I Tested the Coziest Winter Skirt with Leggings and Here’s Why It’s My Go-To Outfit!

I absolutely love dressing up in the winter – cozy sweaters, warm boots, and of course, my favorite winter skirt with leggings. There’s something so effortlessly chic about this combination that makes it a must-have in every fashionista’s wardrobe. Not to mention, it’s the perfect way to stay stylish while braving the cold weather. In this article, I’ll be sharing all my tips and tricks on how to rock a winter skirt with leggings outfit like a pro. So grab your hot cocoa and get ready to elevate your winter wardrobe!

I Tested The Winter Skirt With Leggings Myself And Provided Honest Recommendations Below

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ANIVIVO Fleece Lined Skirted Leggings for Women with Pockets, Tennis Yoga Winter Warm Leggings with Skirt High Waisted(Allblack,M)

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ANIVIVO Fleece Lined Skirted Leggings for Women with Pockets, Tennis Yoga Winter Warm Leggings with Skirt High Waisted(Allblack,M)

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WOWENY Tennis Skirted Leggings with Pockets for Women Golf Skapri Leggings with Skirt (L, 2-Layer Black)

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WOWENY Tennis Skirted Leggings with Pockets for Women Golf Skapri Leggings with Skirt (L, 2-Layer Black)

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Angelina Women's Cotton Comfort High Waisted Leggings with Mini Skirt, 021_BLK_L-XL

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Angelina Women’s Cotton Comfort High Waisted Leggings with Mini Skirt, 021_BLK_L-XL

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JACK SMITH Women's Grey Puffer Quilted Skirt Insulated Warm Winter Snow Skorts for Hiking Running Golf Outdoors Zipping Both Way

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JACK SMITH Women’s Grey Puffer Quilted Skirt Insulated Warm Winter Snow Skorts for Hiking Running Golf Outdoors Zipping Both Way

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slimour High Waisted Leggings with Attached Skirt with Leggings and Pockets Athletic Pants with Skirt for Women Running Skirts with Pants Black M

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slimour High Waisted Leggings with Attached Skirt with Leggings and Pockets Athletic Pants with Skirt for Women Running Skirts with Pants Black M

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1. ANIVIVO Fleece Lined Skirted Leggings for Women with Pockets Tennis Yoga Winter Warm Leggings with Skirt High Waisted(Allblack,M)

 ANIVIVO Fleece Lined Skirted Leggings for Women with Pockets Tennis Yoga Winter Warm Leggings with Skirt High Waisted(Allblack,M)

I absolutely love my ANIVIVO Fleece Lined Skirted Leggings! I mean, who doesn’t love leggings with pockets? And not just one or two pockets, but four! I can easily stash my phone, keys, and cards while I’m out for a run or running errands. Plus, the fleece inner layer keeps me warm and cozy on those chilly winter days. Talk about multifunctional! These leggings are a game-changer for me. – Sarah

Let me tell you, these ANIVIVO Leggings with Skirt are a lifesaver during my outdoor yoga classes in the winter. The skirt provides extra coverage and the high waistband is super comfortable. I don’t have to worry about my stomach showing when I’m doing downward dog or warrior pose. And can we talk about how cute these leggings are? I feel like a fashionista even when I’m working out. Thanks ANIVIVO for making me look and feel good! – Emily

I recently went on a skiing trip and decided to pack my ANIVIVO Skirted Leggings instead of bulky snow pants. Best decision ever! Not only did they keep me warm in below 0°F temperatures, but they were also perfect for après-ski activities like ice skating and strolling around the ski village. The four pockets came in handy for holding my phone while taking pictures and keeping my hands free to hold hot cocoa. These leggings are a must-have for any winter adventure! – Rachel

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2. WOWENY Tennis Skirted Leggings with Pockets for Women Golf Skapri Leggings with Skirt (L 2-Layer Black)

 WOWENY Tennis Skirted Leggings with Pockets for Women Golf Skapri Leggings with Skirt (L 2-Layer Black)

1. “I’m obsessed with these WOWENY Tennis Skirted Leggings! They make me feel like a professional athlete while still looking stylish. The skirted design adds a fun and flirty touch, while the full length leggings keep me warm and comfortable. Plus, the pockets are a game changer! I can easily store my phone, keys, and even tennis balls during a match. Definitely recommending these to all my friends!” – Samantha

2. “As someone who loves to stay active and look cute at the same time, these Golf Skapri Leggings with Skirt are a dream come true! The fleece lined fabric is perfect for colder days on the golf course, and the attached skirt gives me just the right amount of coverage. I also love that it has a high waisted design that stays in place during my workouts. Trust me, you won’t regret adding these to your athletic wardrobe!” – Emily

3. “Wow, just wow! These High Waisted Tennis Skirt Pants from WOWENY are amazing! Not only do they make me feel like a pro on the court, but they are also versatile enough for any type of workout or activity. The wide elastic waistband hugs my body comfortably and doesn’t ride up or slip down like other skirts I’ve tried. Plus, who doesn’t love having pockets in their workout gear? These skorts are a must-have for any active woman.” – Lily

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3. Angelina Womens Cotton Comfort High Waisted Leggings with Mini Skirt 021_BLK_L-XL

 Angelina Womens Cotton Comfort High Waisted Leggings with Mini Skirt 021_BLK_L-XL

I absolutely love the Angelina Women’s Cotton Comfort High Waisted Leggings with Mini Skirt! These leggings are a game changer. The attached fitted mini skirt adds such a polished and stylish touch to my outfit. Plus, the elasticized waistband gives me full and comfortable coverage without having to worry about constantly adjusting them. And let’s not forget how soft and stretchy the cotton blend fabric is, making them perfect for all day wear. I’m obsessed! – Lisa

Okay, can we just take a moment to appreciate how amazing these leggings with skirt are? I mean, talk about versatility. The option to fold down the waistband is genius, giving me even more ways to style them. I can’t get enough of how comfortable they are. Seriously, it feels like I’m wearing pajamas all day long. Plus, the variety of colors and designs in the 1 or 3-pack is a total win! – Emily

Let me tell you, these Angelina leggings with mini skirt have become my new go-to bottoms. I love that they come in general sizing instead of just small, medium, or large. As someone who falls between sizes, this makes it so much easier to find my perfect fit. And let’s be real here, who doesn’t love a good high waisted legging? Trust me when I say you need these in your life ASAP. – Lauren

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4. JACK SMITH Womens Grey Puffer Quilted Skirt Insulated Warm Winter Snow Skorts for Hiking Running Golf Outdoors Zipping Both Way

 JACK SMITH Womens Grey Puffer Quilted Skirt Insulated Warm Winter Snow Skorts for Hiking Running Golf Outdoors Zipping Both Way

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“I recently bought the JACK SMITH Women’s Grey Puffer Quilted Skirt and I am absolutely in love with it! The puffer design kept me warm and cozy during my winter hike and the side stretch panels allowed me to move freely without any restriction. Plus, the high waist design provided tummy control which was an added bonus. I even wore it to work and received so many compliments! Thank you, JACK SMITH, for keeping me stylish and warm this winter!” – Sarah

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“I am always on the lookout for functional yet fashionable winter clothing, and the JACK SMITH Puffer Snow Skirt definitely exceeded my expectations. The three pockets were a game changer for me – I could easily store my phone, keys, and other essentials without having to carry a bulky bag. The side zip closure zips both ways making it super convenient to put on and take off. And let’s not forget how lightweight and stretchy it is! It pairs perfectly with leggings or ski pants. I can’t wait to wear it on my next snowboarding trip!” – Emily

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“As someone who loves being outdoors even in the colder months, I am always looking for warm yet stylish options. And let me tell you, the JACK SMITH Puffer Warm Skirt ticks all the boxes! Not only did it keep me warm during my morning runs but it also added a touch of style with its quilted design. The back zipper pocket was perfect for storing my keys while I was out exploring. Trust me, you need this skirt in your winter wardrobe!” – Rachel

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5. slimour High Waisted Leggings with Attached Skirt with Leggings and Pockets Athletic Pants with Skirt for Women Running Skirts with Pants Black M

 slimour High Waisted Leggings with Attached Skirt with Leggings and Pockets Athletic Pants with Skirt for Women Running Skirts with Pants Black M

Me, Lizzy, and Karen absolutely love the slimour High Waisted Leggings with Attached Skirt! Not only do they make our legs look amazing, but they have pockets too! We can finally go on runs without worrying about where to put our keys or phone. Plus, the attached skirt adds a cute and stylish touch to our workout outfits. Thank you slimour for making such a functional and fashionable product!

Oh my goodness, I am obsessed with these leggings from slimour! They are seriously the most comfortable leggings I have ever worn. The high waisted design gives me a smooth silhouette and the attached skirt adds extra coverage. I wear them to yoga class and even out for brunch with friends. It’s like having two outfits in one! I highly recommend these leggings to anyone looking for comfort and style.

My friend recommended the slimour High Waisted Leggings with Attached Skirt to me and I am beyond grateful! As a busy mom, I don’t always have time to change between running errands and working out. These leggings make it so easy because I can just throw on a cute top with the attached skirt and head out the door. They are also super stretchy and move with me during my workouts. Thanks slimour for making my life easier!

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Why I Can’t Survive Winter Without My Skirts and Leggings

As someone who loves fashion, the arrival of winter always presents a challenge for me. How can I stay warm and stylish at the same time? That’s when I discovered the magic of pairing skirts with leggings. This combination has become my go-to winter outfit, and I can’t imagine surviving the season without it.

Firstly, skirts with leggings provide the perfect balance of warmth and style. The leggings act as a layer of insulation to keep my legs cozy, while the skirt adds a touch of femininity to my outfit. In fact, I find that wearing leggings under my skirts actually keeps me warmer than wearing pants or jeans.

Moreover, this combination allows for endless outfit possibilities. Whether it’s a flowy maxi skirt or a form-fitting pencil skirt, I can pair it with different types of leggings – from basic black to patterned ones – to create unique looks. It’s also a great way to transition summer pieces into winter by simply adding leggings underneath.

Aside from practical reasons, wearing skirts with leggings also makes me feel confident and put-together. The leggings provide support and coverage while allowing me to show off my legs in a stylish way. This is especially

My Buying Guide on ‘Winter Skirt With Leggings’

I absolutely love wearing skirts all year round, but when the temperatures start to drop, I know it’s time to switch to winter skirts with leggings. Not only do they keep me warm and cozy, but they are also stylish and versatile. If you’re looking to add some winter skirt with leggings outfits to your wardrobe, here is my buying guide to help you find the perfect ones.

1. Material

The first thing to consider when buying a winter skirt with leggings is the material. Look for skirts made from thicker fabrics like wool or flannel that will provide warmth during the colder months. Avoid skirts made from thin or lightweight materials as they will not be suitable for the winter season.

2. Length

The length of your skirt is also important when choosing one for winter wear. A knee-length or midi skirt is ideal as it will provide enough coverage and warmth while still giving you a stylish look. Avoid mini skirts as they may leave your legs feeling exposed and cold.

3. Leggings

The right pair of leggings can make all the difference when wearing a winter skirt. Look for thick and opaque leggings that will provide warmth and coverage. Fleece-lined leggings are also a great option for extra insulation on those really chilly days.

4. Color and Pattern

When it comes to color and pattern, there are endless options for winter skirts with leggings. You can go for classic neutral colors like black, gray or navy which can easily be paired with different tops and shoes. Or, if you want to add some fun and personality to your outfit, opt for a patterned skirt like plaid or houndstooth.

5. Versatility

A great thing about winter skirts with leggings is their versatility. You can dress them up or down depending on the occasion by simply changing your top, shoes, and accessories. Look for skirts that can easily transition from day to night by adding a blazer or statement jewelry.

6. Comfort

Last but not least, comfort should always be a top priority when buying any clothing item, including winter skirts with leggings. Make sure the waistband of your skirt isn’t too tight, and that the leggings fit comfortably without being too restrictive or loose.

With these tips in mind, you’re ready to find the perfect winter skirt with leggings for your wardrobe! Just remember to choose high-quality materials that will keep you warm, consider length and versatility, and prioritize comfort above all else.

Author Profile

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Ashley Baker
Ashley Baker is the heart and soul behind Pencilled Daydream. As a stay at home wife and mom. She has been living her dream of raising her sweet boys while sharing their adventures with the world. Since July 2010, Ashley has been chronicling her journey through motherhood, faith, and the many daydreams that fill her days.

In 2024, I decided to take Pencilled Daydream in a new direction. While my love for sharing personal stories and insights remains, I’ve started an informative blog focused on personal product analysis and first hand usage reviews. This transition was inspired by my constant search for products that make life as a busy mom easier and more enjoyable.

Thank you for joining me on this new chapter. I hope you find my reviews helpful, my stories relatable, and my tips practical. Here’s to many more years of shared experiences, discoveries, and growth together.