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How To Wear Skirts In Winter – Easy Style Guide

Skirts make a great addition to any cute and stylish outfit and can create a casual look that also feels free and spacious to move around in.

They come in a range of sizes and lengths making it easy to pick out an option that you know would fit your personal style best.

How to Wear Skirts in Winter

With a range of colours, patterns and designs they are some of the most popular and customisable clothes on the market and are a lot of fun to experiment around with to find the particular fit you’re looking for.

Winter can get in the way of this and be quite annoying with its cold bustling winds and freezing temperature making skirts a bit tricker to wear since they lack the necessary warmth and length for the colder months.

If a skirt is something that has become a major part of your style then never fear, you can still wear them in winter and look both comfortable and trendy doing it, you will just need to consider some workarounds that will allow you to style your own outfits, while also keeping comfortable and warm in the harsher months.

Is It Okay To Wear Skirts In Winter?

While it can be a little chilly if you don’t take certain precautions to keep a bit warmer, skirts definitely can be worn in the winter and can look great when paired with some other winter clothing.

Longer skirts are usually more recommended for winter months than short skirts which can sometimes look a bit odd and feel very chilly.

There are many ways you can mitigate this issue however by pairing other clothes with your outfit to give you that extra bit of warmth but not taking away from your original style, and instead giving a cosy winter look.

With such a range of these options it is definitely worth having fun and experimenting with different looks you can rock all through the winter.

Tall boots for example are a great choice as well as another layer under a skirt, or if you want to style something on the upper body, you could even try a long chic coat or a chunky scarf and jacket for extra warmth.

Below we have listed the most stylish clothes you can pair with skirts in winter months to keep you warm and feeling confident for each and every skirt type, so you can find the right fit that matches your own fashion taste.

1. Long Coat Or Trench Coat

Great for the winter months with any outfit, a long formal coat or trench coat reaching to the knees are often made of thick woolly material that will both keep your upper body and your legs partially warm.

This option won’t just keep you comfortable however, when matching a long coat with a skirt it actually is a great fashion statement, creating a very sophisticated look and one that can be both formal when needed, or just a cute and casual outfit for those chillier days.

Try a grey or nude colour coat to really give off a cosy and seasonal feeling from your jacket of choice.

2. Fleece Jacket

An option that is more casual and fits on the upper body to keep you toasty but still looking stylish is a fleece jacket. Their chunky design mixed with heat retaining material will make up for any heat lost by a skirt.

In a range of colours, patterns and designs, you can really have fun with this suggestion and seek out a jacket that would perfectly match your outfit and skirt.

The jacket does not have to be too long, only going down to the waist is fine because the material is what will keep you warm and cosy.

To finish this outfit, try fitting it with a thick scarf, and if you want to make it extra vibrant for the winter season, look for either a grey or multicoloured design.

3. Thick Sweater

Sweaters are another great upper body option that will help make up for the heat lost in your legs.

The sweatshirt should be long sleeved so that you can protect your arms, however the rest can be up to you depending on how spacious and free flowing you want it to be, along with the specific material and colour.

Sweaters can be a great option for the sunnier seasons however they are also a good choice all year round being the perfect clothes to make a fashion statement while keeping comfortable.

This is especially the case because of how many varieties of sweaters are on the market with everything from material, to length and colour being drastically different in each one.

We would recommend matching some darker skirts such as grey and black with a light pink sweatshirt to create a warm, friendly and incredibly cute fit suitable for most occasions.

4. Leather Jacket

Not even a leather jacket is out of the question, and if you have one stashed away from the cooler seasons, it might be time to try it out in the winter months along with a skirt.

This can be a perfect option for days that are not too cold but just a little breezy, and is a quick and easy option to throw on to have that little bit of extra warmth when paired with a skirt.

Black and brown leather often looks the best in the winter, and you could even try also wearing a thick woolly scarf to give off a very comfy and sophisticated look that’s great when you have to travel a decent distance or are out and about the town.

5. Bodysuit

This may not have been the first choice to pop into your head, however bodysuits are actually a perfect option to exchange for a regular top to ensure you stay warm.

Bodysuits are much longer than a regular top and will cover much more of your body, this can protect your tummy and provide a lot of added heat simply by wearing it.

The thin designs of most bodysuits will not add any chunky layers to the skirt and can easily be tucked under to create a fit that looks casual and effortless, and is sure to keep you safe in colder conditions when the weather is against you.

6. Legging Or Thermal Tights

Perhaps the most popular option on this list, a pair of leggings or thermal tights are an easy way to keep your legs warm without adding too many layers and making the outfit too cumbersome to move around in.

They instead look sleek and are a very stylish option to match with a skirt in the colder months, however to really make sure this outfit stands out, try making sure that the colour of the skirt is a colour that will merge well with both your skirt colour and shoes.

A great recommended option that will keep you comfy and confident in your look is matching a rose red skirt with black leggings/thermal tights and black heels or regular shoes.

This look is incredibly eye-catching and will have fashion enthusiasts wishing they could replicate it for how well it mixes a business look with a fit that could just as well work casually when visiting friends or family.

7. Tall Boots

An excellent option to keep mainly your legs and calves warm, knee high boots are not just an excellent choice for the spring, but for the winter time they work just as well being incredibly comforting and easy to move around in while privind that extra bit of comfort.

The beauty of tall boots is how versatile they are, whether it’s a windy day where you will need to wrap up warm, or if there is just a hint of a chill in the air, knee high boots will work for either occasion.

They can also be worn over leggings and tights making them incredibly cosy, or if that isn’t required you can still simply sneak some long socks underneath the boots to still add a good amount of cosiness.

8. Ankle Shoes

Ankle high boots for many are the go to shoe option for the winter, they are fun, fashionable and warm.

They feel great to walk around in and can be great for both formal and casual occasions, so always consider them with a skirt if you’re going to a gathering or social event.

They also have the added bonus of looking great with virtually all skirts. Whether it’s a full length skirt or a pencil skirt, ankle high shoes with their smart appearance and thick interior makes them the perfect option to stay warm and stylish in the winter when matched with a skirt.

9. Layer A Skirt

Adding a hidden skirt under your original one can add an extra layer of comfortability without exposing your outfit.

All you need to do is make sure the helm of your top skirt covers the helm of your under skirt to create a seamless finish.

Also, make sure the layered skirt is of a slightly thinner material so that it is not too bulky and isn’t pressing on your waist too much to avoid it being too cumbersome to move in.

To make sure the layered skirts are even harder to see and easier to move in, try opting for the outer skirt to be longer down to your knees or below, and choose a layered skirt that is a mini skirt to just add that extra hint of warmth without looking silly.

10. Try A Longer Skirt

This may seem like an obvious recommendation, however if you already have an outfit ready including the top and shoes and just want to change something about your skirt to create some warmth but still look trendy, a longer skirt can be an incredibly easy option to do this.

Try and pick out a skirt that extends somewhere between your mid calf and top of the foot, or even one that can extend to ankle length if you want to cover your legs entirely and keep them heated.

Just make sure a skirt is no longer than this otherwise it can end up getting stained, wet and muddy and can be a bit troublesome to walk around in on chillier and rainy days.

The right longer pair however will allow you to feel free and comfy alongside feeling stylish.

11. Accessories

Never forget that even the smallest accessories can be a big part of an outfit and add an extra bit of colour or personality to a fit.

A chic scarf is an easy and cosy option that can come in a multitude of colours to really make your outfit pop.

A pair of leather or suede gloves will also go great with most looks and is an excellent way to retain some of the heat lost when wearing a skirt.

A beanie or knit hat is also an excellent option that you can colour match with the rest of your outfit and is an easy accessory to try on and see how it fits.

How To Wear Different Kinds Of Skirts In The Winter

These styles will work great for any length of skirt and will be sure to keep you warm while still looking stylish, however for particular suggestions for each specific kind of skirt, here are a few general pointers towards styles that would work great.

1. How To Style A Mini Skirt

Mini skirts are probably the trickiest skirt to get right in the winter since because of the way they are designed, they don’t really allow for any warmth for most of the legs and are more so worn in the summertime and spring.

This is not to say they can’t be worn in the winter time however, they certainly can, you will just want to also style some other clothing alongside them so you can make sure you don’t end up getting too cold when outside.

The best option for mini skirts is tights and leggings, however do keep in mind that sheer tights may be a bit too thin and won’t keep you much warmer.

Instead try seeking out a pair of wool tights or leggings to ensure the material keeps you warm while still looking stylish and festive.

Mini skirts can also look great when fitted with either a long sleeved shirt or sweater, topped with a fleece jacket or blazer if you want something a bit more formal.

These long sleeves and layers on the top of the body will be needed to make up for the lack of heat in the tights, however they still mesh really well and create a colourful and warm outfit style perfect for those chillier days where you want to keep warm, but still want to rock your favourite mini skirt.

2. How To Style A Pencil Skirt

Pencil skirts can be worn as both a casual and formal option. For a more casual look, a pencil skirt can look very fun and cosy when paired with a comfy cropped jumper or sweater and heeled boots to create a look that is relaxed but still eye-catching and stylish.

If you are looking for a more formal style, you can try pairing a pencil skirt with some black tights and heels that will help retain heat, along with a blazer to create a sophisticated and smart look that will keep you from getting too chilly.

3. How To Style A Longer Skirt

Long skirts will keep most of your legs warm in the winter time and are perfect for an all in one option that you won’t have to add much to in order to stay heated while looking great.

Try and match a long skirt with some colourful options to create a fun and festive look that will be incredibly eye catching to onlookers.

A fitting top or cropped jumper in a nude pink or beige can be a great option that is not too bright, but strikes a perfect balance between casual and professional.

You can really finish this outfit off in style with a pair of heeled boots in a colour of your choice, brown and black tend to be the best options for a smart look that will be sure to keep you nice and toasty when it’s cold.

4. How To Style Summer Skirts

You may have a summer skirt from a few months ago that you’ve stashed away hoping to bring it out for next summer, however these can still be worn in the winter and can make quite a fashion statement with how colourful they are.

Summer skirts can be quite short so try again to pair them with wool tights and leggings for a stylish and warm fit, however also try to keep in mind colour coordination as summer skirts tend to come in a wide range of bright colours for the summer time.

A great way to do this is simply look for summer skirts that are slightly darker or at least have darker shades of their colour so that they can mix well with the dark black of leggings and tights as well as your top.

A smooth dark red or brown colour for example can create a striking pairing with some black leggings that oozes style but also ensures your legs don’t end up getting too chilly.

5. How To Style Denim Skirts

Denim skirts with their smooth design and darker colours are also very viable for the winter time when matched with some woolly tights or leggings because of how short they can be.

The best thing about denim skirts is, just like a denim jacket and jeans, they can essentially be matched with any colour.

A free flowing yellow sweater will match with a denim skirt as well as a red floral shirt, so it grants you a great amount of customisation so that you can create a style exactly to your liking.

Add some accessories such as a thick belt, coloured purse or heeled boots to really finish off this outfit and create a cosy look that can keep you comfortable no matter how chilly it gets.


Finding styles that can incorporate a skirt in the winter can be a little tricky, however it doesn’t have to be, just like the spring and summertime winter is a new window in the year to have fun experimenting and trying out new styles to fit with the season.

While skirts are more so seen in the warmer months, never be afraid to try out different combinations of clothes to find a style that can look festive and appropriate for the winter without leaving you cold when the weather gets a little chillier.

Jenna Reign
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