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What They Never Told You About Winter Shorts Outfits

When winter rolls around, shorts might not be the first thing you think to pull out of your closet. But let me tell you—winter shorts outfits can be a fabulous, unexpected addition to your cold-weather wardrobe.

Quote of the day: “Surround yourself with only people who are going to lift you higher.” Oprah Winfrey

What they never told you is that with the right layers and styling tips, you can make this trend work for nearly any occasion, all while staying warm and chic.
Plus, they add the element of FUN to your look.

If you’re worried about staying warm, many of these winter shorts outfits are cozier than jeans. As well as they add to the variety of your everyday looks.

Insider tip: Honestly, with these tips and ideas, I have been known to wear shorts more in the winter than I do in the summer. I feel covered, modest, and comfortable in my winter shorts outfits.
Plus, it’s the opposite of being frumpy.

Why Shorts in Winter?

Shorts in winter might sound counterintuitive, but they offer a unique way to break out of the typical cold-weather rut of jeans and leggings. Pairing your favorite shorts with cozy winter staples, like fleece-lined tights, tall boots, and chunky knits, creates an ensemble that’s equal parts fun and functional.

In addition, it’s a great way to extend the wearability of your summer and fall pieces.

Making our clothing work for more seasons, more occasions, and more, in general, is good for our brains as well as our wallets.

Insider tip: Did you know creating “new” outfits is a brain activity? You are producing new brain pathways which is just as effective as learning a new language. So go play in your closet and make yourself put together items you haven’t paired in the past.

The Key to Winter Shorts Outfits: Layers

The trick to making winter shorts outfits work is all about the layers. You’re not just throwing on your summer shorts and braving the cold—you’re building an outfit that’s warm, stylish, and practical. Here are some essential elements to consider:

Insider tip: If you don’t have a pair of tights to go with your outfit, don’t forget to check your workout leggings. They can be the perfect layering options as I’ve showcased before.

  • Tall Boots: Knee-high or over-the-knee boots are the perfect footwear choice for winter shorts outfits. Not only do they add extra warmth, but they are the perfect way to showcase the beauty of them. If you wear them under long dresses or pants, you don’t get to appreciate how they look in their entirety.
  • Chunky Sweaters and Coats: A cozy sweater or a tailored coat balances the proportions of shorts while keeping your upper half snug. Think oversized knits, turtlenecks, or even a chic blazer.
  • Accessories: Don’t forget the finishing touches! Just because it’s cold doesn’t mean you should forget fun earrings or heck, even a tiara. Obviously, scarves and beanies can be the perfect pairing.

Insider tip: For those of you who live where it doesn’t get as cold, think about thinner hosiery or no tights. You’ll still feel covered if you are wearing tall boots.

As much as I love my site, Jodie’s Touch of Style, I really enjoy putting together my daily emails. I consider my emails an extension of my blog that is chocked full of positive inspiration that one friend calls a “Variety Show.”
I include articles, videos, and posts that strike my fancy and since I have no siblings to share with, I share with you.

Styling Inspiration: Winter Shorts Outfits for Every Occasion

Now that you’ve got the basics, let’s dive into some outfit ideas to inspire your winter wardrobe.

1. Casual Errands and Coffee Dates

For a relaxed yet stylish look, pair denim shorts with fleece-lined tights, a chunky knit sweater, and ankle boots.

2. Date Night Glam

For a romantic evening out, choose leather or faux leather shorts for a touch of edge. Pair them with sheer patterned tights, a silky blouse, and heeled boots. Add a statement coat and tons of fun accessories.

3. Outdoor Adventures

Are you heading to a winter market or ice skating rink? Opt for wool or corduroy shorts for extra warmth. Layer with thick tights, a thermal turtleneck, and a quilted vest. Finish the look with insulated snow boots, a pom-pom beanie, and mittens. This outfit is functional and adorable for any outdoor activity.

4. Trendy and Edgy

For a street-style-inspired look, try Bermuda shorts layered over colorful tights. Add a graphic sweatshirt and an oversized puffer coat. Combat boots or chunky sneakers keep the outfit modern and edgy.

Shorts for Every Style

One of the best things about winter shorts outfits is that they’re incredibly versatile. Whether your style leans classic, boho, edgy, or preppy, there’s a way to make this trend work for you.

  • Classic: Tailored shorts in wool or tweed
  • Boho: Denim or corduroy shorts
  • Edgy: Leather shorts
  • Preppy: Plaid shorts

Insider tip: Remember, you can create shorts at the length you want by shortening a pair of jeans or pants.

I’m not saying you can’t wear your summer shorts for this idea, but there are many materials that seem perfect for winter. In fact, I can’t wear my faux leather shorts in the summer because they are too warm.

Mixing and Matching Textures

Winter fashion is all about textures, and winter shorts outfits are no exception. Experiment with combinations like:

  • Wool shorts + chunky knit sweater
  • Faux leather shorts + silk blouse
  • Corduroy shorts + fleece-lined tights
  • Denim shorts + velvet blazer

Mixing textures adds depth and interest to your outfit, making it feel intentional and stylish.

Practical Tips for Staying Warm

If you’re worried about staying warm, here are a few extra tips to keep in mind:

  • Layer thermals under your tights for added insulation or wear a pair of hosiery under your tights.
  • Choose shorts made from heavier fabrics like wool, corduroy, or leather.
  • Opt for sheepskin insoles to keep your feet toasty.

Why You Should Try Winter Shorts Outfits

If you’ve never tried wearing shorts in winter, now is the perfect time to experiment. This idea is not only fun but also a great way to get more use out of your wardrobe. By mixing and matching pieces you already own, you can create unique looks that stand out from the sea of jeans and leggings. Plus, there’s something undeniably confident about pulling off a pair of shorts when the temperatures drop.

Facts: Jodie’s Touch of Style is supported by my readers. I partner with affiliate platforms where commission may be earned based on your purchases. If you decide to buy anything I’ve promoted, I appreciate you using my link. These links help bloggers like me to fund the content that we provide, plus it tells companies that blogging marketing works. Thank you for your ongoing support.

Final Thoughts

Winter shorts outfits are a playful, unexpected way to shake up your cold-weather style. With the right layers, textures, and accessories, you can create looks that are warm, chic, and totally you.

So don’t be afraid to step outside your comfort zone and give this a try. And remember, fashion is all about having fun—even when it’s freezing outside!

Winter Shorts Outfits

Photo credit: Rob Filogomo

Thank You

I hope I thank you enough because your support allows me to continue this journey which I LOVE!!!
Supporting a blog can be easy and free. Just visiting my pages, clicking my links (especially for Small Businesses and sponsored posts), and sharing the things you like on your social media make a huge difference. Spreading the word is how I can reach more wonderful people like you!  
Or feel free to “buy me a coffee” which is a monetary way to tell me that you enjoy reading my blog.

Layering Lace Under Bulky Sweater

Welcome to Jodie’s Touch of Style. I’m here to prove that it’s never too late to look great. Clothing and style are meant to showcase your inner personality. So let’s have fun and try new things.

The post What They Never Told You About Winter Shorts Outfits appeared first on Jodie’s Touch of Style.

Jodie's Touch of Style showcases how it's never too late to look great including other older women and myself talking about fashion, beauty, and lifestyle issues.

As a retired dentist, Jodie takes her love of clothing and shopping and has come to find her superpowers in styling the same item in many ways. She is also a huge advocate for embracing our age and bodies. Getting old is a wonderful thing and learning to love ourselves while it happens is very freeing.

Looking great can happen no matter what age, shape or budget, as we show on Jodie's Touch of Style.

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