Stay Warm and Stylish: How To Wear Shorts in Winter and Fall

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Just because it’s cold outside doesn’t mean you have to stop rocking your favorite pairs of shorts. By following the top styling and layering tips, you can wear what you love year-round.

Our cold-weather outfit ideas will help you choose the best shorts, jackets, and boots so you can get the most out of your wardrobe. Read our guide and learn how to wear shorts in the winter or anytime it’s chilly.

How to choose the perfect winter shorts

Picking the right type of shorts makes a major difference in cold weather. While fabrics like linen and rayon are lightweight and comfortable, they don’t offer enough protection from chilly air and wind.

The best winter outfit shorts are made of durable materials like leather, suede, and wool. These fabrics are thicker and warmer. As a bonus, they also pair well with other winter clothing staples, like sweaters and aviator jackets.

Another consideration when picking the perfect shorts for winter is the color palette. In colder months, people tend to reach for dark, earthy colors like navy and plum. But if you prefer lighter colors, options like baby pink and light blue create a winter wonderland aesthetic.

How to wear shorts in cold weather: 8 outfit ideas and styling tips

Here’s how to wear shorts in the cold and flaunt your personal style in any season.

‍Pro tip: All these ideas double as top-tier winter skirt outfits!

1. Cozy charm

We’ve found your new cold-weather go-to: A chunky turtleneck, suede shorts, and ankle boots. A simple pair of socks will be enough for early fall days, but we recommend tights or leggings as the temperature drops.

This combo has a classic allure, perfect for a day at the orchard or a trip to the coffee shop for a seasonal latte. Although this outfit works with any color palette, it’s one of our favorite winter white outfits. Ivory knits and white suede shorts are perfect for a snowy backdrop.

2. Polished and sleek

If you’re interested in a more sophisticated look, try a cashmere sweater, trouser shorts, and a wool trench coat. To protect your legs against the cold, reach for a jacket with a long hemline.

Take your outfit to the next level with Chelsea boots. We’ll admit it—we built this outfit around these shoes. They’re one of the best winter boots, balancing practical features with a refined aesthetic.

‍Pro tip: You can also pair a trench coat and Chelseas with a warm winter dress.

3. Edgy contrast

Add an edge to your oversized striped sweater with black leather shorts, and French-tuck the top for a relaxed style. For extra attitude (and to cover your knees in the wind), pair this with thigh-high boots. 

The bulky sweater creates a contrasting silhouette against the sleek shorts and shoes. To continue the contrast in your color palette, pick colorful stripes—like pink and purple—that stand out against the black leather.

4. Captivating cardigan

A comfy cardigan with oversized buttons pairs perfectly with checked wool shorts. Finish this look with smooth knee-high boots, tights, and a knit beanie. This polished outfit is ideal for lunch with friends or a laid-back coffee date. 

We love matching the cardigan and hat in pale cream and choosing a tawny gray for the shorts. But the sky’s the limit—this getup would be stunning in maroon or eggplant, too.

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5. Sporty and snug

Need something heavy duty? Wear a sweatshirt, your favorite winter jacket (we love a puffer trench coat), fleece shorts, and leggings. Don’t forget to keep your feet warm and dry with toasty snow boots.

This is our top suggestion for wearing shorts in snow, high winds, and winter storms. While many people would opt for pants in these situations, a shorts-leggings combo offers lightweight flexibility that keeps you from feeling bogged down.

6. Polar power

The right outfit helps you stay warm and strong during cold activities, whether you’re into winter sports or brisk morning jogs. Layer workout shorts over thermal fleece-lined leggings to stay flexible and warm. 

For the top, choose a moisture-wicking long-sleeve or sweatshirt. Add a knit hat and a puffy vest to conquer your next icy workout.

7. Nineties rebel

The 1990s are making a big comeback, and we couldn’t be happier about it. Jump on this trend by throwing on a white long-sleeve shirt, leather jacket, and denim shorts. And for a splash of color, add a bold red scarf.

This outfit works well with chunky white sneakers or high tops, but if the weather doesn’t allow, you can amp up the warmth with a heavy pair of Doc Martens.

8. Preppy perfection

Embrace your preppy, elegant side with high-waisted shorts, a cable-knit sweater, and riding boots. Hold onto your warmth and stay snug with an oversized wool blazer.

This academic aesthetic is a stylish travel look, perfect for exploring city streets and sipping local wines.

Discover winter shorts and layering essentials on ThredUp

ThredUp is your best resource for warm winter shorts and layering essentials, from jackets to sleek boots. Build the perfect outfit by exploring our massive inventory—we receive 50,000 new items daily.

Our intuitive search tools let you narrow your options and find your next closet staple in seconds. Drag and drop your inspo pics into our Image Search, and we’ll suggest an item from our collection for every visible piece.

And if you don’t know exactly what you’re shopping for, get inspired with Style Chat. Describe clothing pieces, seasons, or vibes, and we’ll generate an outfit on a model. Adjust the idea with prompts like “Less colors” and “More formal,” or type your own, like “Add a knit beanie.”

When you’re done, browse suggestions from our selection in the right column and thrift your new outfit in seconds.

Shop smarter with ThredUp.

FAQs

What do you wear under shorts when it’s cold? 

The best options for cold-weather layering include fleece-lined leggings and thick tights. Our favorite trick is wearing multiple pairs for the ultimate warmth. 

But layering doesn’t stop at pants—your footwear is just as important. Reach for knee-high socks and boots for added protection from the cold weather, or choose snow boots to get a little extra traction. 

Can you hike in shorts in winter? 

Yes, you can definitely hike in shorts in winter! Start by checking your forecast to see what the conditions will be. If it’s clear and chilly, go for the “sporty and snug” combo above. Stretchy leggings and puffy vests will keep you warm while letting you stay flexible. If it’s raining or snowing, opt for weather-proof fabrics that repel moisture.

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