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The age-old dilemma of “I want to wear a skirt…but it’s cold out!” is something many of us have experienced. If you’re a massive skirt enthusiast you may be guilty of blindly choosing to wear a skirt only to suffer the frigid consequences later.
Like dresses, skirts are an extremely versatile asset in your travel wardrobe especially if you’re going on a trip with different weather. Take a look at these skirt outfits to learn how to wear them in cold weather!
Skirt Outfits for Cold Weather
Table Of Contents
Fashion is all about expressing yourself and having fun, but it’s not much fun when you feel like you’re on the verge of hypothermia! With experimentation, however, I’ve slowly come to learn that skirts can be a possibility in colder temperatures, as long as there’s a strategic approach.
Start by reading these general tips on packing for winter travel:
- Capsule Wardrobe for Winter
- How to Pack for Cold Weather
- How to Stay Warm in Cold Weather (without the bulk)
- The Best Travel Shoes for Winter
Nowadays, I’m all for wearing skirts year-round. I can confidently say that they are–more often than not–a great idea to include in your capsule wardrobe! Skirts are fun, feminine, and fabulous, and shouldn’t have to collect dust in our wardrobes simply because it’s cold outside!
With a keen eye towards fabric selection, strategic layering, and overall styling, one can make a skirt withstand frigid temperatures and keep it as a wardrobe staple all year long.
Here’s a season-to-season guide on skirt outfits for travel. Learn how to rock these beloved garments even when the cold strikes and see some suggested skirts you could add to your wardrobe!
Jacket | Longsleeve | Scarf | Skirt | Lipstick | Boots | Bag | Tights
Autumn is all about fabrics! We’re loving suede, knits, and leather. And luckily for us, these also keep us warm and stylish (and don’t wrinkle inside your packing cube easily, too)! Corduroy and leather, in particular, are effective at heat capture, so plan skirt outfits in those materials.
A leather jacket, corduroy skirt, and a cozy rib knit sweater come together to make a lovely fall outfit. Throw in some gray cable knit tights, a scarf, a pair of boots, and a toasty cinnamon latte to fully channel all those quintessential fall vibes.
Here are more fall fashion ideas!
Check out these other top selections for best fall skirts:
Shop Sizes S-XXL: Amazon
Fahsyee Faux Leather Skirt
This Fahsyee bodycon faux leather skirt will give you all the sass you need to walk with confidence down the street while the orange and red leaves dance around you. Pair it with a knee-high boot for cooler days or a pair of ballet flats to add some class and chic.
This cute number has a smooth lining and breathable fabric and is said to be comfortable. It also comes in sizes S-XXL and in a variety of lengths too, if you prefer something shorter.
One user agrees with its versatility and says, “As soon as I put it on, it fit like a glove. This is going to be a staple for going out. Can dress up or down easily with a t-shirt and sneakers or a cute blouse and heels. Highly recommend this skirt!”
Shop Sizes Plus 12-34: Amazon | Walmart
Woman Within Corduroy Skirt (Plus Size)
This Woman Within A-line corduroy skirt accentuates the waistline and elongates your figure so that you look fab even while devouring a warm croissant in Paris. It’s offered in various muted colors that are ideal to add to a travel capsule wardrobe.
A wearer notes, “Elastic in the back puts it on the more roomy side in the waist fitting. If you desire a more form-fitting look you are able to size down. Very flared toward the bottom. Long enough to cover the top of your knee boots.”
Since the material is a bit heavier, it’ll keep you warm during fall and even winter. Throw on a classy sweater and some knee high boots and you’ll stay warm (and cute) all night long! Grab this in sizes 12-34 Plus.
Shop Sizes XS-XL: Amazon | Fishers Finery
Fishers Finery Pencil Skirt
For eco-friendly seekers, this Fishers Finery stretchy pencil skirt is made with ethically sourced cotton, bamboo viscose, and polyester. The fabric isn’t see through either and more substantial, so that makes it ultra comfy and ensures no wrinkles throughout the day!
Offered in neutral colors you can quite literally wear this with anything from a snazzy pair of sneakers and an off-the-shoulder sweater or ankle booties and a long sleeve blouse.
For a functional skirt, this one hits the nail on the head. A reviewer agrees, “I was looking for an easy versatile travel skirt for a cruise. This far exceeded my expectations! Amazingly soft, kept its shape, and easy to care for. I highly recommend this purchase!” Available in sizes XS-XL.
Jacket | Scarf | Sweater | Tights | Belt | Skirt | Backpack | Boots
The thought of donning a skirt in the middle of winter may seem crazy at first, but if you choose fabric wisely and layer appropriately, you’ll find that it may not be so bad after all!
A flared, midi winter skirt with merino tights underneath is sure to do the trick. Since these skirts are so voluminous, keep the upper half of your look fitted and balanced with a sweater tucked in and a few mid and base layers if necessary.
I would not advise pairing a bulky coat with this sort of skirt as you may look drowned out by all the fabric. Instead, opt for cropped outerwear such as a short moto leather jacket. Finish off the look with ankle boots, and a cream cashmere scarf for a lovely winter feel.
These are the best waterproof boots according to our readers!
Check out these other top selections for best winter skirts:
Shop J.Crew: Classic 00-24 | Petite 00-12
J.Crew No. 2 Pencil® Skirt in Italian Stretch Wool
This classy midi-length J.Crew wool skirt comes in three staple colors and can help you stay warm and stand out from the crowd around the holidays. Picture yourself with some sheer tights, an elegant sweater, and dangly earrings, all while sipping an apple cider cocktail.
One fan of this piece shares their experience, “It fits well, looks professional, has a bit of stretch, and is a great length. I will be buying this in more colors!” Available in sizes 00-24.
Shop Sizes XXS-XL: Macy’s
DKNY Sweater Pencil Skirt
Slide on this DKNY midi sweater skirt and harness your inner goddess! Pull the look together with a merino wool sweater and blazer or tuck in a chic turtleneck.
You can’t go wrong with a simple, yet classic fitted sweater skirt that elongates your figure, pairs easily with many outfits, and you can wear it from fall into spring.
A review says, “The skirt was everything and more. It fit perfectly following the sizing guide. It’s a nice weight and non-restrictive. I know I can take this piece from day to a night out on the town.”
Shop Sizes XS-XL: Amazon | Moosejaw | Smartwool | REI
Smartwool Women’s Smartloft Pull On Quilted Skirt
Stay cozy, confident, and active on your next holiday adventure with this Smartwool merino wool skirt. The waist sits at or below your belly button, the patterned design brings an extra pizazz, and there’s a side pocket for storing small valuables!
Many reviewers mentioned that these are “perfect over leggings for chilly days,” and this user heaps more accolades, “This marvelous mini is such a cozy skirt for cool weather. I absolutely love the fit and details. Soft fabric. Sweater material on the sides. Stretch. Great fit.”
In fact, you may want to pair them with fleece-lined leggings or add thermals beneath your regular leggings to bring the warmth up a notch.
Jacket | Skirt | Longsleeve | Bag | Boots | Earrings | Tights
As cliché as it may seem, floral skirts are perfect for springtime. A turtleneck sweater and a floral skirt make great partners in crime for a cute spring look. Fleece tights help keep chilly breezes at bay.
For extra warmth, layer a thermal top underneath the sweater. Make sure you throw waterproof boots and a jacket in there too – spring can be notorious for unpredictable weather!
Here are more spring fashion trends this season!
Check out these other top selections for best spring skirts:
Shop Boden: Sizes Regular 2-22 | Petite 2-12
Boden Straight Denim Midi Skirt
Since the 1970’s denim skirts have been a go-to in mainstream fashion and for good reason. Denim is like tabasco sauce—it goes with everything. And, the best part is it doesn’t require washing much so while you’re on the road you can wear it multiple times.
Riffing off classic five-pocket styles, this Boden denim skirt does what jeans can’t: it buttons all the way to the hem with a straight, structured fit.
Shop Sizes 0-22: Amazon
RipSkirt Hawaii New Length 3 Quick Wrap Cover-up
This brand is known for making water-resistant clothing that can go from pool to sidewalk cafe, and TFG readers adore them for travel!
And this gorgeous floral number screams springtime! Grab yourself a RipSkirt available in multiple different vibrant patterns to mark this time of year.
To wear it, use the velcro waistband to customize the size and feel light and airy.
When it comes to spring, wear this during the day with tights, a denim or rain jacket, and a light sweater beneath, or dress it up in the evening with waterproof ankle booties and statement earrings just like this reviewer says, “Perfect for day or evening. Sporty or dressed up. Flattering on any figure. Hangs beautifully. It packs compactly and never wrinkles.”
And bonus, this skirt can also take you into summer, which is wearable at the beach or by the pool! Available in sizes 0-22!
The RipSkirt Hawaii is adored by TFG readers, find out why in this review!
Shop Sizes XS-XL: Nordstrom
Loveappella Roll Top Maxi Skirt
With an adjustable roll top, added stretch, and flowy silhouette you’ll feel like living in this Loveappella flowy maxi skirt! Throw it on with a tee and cardigan and some ankle boots (don’t forget tights underneath) during the day and style it up with a dressy blouse and long boots at night.
One happy reviewer showers compliments, “Lovely fit and flow. Nice fabric, not heavy but not flimsy either!” Available in sizes XS-XL and a number of gorgeous neutrals that would fit with any capsule wardrobe.
And if you adore Loveappella as our readers do; you might be keen to pick up the Loveappella Flowy Maxi Dress for warmer weather, which is THE most popular maxi for the summer, as seen in this post!
Product Comparison Chart
|BRAND | MODEL||FEATURES | REVIEWS||RATING | PRICE|
|Best Fall Skirts|
|Fahsyee Faux Leather Skirt||“As soon as I put it on, it fit like a glove. This is going to be a staple for going out. Can dress up or down easily with a t-shirt and sneakers or a cute blouse and heels. Highly recommend this skirt!”||Check Price|
|Woman Within Corduroy Skirt (Plus Size)||“Elastic in the back puts it on the more roomy side in the waist fitting. If you desire a more form fitting look you are able to size down. Very flared toward the bottom. Long enough to cover the top of your knee boots.”||Check Price|
|Fishers Finery Pencil Skirt||“I was looking for an easy versatile travel skirt for a cruise. This far exceeded my expectations! Amazingly soft, kept its shape, and easy to care for. I highly recommend this purchase!||Check Price|
|Best Winter Skirts|
|J.Crew No. 2 Pencil® Skirt in Italian Stretch Wool||“It fits well, looks professional, has a bit of stretch, and is a great length. I will be buying this in more colors!”||Check Price|
|DKNY Sweater Pencil Skirt||“The skirt was everything and more. It fit perfectly following the sizing guide. It’s a nice weight and non-restrictive. I know I can take this piece from day to a night out on the town.”||Check Price|
|Smartwool Women’s Smartloft Pull On Quilted Skirt||“This marvelous mini is such a cozy skirt for cool weather. I absolutely love the fit and details. Soft fabric. Sweater material on the sides. Stretch. Great fit.”||Check Price|
|Best Spring Skirts|
|Boden Straight Denim Midi Skirt||Denim is like tabasco sauce—it goes with everything. And, the best part is it doesn’t require washing much so while you’re on the road you can wear it multiple times.||Check Price|
|RipSkirt Hawaii New Length 3 Quick Wrap Cover-up||“Perfect for day or evening. Sporty or dressed up. Flattering on any figure. Hangs beautifully. It packs compactly and never wrinkles.”||Check Price|
|Loveappella Roll Top Maxi Skirt||“Lovely fit and flow. Nice fabric, not heavy but not flimsy either!”||Check Price|
What are your favorite skirt outfits for cold weather? Share your thoughts below!
For more ideas on what to wear in cold weather, please read:
- How to Pack for Cold Weather Like a Boss
- 10 Best Thermal Underwear for Women
- How to Stay Warm in Cold Weather and Not Look Like a Snowman
- Versatile Dresses: How to Wear One Dress, Many Ways
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I hoped you liked these skirt outfits for cold weather. Please share with your friends on Facebook, Twitter, and Pinterest. Thanks for reading!
Author Bio: Sydney Woolery is a recent UCLA graduate who loves a good adventure just as much as she does a fabulous dress. Check out her fashion blog at www.tokyoglitter.com and follow her visual escapades on Instagram – @tokyoglitter.
These are very good skirt outfit ideas. Useful fashion tips. Thanks for sharing.
Just wear skin coloured stockings for a layer of warmth. It works a treat
Wow! I need this right now as I am going to Detroit tomorrow! As always, the travel tips are amazing! Thank you SO MUCH!!,
Thanks Cheryl 🙂
Thank you for this!!
Winter seems to never end and I miss my skirts!
I love wearing skirts. Unfortunately, I do have some skirts at home that are meant only for late spring or summer. I do, however, have a few skirts and dresses that I can wear with leggings on a cold day, or without on a hot day and they look good either way. They tend to be darker-colored or black dresses that fall to the knee. I also love wearing maxis year-round as well!
Great tips and I love how you beautifully styled all the pieces together ?
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