How to Wear Shorts in Winter – 20 winter Outfit with Shorts

How to Wear Shorts in Winter. When it comes to winters, dressing up may seem fun but according to a lot of people wearing short dresses is a big no! But many women believe the contrary; they are bold enough to carry shorts and skirts in winters. Girls love affair with shorts runs deep and true, and they can’t bear to pack them away when cold weather hits. But really, there’s no reason to ditch your shorts in the winter. Usually, we tend to hide shorts, once the cold weather hits the door. We used to be taught that shorts are not appropriate for Winter, right? But what if I told you that shorts might look stunning on you? Many fashionistas and models discovered stylish and creative ways to wear shorts in cold season days. They simply don’t believe in restricting themselves to fully loaded clothes, of course they wear clothes to keep them warm but they experiment with even short dresses.

If you want to look chic and stay warm, then wearing shorts can be a perfect idea for you. I personally like shorts for their comfortability and sassy appearance that allows me to show off my gorgeous legs. In this article are compiled the most stylish ways of styling these bottoms during Wintertime. We’ve come up with 20 Perfect Outfits to show you how to wear shorts during winter without sacrificing warmth nor style.

Tips for Wearing Shorts Stylishly in Cold Weather

Winters shouldn’t be a reason for you to ditch shorts. You can style it in multiple ways and wear what you love.
1.Stockings – The good old stockings beneath a pair of shorts are guaranteed to keep you warm and make your look dapper.
2. Knee High Boots – Not only are they a winter essential but pair up excellently with shorts.
3. Long Over Coat – Another item from your winter must haves which compliment dresses, shorts and skirts beautifully in the intense cold.

The biggest problem that might be faced is the covering your legs, as it’s important to keep warmth in your legs up area, that’s why I recommend to always wear tights under shorts to have an extra layer that will save you from unexpected winds. You can add extra warmth by adding tick, soft socks, like over-the-knee ones or chunky mountain alike to team them with your favourite boots or booties.

Today you are going to see various ways how to wear shorts in cold weather, that’s why I recommend to sit back and enjoy these beautifully styled Outfits. Basically, the 20 cute winter outfit ideas with shorts below will help illustrate the point. Keep scrolling for all the seasonal fashion inspiration, and you might actually somewhat maybe be excited for the snowy days ahead when you’re bundled up in these gorgeous ’fits.

20 – Chic Style

If you thought you could only wear a short in the summer, think again, sweetheart! Here is a fantastic example of how you can rock a short during the winter. First, you’ll want to opt for a short that is a thicker material and wear it with a belt. Pair it with a cozy sweater, some chic Ankle boots. Last but not least, top the look off with a gorgeous coat . 


19 – Belt it up

Your favourite summer shorts work perfectly for fall. They make the outfit crisp, new, and extra stylish. Simply adding a belt to shorts and sweater is also another way to pull off shorts, its perfect for autumn and winter days. Don’t miss out on the cuteness, have a look!


18 – Smart Look for Office

Awaken your inner fashionista and take your style up another notch with a stunning Blazer. It is always smart to cover up the upper body with a blazer so as to keep yourself warm even in shorts. You can wear this outfit for a meeting at the office, a classy evening out, or any time when you want a sleek and structured look, you can’t go wrong with this look. For more amazing professional outfits, check out these 20 Ideal Spring Work Wear Outfits For Women for Elegant Look

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17 – Hot Casual Outfit with Shorts

Make a statement in these black buttoned shorts! They’re edgy, feminine, and ready for anything. Wear buttoned shorts to give yourself a more casual but hot look. This outfit will keep you warm, cosy and feeling weekend-ready. There is something so romantic and elegant about a winter white. All you need is a white crop top, leggings, and a pair of stylish black heels.

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16 – Brunch Look

Another great way to wear shorts in the winter season is simply adding a pair of sheer tights under them. This will create a flawless and sleek look. A ribbed knit off-white sweater is tucked in high-waisted  shorts completed with black Ankle boots. You can complete this look with an oversized blazer or a coat.


15 – Go All Black

Who doesn’t love an all black outfit ? This gorgeous is wearing a black lieutenant’s hat with a black sweater tucked in black leather shorts with a wide leather belt completed with sassy black tights and suede black ankle boots. A perfect all-in-black outfit idea for young women. We see a kind of Parisian chic outfit idea for Fall. When in Paris do as the Parisians do!

14 – Jacket and Scarves

Getting down and dirty in the Great Outdoors this weekend? Here is an outfit that will allow you to look cute without sacrificing functionality. This outfit will keep you warm, cosy and feeling weekend-ready. For winters, pair up denim shorts with leather jackets and scarf to keep you warm. Pair your denim shorts with cute leggings for that extra warmth and you’re good to go ! Add a finished feel to almost any outfit with a pair of Ankle boots.

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13 – Fancy Tights

Lots of fashionistas advise to wear black tights with black shorts, this combination can make your legs visually look longer. I also love to see women who use patterned tights, instead of classic black or sheer designs. Have a look at this outfit. Wear a black blazer worn with a grey sweater combined with shorts, polka dot tights, and classic black leather ankle-boots. Combine your shorts with fancy tights; this instantly uplifts the entire dress code.

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12 – Street Style

Check out this cool street style look consisting of a cool biker jacket, rock turtleneck top tucked in brown high-waisted ribbon shorts completed with black Shoes. Slay your favourite shades for extra style. It’s a classy and alluring look. 

11 – Velvet Shorts

Yes, velvet shorts look sassy and glamourous! Here is an inspo of a black leather jacket with a white pussy-bow blouse tucked in black velvet shorts completed with thigh high Leather boots.


10 – Bike Shorts

Yes, bike shorts can be used in the winter season. Keeping it casual yet fab is the way to do it on Sundays. Everyone has a denim jacket laying in their wardrobe. If you do, it’s time to take it out. Here we see an oversized denim jacket layered over a black sweater combined with black bike shorts and white sneakers. Top off the look with a body bag and your favourite shades 

9 – Leather Shorts

For winters another great tip is to opt for leather shorts than regular shorts as these are much warmer. That’s a perfect outfit for day walk on the town. We see a warm coat worn with cable-knit white sweater, black leather shorts, sexy tights and pointed ankle boots. Complete this look by adding a bag and scarf.

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Here we also see Miranda Kerr carrying her leather shorts in winters!

How to Wear Shrts in Winters


8 – Long Coats for the Win

Pair your shorts with long coats; these are much beneficial as they keep you warm almost till knees. My favourite combo so far. We see an oversized beige coat teamed with a white shirt tucked in black leather shorts. She is wearing thigh high heeled boots for that extra warmth. Update this look with mirrored rounded sunglasses

7 – Printed Shorts

Do you desire a comfortable but trendy look? Here’s the answer to your question. Just look at how resplendent yet comfortable this looks. This Short Outfit should be the ultimate choice. If you prefer funky fashion then wear printed shorts with plain tees or tops and combine with coats or jackets. How effortlessly chic does she look ?

6 – Scarves and Sweaters 

Scarves and sweaters are everyone’s favourite in winters. A sweater dress happens to be all the things: comfortable, fashionable, and practical. Plus, it’s a one-and-done outfit that can be amped up in many different ways.  So wear them with shorts, for foot wear women can wear long or short boots and complete the look. She styled her outfit by tucking just a portion of the sweater in for a deliberately unkempt look.

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5 – Shorts and Cardigan

Occasionally steer away from coats. Stay warm in a thick sweater combined with a fur vest instead. This would work well with a pair of shorts. You can also wear a pair of tights to crank up the warm factor of your ensemble. She is wearing a cardigan on top of a white top tucked in leathers shorts. She is wearing leopard print mules and a backpack.

4 – Denim and Sweater Look

If you want to keep it casual and cool, then go for denim! Denim is a cool way to underline your casual style and individuality. You are free to choose loose-fit denim shorts, cut-offs, mini, boyfriend shorts, etc. A white knit oversized turtleneck sweater is teamed with denim boyfriend shorts . Complete this look with white leather Ankle boots and a black leather crossbody bag. Hailey Bieber is killing this casual yet chic fall outfit.

3 – Holiday Outfit

If you’re looking for the happy medium between jeans and sweats these holidays, we suggest revolving your holiday outfit around a pair of Black shorts. If you’re looking for some extra holiday spirit — as well as a piece that will pop — you can always choose joyful, seasonal colours , such as green, blue, red or even white. These boots will complete your look 

2 – The Mighty Cape

Capes are an absolute favourite style statement and surprisingly they add loads of layers and go well with shorts too. You can add extra warmth by adding tick, soft socks, like over-the-knee ones or chunky mountain alike to team them with your favorite boots or booties. If you like this style then you’ll love these Cape Outfit Ideas – 25 Stylish Ways to Wear Cape Fashionably.

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1 – Woolen Shorts for Winters

The best way is to wear a lot of woolen and heavy textured tops with shorts to keep yourself all cozy in winters. An alternative to tights is leggings. All you need is to choose a pair of warm leggings and team them with your favorite shorts. 

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Frequently Asked Questions

Why do some people wear shorts during winter?

Shorts can be worn in the winter, even in locations with a cool climate, as it is being worn as a fashion statement. Another reason can also be the person’s body temperature. They may wear shorts in winter because they have a different threshold of cold than you do.

Do girls like to wear shorts in the winter?

Winters shouldn’t be a reason for you to ditch shorts. You can style it in multiple ways and wear what you love.

  1. Stockings – The good old stockings beneath a pair of shorts are guaranteed to keep you warm and make your look dapper.

2. Knee High Boots – Not only are they a winter essential but pair up excellently with shorts.

3. Long Over Coat – Another item from your winter must-haves that compliment dresses, shorts, and skirts beautifully in the intense cold.


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    • Olivia Davis

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