisole underneath.

Boden dress | 40plusstyle.com

Boden dress

Black slit dress

Cassie wears a black sweater dress | 40plusstyle.com

For a winter version of the little black dress, how about choosing a knit dress with a slit on the leg. You can always add thick tights depending on how much leg you want to show.

Cassie (above) styles her black dress casually with sneakers and a denim jacket.

Recreate her outfit with this similar black slit dress, denim jacket, sneakers, belt bag and sunglasses.

French Connection mock neck sweater dress | 40plusstyle.com

French Connection mock neck sweater dress

Red sweater dress

Simple, stylish and figure skimming rather than figure hugging, the Halogen sweater dress comes in a choice of neutrals which have contrasting trim around the neck and wrists. I prefer the simplicity of the red option (below).

Halogen sweater dress | 40plusstyle.com

Halogen sweater dress

Tie dye midi dress

If you want to add a bit of edge to your winter dress, how about choosing a tie-dye option. The waistine is pleated to flatter the figure. You could wear with booties and a moto jacket for a rock chick style, or add a blazer and heels for a more refined look.

Fraiche by J tie dye pleat midi dress | 40plusstyle.com

Fraiche by J tie dye pleat midi dress

Winter dresses with boots: Black and white dress

Karen wears a zebra print dress | 40plusstyle.com

Monochrome never goes out of style. This season, there are plenty of zebra print options on the high street.

Karen (above) wears her zebra print with black booties and a long cardigan.

Check out this similar dress, cardigan, booties and sunglasses.

Baum and Pferdgarten lng sleeve midi dress | 40plusstyle.com

Baum and Pferdgarten long sleeve midi dress

Winter dress outfits: What to wear with your warm winter dress

Lucie wears a red sweater dress and pink faux fur coat | 40plusstyle.com

Now that you’ve chosen your favorite winter dress, what should you wear with it? Tights and leggings will keep your legs warm. If you choose leggings, you could wear a shorter dress style.

You could either wear a moto jacket over your winter dress or choose a coat which is longer than the hemline of your dress.

Team with booties or knee high boots.

Lucie (above) wears a coat which sits just below her dress and adds stylish knee-high booties.

Recreate her outfit with this similar dress, coat, suede boots, tights and handbag.

I noticed there are a lot of gray and beige sweater dress options on the high street this year. So, if you do choose one of these neutrals when you choose your warm winter dress, you may also like to take a look at the best colors to wear with gray and how to wear beige without looking frumpy.

Continue reading:

  1. The Best Dresses To Hide Your Tummy
  2. The Best Dresses With Sleeves For Women Over 40
  3. How To Wear Tunics Or Short Dresses With Pants

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Warm winter dresses to keep you cozy and stylish no matter what the weather | 40plusstyle.com

Feature image by Bev


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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