How to Wear a Short Dress: Winter Style

One of my least favorite parts about the shifting of seasons to cooler weather days is saying goodbye to all of my favorite short dresses. I don’t want to freeze, but I also have so many short dresses that I love and that I’m not ready to part with as winter comes around. That was why I was determined to find ways to make a short dress winter-ready, and I’m thrilled to say that I’ve come up with a list of tips and tricks for you!

If you want to keep wearing your favorite short dress all winter long, don’t fret – there are ways to make that happen! It just takes some creativity and layering to make sure that you stay warm while staying stylish all the while. Keep reading for all of my best tips and tricks, as well as my favorite pieces to add to your closet to make styling a short dress in the winter easy and low-stress. Trust me – you will soon be pulling your short dresses out all winter long!

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HOW TO MAKE A SHORT DRESS Winter Ready

It can be hard to know how to stay stylish during the winter months. When the cold weather kicks in, oftentimes all I want to do is throw on my warmest sweater and call it a day. Function can be quick to win out over style when the temperature begins to drop, but we can’t abandon our love for style just because it’s cold out! All it takes is getting a little extra creative, and before you know it, you’ll be rocking a winter look that keeps you warm and cozy while also being super cute. You just need a little practice!

Winter doesn’t mean that you have to pack up your favorite mini dress and only wear sweater dresses until spring comes again. You have more options than you think you do – you just have to learn the best layering techniques so that you don’t freeze, even at less-than-preferable temperatures. It is possible! And I’m so excited to show you how today. From sweaters to tights, scarves to boots, hats to gloves and beyond, there are so many different ways to make your short dress winter ready, no matter how casual or fancy the occasion.

Women’s fashion can be hard, especially in the wintertime, but it doesn’t have to be. Keep reading to learn how to take your winter dress looks to the next level!

WHEN TO WEAR A Short Dress IN THE WINTER

You might be wondering: when is the best time to wear a short dress in the winter? Under what circumstances should you pull out your favorite short dress despite the freezing temperatures?

The answer is more a matter of personal preference than anything. If you just need to learn how to style a short dress in the winter in a pinch, this guide will have you covered. But it also will come in handy if you really love short dresses year round and need to learn how to style them for everything from a coffee date to a wedding. The occasion is really irrelevant – the same rules apply no matter what.

SHOULD I WEAR A Longer Dress INSTEAD?

With these tips, there’s really no reason to wear a longer dress – I will show you exactly how to style your short dresses for the winter season so that you stay warm and feel stylish. However, there’s no reason to shy away from dresses of different lengths throughout the season as well. Maxi dresses and midi dresses can look great in the winter as well, and many of the same styling tips that I discuss below can be applied to different dress lengths as well. Style is a very personal thing, so at the end of the day, you should wear the pieces that you love. Take the pieces of advice that you love and disregard the ones that you don’t – the most important thing is that you love what you wear!

MY BEST STYLING TIPS TO WEAR A SHORT DRESS IN THE WINTER

When I want to style a short dress in the winter, there are a few go-to tips that I always turn to. These tricks can easily be combined – you don’t have to use just one! Winter is all about layering, and I love mixing and matching different items and ideas to keep my wardrobe feeling fresh. It’s easy to get tired of winter clothes, but by swapping around what you’re doing, you will keep things exciting so that you have fun with your style all winter long, no matter how dreary the weather may be. Keep reading to learn all of my best tricks!

General Tips FOR WEARING A DRESS IN THE WINTER

Wearing a dress, whether it’s a mini dress, midi dress, or maxi dress, in the winter can be stylish and comfortable if you take the right precautions to stay warm. I’m typically one that has avoided wearing short dresses in the winter because of the fact that the brisk wind tends to be harsh on my legs, but over the years, I have changed that up a little and there have been a variety of occasions that I have worn a short dress in the winter. But again, no matter what type of dress you are looking to wear, here are some tips for wearing a dress in cold weather:

PICK THE RIGHT FABRIC

Opt for dresses made of heavier materials like wool, tweed, corduroy, or knit. These fabrics provide better insulation and will keep you warmer than lightweight summer materials.
ADD LAYERS

Layering is key to staying warm in the winter. Wear a long-sleeve or turtleneck shirt underneath your dress for added warmth. You can also add tights or leggings for extra insulation.
EXPERIMENT WITH TEXTURES

Incorporating textured or patterned dresses can add depth and style to your winter outfit. Additionally, textured fabrics can offer more insulation.
WEATHER PROOF THE LOOK

If it’s a snowy or rainy day, make sure your dress is made from water-resistant or waterproof fabric, and carry an umbrella to stay dry.
KEEP YOUR FEET WARM

Insulated socks and warm footwear like lined boots are essential for comfort. Consider wearing thermal socks or adding insoles to your boots for extra warmth.
HAVE LONG SLEEVES

Long-sleeved dresses naturally provide more coverage and warmth than sleeveless or short-sleeved options.
GO WITH DARK COLORS

Dark-colored dresses tend to absorb and retain more heat than lighter colors. If you have the option, go for deeper, winter-friendly hues.

Remember that staying warm is essential during the winter, so don’t compromise on comfort for the sake of fashion. With the right clothing and accessories, you can enjoy wearing dresses in cold weather while staying cozy and stylish.

Top Tips & Style Hacks FOR WEARING A SHORT DRESS IN THE WINTER

Winter coats can come in so many different styles, and it’s so much fun to shop around and select a few staple coats to rotate through your wardrobe all season long. You want to make sure that you have a range of options for yourself – do you have coats for casual events, or just formal events? Do you have coats of varied thickness and warmth to go along with different types of weather? Do you have an option that is waterproof for when the snowy and rainy days of winter set in? There are so many things to think about when it comes to winter weather, and you want to make sure that you have coats that are ready to help you tackle it all in style. Personally, I think that this pink long teddy coat is so cute, but you can also go for a more elegant, sleek look, or wear a classic trench coat.

Tights are great because you can begin incorporating them into your wardrobe throughout the fall, and then in the winter you can make the full transition to fleece-lined tights. They’re the perfect transitional piece as the seasons begin to change and really set the mood to show that you are transitioning your style for the new season ahead. Fleece-lined tights are super insulating, which makes them one of the best ways to stay warm in the wintertime. I love that they come in a range of colors, from neutrals to black, and there are even some fun patterned options as well! Adding a textured pair of tights to your outfit, or a pair with a striped or polka dot pattern adds a unique touch to your outfit that will set it apart.

For days where I want to wear a short dress to something more casual like lunch with a friend, I sometimes like to throw a cozy sweater over my dress just to give some added warmth. This works particularly well with dresses that have a short sleeve as it adds an extra layer. I love the warm and baggy look and think it looks super cute. You also have the comfort of knowing that if you end up in a warm room or the temperature doesn’t end up being as cold as you might have expected, you can easily pull the sweater off and still look great. Bonus points if you snag a dupe of the classic Rory Gilmore sweater – it’s perfect for layering over a winter mini dress!

There’s nothing like a good sweater mini dress in the winter. Chunky knit dresses will keep you so much warmer than a regular dress would, and you can even add an additional layer of tights for extra warmth. Wearing a sweater dress is such a quintessential winter look, and they always put me in a seasonal mood. I love that you can wear them casually or for more upscale events like a date night or dinner out with friends. They’re endlessly stylish and I always get excited to pull them out of my closet when the temperature begins to drop each year. For extra inspiration on styling sweater mini dresses, check out my recent post on styling a tan sweater dress!

Whenever I find myself needing an extra layer in the colder months of the winter, I reach for one of my favorite scarves. I love how quick and easy it is to add a scarf for some additional warmth, and scarves always look cute in the wintertime. You can choose from thick knit scarves (or even make your own, if you’re crafty!) or bigger, draping blanket scarves. The Acne Studios scarf is always a cute and colorful option, and I compiled a list of my favorite dupes if you’re looking to add a few to your closet this season. You can also turn to scarves in more neutral colors, such as black, gray, and tan for staple pieces that will look good no matter what you’re wearing. Trust me – there’s a scarf for every one of your winter dresses!

Tall boots are the perfect addition to a short dress outfit in the winter. Boots are the best winter shoe because they keep you warm whenever you’re wearing a skirt, making them ideal for wearing a short dress in the winter. They work with both bodycon dresses and dresses that have a more flared short skirt, and there are so many different styles of boots to choose from that you never get bored. From thigh high boots to simple above the knee or below the knee boots, there are so many different lengths. You can go with a flat boot or a heeled boot, slouchy or tall chic leather. Black, brown, or a fun color – the world is your oyster! Tall boots are peak winter fashion, and they’re a must for keeping warm when wearing a short dress.

For winter days that aren’t as brutally cold, channel your inner Kathleen Kelly and layer a cardigan on top of your short winter dress. Cardigans add a cute touch to a more casual winter dress, and have a timeless coziness that exudes main character energy. Feel a little more bookish or whimsical with a cardigan over top your winter dress. Cardigans are great for everyday wear, and work especially well in the months that are transitioning between fall and winter and winter and spring.

Do your favorite short dresses have tank straps or short sleeves? Make them look instantly more winter appropriate with a layer underneath. We always think to throw something over as a top layer in the winter, but layering underneath your dress not only will give you some extra warmth, but it will make the look more seasonal. I am a huge fan of bodysuits as they keep heat in really well and fit easily under any piece, and this turtleneck bodysuit from Abercrombie and Fitch is so effortlessly stylish. But if you don’t have a bodysuit, don’t worry – you can still layer! Wear a long sleeved shirt or turtleneck under your dress for added warmth and style. Pro tip: tuck your shirt into a pair of bike shorts under your dress to keep the shirt from bunching up, loosening, or rolling as you go about your day.