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How To Wear A Dress In Winter - AnyTime Dress

Wear A Dress In Winter 

It could be tempting to swap out your dresses for the cosiness of heavy sweaters and slacks as winter's chill sets in. But even in the coldest months, you can show off your style and grace by wearing a dress with a little imagination and thoughtful layering. We'll look at how to dress for winter in this guide without sacrificing style or comfort.

How To Wear A Dress In Winter
How To Wear A Dress In Winter 

You may still wear dresses in the winter, despite the chill in the air! Although you might not think of dressing up for a dress during chilly weather, there are many holidays, festivities, and other festive occasions that call for it. I've got fashion tips for wearing dresses in the cold right here. 

You'll be longing for dresses all winter long after reading this style guide. Thus, you will now have a couple dresses in your winter collection if you don't already have any. 

Is a dress appropriate for winter wear?

Yes, you may wear dresses in the winter. The trick is to pick styles that are appropriate for the weather, like jumper dresses. Alternatively, you might stick to a few summer dress styles throughout the winter and dress warmly by wearing tights, boots, and layers of clothing.

There are several dress styles that will make you look put together and stylish while remaining appropriate for the winter weather, even though the temperatures are dropping. Continue reading to find out more! 

Opt For A Sweater Dress

Christal is dressed in a black cardigan, long black boots and a grey jumper dress.

The ideal approach to wear a dress in the winter is to choose a style that is appropriate for the weather, such as a jumper dress, knit dress or ribbed dress. Since sweater dresses are the epitome of the cold weather dress, you can't go wrong with this essential piece for your winter collection.

Opt For A Sweater Dress
Opt For A Sweater Dress

Whether you choose wool, cashmere or cotton fabrics, or mini, midi or maxi length styles, there are an endless number of jumper dresses to pick from. 

To add extra complexity and a warm layer to this ensemble, I paired a fitted black cardigan with a midi dress made of ribbed knit. I've chosen to cover the remainder of my legs with these stunning Poppy Barley Toujours knee-high boots because the dress is shorter, ending at my knees.

Graphic showing how to wear a summer dress in the winter.

How To Wear A Summer Dress in Winter

Alternatively, here's how I suggest you use your summer dresses throughout the year, even in the cold!

How To Wear A Summer Dress in Winter
How To Wear A Summer Dress in Winter

Tip 1: Dress in a dress with a floral design to layer over Christmas.

Christal is decked up in a dress with a floral motif, a white jumper on top and towering black boots. In addition, she has a leather jacket on.

I'm dressed for this look in a traditional floral midi dress for spring and summer, complete with flowy sleeves and a pretty silhouette (the dress is from Evernew, but it's sold out; I've linked something similar above). My summer dress becomes an outfit I can wear throughout autumn and winter with the help of a jumper. 

To achieve the style, just wear a midi-length summer dress with a warm knit jumper layered over it. To give the jumper more shape, tuck it in with a 'invisible' belt (see how to wear a jumper over a dress here).

Remember the influence of shoes and outerwear as well! I finished the outfit by grabbing a black shoulder purse, throwing my Quince leather jacket over my shoulders, and wearing my knee-high boots.

Wearing gear that is suited for the winter months adds another layer of warmth and polish to your ensemble. When paired with a trench coat, wool coat, or jacket, your summer dresses will instantly feel more suited for the colder months. 

Tip 2: Wear a long-sleeved top underneath a black slip dress and black Chelsea boots to layer beneath Christmas.

Layering is the key to dressing stylishly in the winter. While it's common knowledge that layering over your dress extends its life, you may also layer underneath your dress come wintertime.

Sleeveless or slip dresses are the ideal foundation for a lightweight turtleneck or thin long sleeve, like the one I'm wearing here. It won't seem strange or add ungainly heft to the ensemble if you wear it with a lighter top.

Using a matching long-sleeved top underneath my black slip dress, I created the illusion that the dress had longer sleeves for this outfit inspiration. In winter, combat or heeled ankle boots look great with maxi dresses, but Chelsea boots are a great option as well.

Put an additional layer of clothing, such as a jacket or vest, on top to trap even more warmth. 

Woman with a bodycon dress and combat boots during the cold, with a long sleeve top underneath.

Women dressed for winter with a slip dress and lug boots with a long sleeve blouse underneath.

Tip 3: Wear tights

What other winter dress code is there? Try wearing tights. Wearing thick pantyhose or tights with dresses that accentuate your lower limbs is an easy way to seem put together.

If you're wearing a shorter dress in the cold, tights are a need. Make sure the tights you choose to wear go with the dress whether you decide for a mini or midi dress. You should use sheer tights with certain gowns. To keep your legs toasty, however, opt for opaque tights with fleece inside if at all possible.  

Even if they are hidden, tights can be used with gowns that are longer in length. For additional coverage when wearing knee-high boots with a long dress, consider warm tights or even leggings underneath. 

Tip 4: You Can Embrace Tall Boots

Christal wore a black jumper, black boots and a floral dress.

The simplest way to elevate your summer dress for winter is to swap out your trainers and ankle boots for knee-high boots. Not only do these stylish, taller boots update any dress for the winter, they're also one of the biggest trends in fashion. A win-win situation for when you wish to dress elegantly and stylishly in the winter.

You can wear knee-high cowboy boots, block-heeled boots, or flat boots for informal outings where you'll be walking a lot. High-heeled, pointed-toe boots are a terrific choice for a dressier look; they should ideally be made of leather, suede, or embossed leather. 

For this outfit, my choice is a pair of knee-high black leather boots. The black boots also give it a more wintery feel by providing a striking contrast to the summer dress with its flowery pattern.

Tip5: Steer clear of summer and neon fabrics.

Christal's illustration illustrates the wrong wintertime attire code.

We've shown you that you don't have to give up on all of your summertime favourites just because winter arrives! You still shouldn't wear some dresses, though. My best advice for selecting a summer outfit that works well for winter use is as follows:

Avoid looking out of style by avoiding tropical designs and blatantly bright colours.

Opt for muted colours and delicate floral designs instead; these complement the winter months better. Light hues like milk and white can still be worn by combining them with dark hues or suede and leather accessories.

Steer clear of dresses made of sheer, crochet, linen, or cotton gauze; these airy materials won't keep you warm during the winter. Cover-up dresses and sundresses that appear unfit for a beachside holiday are not appropriate. 

Your summer garment is ready to be worn in winter if it meets these requirements!

What to wear with a dress to not be cold?

Here are some items you can wear in the winter to stay warm while wearing a dress:

Cover your outfit with a cosy knit cardigan or jumper.

Put on tights underneath your dress; thick or fleece-lined tights work best.

Underneath your dress, put on a lightweight turtleneck or long sleeve top.

Include warm gear such as trench coats, long wool coats, and leather jackets lined with shearling.

Put on over-the-knee, knee-high, or ankle boots.

I hope these useful suggestions for dressing in dresses for winter have been enjoyable for you. This style guide demonstrates how you may wear dresses all winter long and be comfortable by layering appropriately.

Give your summer dresses a second chance at life by styling them for the upcoming cooler months rather than shoving them away for the season. You'll be shocked at how well they match the rest of your winter attire!


Dress season doesn't have to end with winter. You may stay cosy and fashionable while looking confident in your favourite dresses by paying close attention to fabric choices, layering strategies, and well-chosen accessories. Be creative in your embrace of the season and let your winter attire embody the grace that is impervious to temperature changes.

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