How To Wear Dresses In Winter & Don’t Look Frumpy

We usually start wearing just sweater dresses in winter, but it does not have to be that way. I wanted to share some ways I like to wear all my summer dresses even in winter while staying cozy and looking stylish. 

I hate packing away my summer pieces because let’s be honest, while people talk about Capsule wardrobe, I intend to use my whole wardrobe every season. And I am specially not ready to part ways with the pretty dresses I bought in summer. 

And you don’t have to either. There is so many ways to layer them and look stylish as well. 

Your dresses jut does not have to bohemian, or special occasion dresses, all this hacks that I use, can be tried on any style of dresses with some basic style principles to look really stylish.

Over the Years I have learned that what is important in a dress is the woman wearing it

              – Yves Saint Laurent

Layering For Style

Layering is the only way to stay warm usually, but proper layering can make the biggest difference in your overall look. 

I have to be honest, it took me a lot of time to finally figure out the proper way of layering for my body and to create a cohesive style that looks effortless and chic.

Oversized with Structured

This is the easiest way of layering any outfit. Always layer something oversized with something structured. I love pairing dresses with oversized sweaters, but I usually pick dresses that are more structured around my waist so that It gives an appearance of a skirt when paired with a cropped sweater. 

Now, if you want to pair a longer sweater with a dress, it can also be styled in a chic way by adding a belt. I shared a way of doing that in the post about styling Oversized sweaters.

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Dress // Sweater (Similar) // Boots // Bag (discounted preowned)

Mixing Sleeve Styles

This is specially fun when you have a short sleeve or a long sleeve dress and you want to create a layering style to shoe the dress and not hide it with a chunky dress. 

I am so glad that vests are back in style and they are not just for fall or spring. Vests actually make it easier to layer where you might not have to take off your layers at all since you are not creating a really warm outfit, plus you can add more layers without creating that sleeve bulge which is what puts us off from layering to begin with. 

This you might already know, but you can layer a slip dress above a thicker sweater and most of the time it looks the best with cowl neck or turtlenecks because they add a structure to the really delicate straps of the dress.

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Not So Obvious Layering

With Dior’s vintage runways, this style has kind of made a comeback where turtleneck or mock neck blouses were worn inside dresses to create a layered victorian neckline. 

I absolutely adore that style, and it can easily be created with a turtleneck sweater underneath a deeper neckline dress.

This specially works with v-neckline or round neckline. And your neck looks elongated. I usually don’t have a really long neck, but in winter I wear a lot of turtlenecks that makes my neck appear longer.

The trick is to add something that is more structured around the waist, or has a bit of tailoring, compared to wearing something flowy. Otherwise, it might look too bulky.

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Dress // Turtleneck // Boots // Bag (Sold Out)

Cozy Layering

An obvious layering that we all do is adding tights to your dress to stay chic. I love wearing opaque tights with dresses because I want them to just blend in compared to standing out in the entire outfit.

This way your dress is more highlighted as well and it just looks a bit more sophisticated for me.

Proper Footwear Pairing

With dresses, I always felt like tall boots look the best, don’t you think so too? They are the perfect length that if the weather permits you can skin the tights, or even if you wear them, you can add a but more sophistication to your outfit with the right boots.

I always love wearing tall boots with pointy or square toe boots which was 2020’s popular trend. While I do like round toe boots, they tend to look way more causal and not so flattering with a pretty dress.

You can either match the boots with your tights or match wit h another piece of accessory you are wearing to create a cohesive look. If I don’t find anything this matching my boots, I prefer to match it with my handbag, and that is one of the biggest reason sometimes that I buy shoes to match my bags, because its an easy way of creating a cohesive look.

Length Matters

This is really important if you are petite, because dresses can cut our heights very easily. If you are short, and you wear a short dress, you appear even more petite.

But if you wear a maxi dress you don’t look as short. If you want to wear a shorted dress, try to wear ankle boots with pointy toes.

Now, I know that if you live in really cold climate, this is not really feasible, in that case, boots matching the color of your bottoms will help elongate your entire silhouette. 

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The Color Trick

I love wearing colors in general all around the year, but in winter I specially focus way more in adding colors to my outfits to make them look vibrant and luxurious. 

And this is my favorite way of wearing dresses as well. I love pairing colorful dresses with my outerwear to create a vibrant and fun look that I also love wearing.

Some key ways I add colors into my dress outfit.

Monochromatic Look

Before you runaway from this post reading about colors, I wanted to give you the easiest way you can add colors to your outfit. 

Create a monochromatic look with your dress and your outerwear piece. It can be done in many ways. If you are wearing a sweater on top of a dress, match that with a similar tone of outerwear.

You don’t have to match the entire shade, as long as the color is in the same color tone, you should be good. 

Colorful coats are like my weakness, plus the options with them increases many fold and not just creating monochromatic looks.

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Print & Pattern Mix

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This is specially easy because in general a lot of our dresses are printed for spring summer, so adding that with a solid outerwear, makes it look really chic as well as wearable. 

And with a print, you can easily experiment with different colors because usually prints are multi colored in any dress.

You can also add colors that would compliment with something printed like in this outfit here, I am wearing a red printed dress and green coatigan that looks great together. 

But don’t add anymore colors than that. A good rule is to keep your colors in any outfit to a minimum of 3. Anymore, can create a body outfit and it does not look the most flattering. 

But honestly some people can still pull it off, but I have never been able to, so I would recommend against it.

Accessorize the Dress

I have always been a minimal kind of a person, but as I am getting older, I have learnt to not just layer with pieces but also to experiment with accessories. 

And the fun part is in winter we can get away with so many accessories. I love wearing patterned scarves with a solid dress and the other way round. And scarves are a great way to look chic and keep your neck warm while doing that. 


Winter Accessories

I have love wearing hats during winter, and usually beanies are my favorite head gear. And you don’t have to wear them with something casual. You can also add them to something fancy to create a balance. 

If you don’t like beanies, bucket hats are also popular way to stay warm and look stylish.

Power of Gold Jewellery

I love wearing layered necklaces, that look so chic and add a pop of color even if you are wearing some dull. They also make your outfit look chic and incorporate a touch of luxury. 

And Specially in winter you can easily get away with wearing chunkier necklaces if you didn’t like them in summer.

Colored Accessories

This is something you might have noticed, but I love colored sunglasses in general and its specially easy to wear in winter because the sun is barely out and it looks so chic.

I think they are such a great retro trend that will stick with me for years. 

I hope this post helped you to reconsider wearing your dresses in winter as well. I also have a YouTube video where I have shared some more ways you can style your dresses.

If you have some tips for me and our fellow readers, I would love to know. Please share and spread the love. And Until then, Happy Styling!

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