Your Girl Knows’ product recommendations are handpicked by our editorial team and given the seal of approval by Harman herself. When you buy something through our affiliate links, we might earn a little commission—at no extra cost to you! We only recommend products we genuinely love. Please read my Disclosure Policy for additional information.
Can you believe that winter is just around the corner? I know, I know, it’s a love-hate relationship with the frosty season. But let me tell you a little secret: there is no need to bid adieu to your fave skirts when the temperature drops!
I’m here to spill the tea on how to style those fabulous skirts for a warm and chic winter wardrobe. So, buckle up, ’cause you’re about to embark on a whirlwind (or should I say snowstorm?) journey filled with cool tips and snazzy winter skirt outfit ideas.
Are you ready to rock the skirt trend? Let’s dive in! ❄️✨
38 Cutest Winter Skirt Outfits You’ll Ever See!!
1. oversized knit sweater + maxi skirt
Bundle up in style with this oversized knit brown sweater paired with a maxi beige skirt. This combo is not only cozy, but also super chic! Top it off with some white sneakers, and girl, you’re ready to conquer any winter wonderland!
Get The Look
2. checkered sweater + maxi skirt with slit
Gingham all the way, hun! Turn heads with this gray and white checkered sweater and maxi white skirt with a slit combo. Rock it with some metallic flats for added warmth and BAM! You’ve got yourself a show-stopping winter outfit.
Get The Look
3. trench coat + turtleneck + flared skirt
Channel your inner fashion diva with this classy caramel long trench coat, black turtleneck, and black pleated skirt ensemble. This look screams sophisticated style. Strut your stuff in some chic leather boots and you’re good to go!
I specifically love this mini skirt outfit for winter solely because it makes you look expensive and old money, haha. Sleek, minimal, sexy.
Get The Look
4. Striped cardigan + satin midi skirt
Get ready to slay in this fab combo. Throw on a warm, eye-catching striped cardigan over a luxurious satin midi skirt for a cool, comfy, and chic look. Finish it off with your fave pair of flats, and you’re ready to hit the streets in style.
Get The Look
5. monochrome sweatie + denim skirt
Who says the cold season can’t be white-hot? This monochromatic outfit is an absolute stunner – just pair a cozy white sweatshirt with a long white denim skirt. Bring out your best white kicks, and you’ll be an ice queen turning heads wherever you go.
I’m totally living for the accessory match going on here. From red stripes in the shoes, to red bag and then red lettering over the sweatie!!
Get The Look
6. trench coat + sweater + pleated mini skirt
Monochrome magic, anyone? This gray trench coat, gray turtleneck sweater, and pleated mini skirt outfit for winter is all about keeping it fierce. Amp it up with black leather knee high boots for the ultimate winter power move. Talk about a total knockout!
Get The Look
7. sweater + mini skirt
You can’t go wrong with an all-black ensemble! Swaddle yourself in a black sweater, black mini skirt, and stockings to create a sleek, stunning winter outfit. Add some ankle boots and a statement necklace to really make this look pop!
Get The Look
8. cardigan over shirt + mini skirt
Try a classic white cardigan over a light blue shirt, paired with a black mini skirt. This outfit is perfect for a casual yet polished look. Keep it cute with some black stockings and knee length boots to complete your fab winter wardrobe!
Get The Look
9. sweater + maxi skirt with slit
More than summer, this is the most perfect time to rock your long skirts. This combo of a cozy green sweater and a sexy black maxi skirt with a slit will make you feel like you’re strutting down the runway, even in the coldest weather.
And don’t forget my biggest styling tip to dress simple and stylish – Match your accessories, honey! 😉
Get The Look
10. turtleneck oversized sweater + midi skirt
Who says you can’t rock a killer midi skirt in winter? Bundle up in style with a cozy cream turtleneck oversized sweater paired with a chic beige midi skirt. Finish off this super cute look with white sneakers for a casual yet oh-so-classy vibe.
Get The Look
11. sweater over shirt + mini skirt
Ooh, check out this stylish layered look! A black sweater over a white shirt paired with a cute gray mini skirt and stockings will have you looking fab no matter what the winter weather throws at you.
Of course, fleece-lined stockings and combat boots are a must-have for winter mini skirt outfits, isn’t it?
12. turtleneck crop sweater + checkered skirt
Gingham goodness! Pair a cream turtleneck crop sweater with a cute, checkered skirt, and finish the look with knee-high cream boots for a cozy and adorable outfit perfect for brunch dates.
Idk about you, but I especially love the knee-high socks peeking through the boots. Gives a very preppy girl vibe!
Get The Look
13. turtleneck top + maxi denim skirt
Denim skirts are the epitome of effortlessly cool vibe! A black turtleneck top with a maxi blue denim skirt and knee-high black boots will give you major indie vibes while keeping you warm and comfy.
Of course, match the colour of your belt, bag and sunglasses to your boots and you’ll keep those heads turning for ya with this long skirt outfit for winter!
Get The Look
14. turtle neck + leather jacket + leather skirt
Who said leather on leather’s a no-go? Break the rules and strut in this daring but one of the trendiest long skirt outfits for winter! A sleek turtleneck + leather jacket + leather skirt trio spells effortless chic, just like that! 💅
Fashion Tip: Mix it up with different textures, like suede or croc-embossed. Variety keeps things edgy and fun!
15. oversized sweater over a dress
Surprise! That flowy summer dress can work for winter too—just zhuzh it up! Pop an oversized sweater over your dress and BAM, you’ve got a new skirt! Add tights, ankle boots, and voila—cuteness overload!
You can also add colourful scarves and a beanie for extra warmth and style points.
Get The Look
16. oversized v-neck sweater + mini skirt
Minimalist chic! Pair an oversized beige V-neck sweater with a black mini skirt for an effortlessly fashionable outfit that’s just as perfect for a cozy day indoors as it is for a night out on the town.
Get The Look
17. sweater vest + tennis skirt
Sporty vibes, anyone? This white sweater vest over a black turtleneck top paired with a black tennis skirt is ace for any athleisure-loving fashionista. Layer a V-chain necklace over to kill the boxy style and make yourself look taller!
Get The Look
18. leather jacket + tank top + maxi denim skirt
Slay in this bold, edgy outfit! The black leather jacket and knee-high boots scream “fierce”, while the maxi denim skirt adds a fun, casual twist. Totally badass!
Get The Look
19. shirt + pleated skirt
Rock the preppy-chic look with this graceful combo. Layer a blue shirt over a gray turtleneck top and pair it with a matching mini-pleated skirt for a polished and sophisticated look!
I have to admit, this is one of the most stylish and unique winter skirt outfits with boots out there! And it follows my other great styling tip – never add more than 3 colors to an attire. Black & white are excluded!
Get The Look
20. pullover over shirt + maxi skirt
The perfect ensemble for cozying up on those chilly days! Layer a pullover sweater over a classic white tee and pair it with a maxi skirt in a complementary color. Don’t forget to rock some tall boots to keep your legs warm and make the outfit extra fab. You’ll be the definition of cozy-chic!
Get The Look
21. striped sweatshirt + pleated skirt
Add a touch of playfulness to your winter wardrobe with this lively combo. Pair a fun striped sweatshirt with a flirty pleated skirt and throw in some seriously snuggly fleece-lined stockings for ultimate comfort. Your winter style just got a major upgrade!
22. monochrome outfit
Go all-out, snow queen, in this wintry white ensemble! Embrace the monochromatic trend with this sleek outfit, and be ready to turn heads wherever you go.
Get The Look
23. sweater vest + pleated skirt
Mixing textures has never looked this chic! The white-lined gray sweater vest paired with a black turtleneck and pleated skirt brings a trendy edge to your winter wardrobe. Don’t forget the knee length boots for a fashion-forward finish!
24. oversized sweatshirt + pleated skirt
Get ready to slay in this sporty yet ultra-stylish outfit. The oversized sweatshirt adds a comfy, laid back vibe, while the mini pleated skirt gives it a flirty twist. Top it off with a coordinating cap and white sneakers, and you’re good to go!
Get The Look
25. Oversized sweater + maxi skirt + leather jacket
Turn up the heat with this killer combo: an oversized sweater that you can style by tucking in or leaving untucked, paired with a super hot maxi skirt. Throw on a fierce bombshell bomber leather jacket to keep you warm and lookin’ fly. Compliment the look with some cool sneakers or ankle boots and you’re all set to slay, girl!
Get The Look
26. turtleneck sweater + mini leather skirt
Bring some warmth to your winter attire with this snuggly combo. The ribbed turtleneck sweater keeps you cozy, and the brown leather skirt adds a touch of elegance. Strut in style with those white strappy heels, hun!
Get The Look
27. oversized sweatshirt + pleated mini skirt
Nail the cozy-meets-cute look in this dreamy mini skirt outfit for winter! The oversized sweatshirt works perfectly with the gray pleated skirt, and the black knee-length boots tie it all together. Stay warm and fab, darling!
Get The Look
28. cardigan + midi leather skirt
Classic and chic, this combo is perfect for both work and play. The cream cardigan adds a touch of sophistication, while the midi leather skirt and knee-high boots create a sleek, polished look. Looking flawless, girl!
Get The Look
29. pastel sweater + tennis skirt
If you’re a sucker for pastels, this combo will make you swoon. Pair a cozy pastel green knit sweater with a crisp white tennis skirt. Add white knee-length boots to keep those legs warm and cool-as-ice.
Get The Look
30. leather jacket + maxi denim skirt
Get rebelliously chic in this fit; rock a black leather jacket over a black maxi denim skirt. Kick it up with some cool sneakers and voila – you’ve got the baddest outfit in town!
Get The Look
31. oversized sweater + tennis skirt
Stay sophisticated and snug in this monochromatic dream. Layer a black oversized sweater over a white button-down shirt and pair it with a white tennis skirt.
Get The Look
32. puffer jacket + turtleneck + midi denim skirt
Puff it up with this toasty ensemble! Pair a black puffer jacket with a black turtleneck and a washed blue midi denim skirt – the epitome of casual winter skirts for a totally comfy and stylish look.
33. fleece top + pleated mini skirt
Fleece is the word, ladies! Keep it cozy and cute in this brown fleece top paired with a matching brown pleated mini skirt. Your winter wardrobe will thank you!
Get The Look
34. oversized blazer over crop shirt + mini skirt
Why not rock a blazer like a boss? Layer a gray oversized blazer over a blue crop shirt and white tee, and strut your stuff in a sleek black mini skirt.
35. sweatshirt + barbie mini skirt
Let your inner Barbie shine in this pop-tacular outfit! Mix a graphic gray sweatshirt with a super cute pink mini skirt and stand out from the crowd!
Get The Look
36. oversized jacket + plaid mini skirt
Nobody can resist a good plaid moment in winter. Throw on an oversized black jacket over a white tee, slip into a plaid mini skirt, and add a pair of stockings to complete this timeless look!
37. sweater + maxi denim skirt
Yeehaw! Embrace your inner cowgal with a cozy gray sweater, a blue maxi denim skirt, and top it off with some killer black cowboy boots.
38. sweater vest + turtleneck + mini skirt
How about some preppy vibes? Pair a timeless caramel sweater vest with a black turtleneck and a black mini skirt for a fashion-forward look. You can also try wearing some toasty stockings if you like.
I’d pair this winter skirt outfit with stockings and ankle boots because who likes to freeze to death, haha?
Get The Look
Final thoughts on winter skirt outfit ideas
So there you have it, fab friends! Winter skirts are not a fashion faux pas but a winter wonderland wardrobe staple. Who said you could only strut your stuff in skirts during the warmer months?
With these amaze tips and tricks, you’ll be breakin’ hearts and turning heads all season long. 💁♀️❄️💕
Now, I’d love to hear from you! Share your winter skirt #OOTDs, your go-to combos, and any other style secrets you have up your warm, cozy sleeves.
Together, we’ll keep slaying the game and looking stunning even when the weather outside is frightful. Drop your comments below, and don’t forget to share this post with your fellow fashionistas to keep the winter skirt trend going strong! xo
Related articles on winter skirt outfits
- 31 Super Cute Winter Outfits That Are To Die For (Not Kidding!)
- 32 Baddie Winter Outfits That Are HOT & Won’t Let You Freeze
- 45 UGGs Outfits To Keep You Lookin’ Fly And Feelin’ Toasty!
- 37 Trendy Winter Nail Designs To Get Flooded With Compliments
- 27 Chunky Loafers Outfits That’s Taken The ‘Gram By Storm
