22 Chic Plus Size Winter Outfits With Short Skirts That Make a Statement

Winter outfits with short skirts have become one of my favorite little style secrets because they always make me feel bold even on the chilliest days.

I love how a good mini paired with the right cozy layers creates that perfect mix of cute and confident.

There is something so fun about building a look that feels warm but still shows a little personality.

If you’re into pieces that turn heads in the best way this list might inspire your next cold weather outfit.

No matter your style I’m sharing the looks that make me feel chic comfortable and ready to pretend I am not freezing at all.

Cozy Teddy Jacket With a Textured Mini Skirt

This outfit pairs a soft beige teddy jacket with a textured knit mini skirt that feels perfectly wintry and effortlessly cute. The jacket brings that warm and plush look we all adore once the weather turns chilly while the skirt adds a structured contrast with its deep charcoal tone and cozy knitted feel. Sheer black tights keep everything season appropriate and the lace up combat boots ground the look with a little edge. The whole vibe feels like a confident winter stroll through the city where comfort and style agree to team up.

I love how this outfit mixes cozy and chic because it feels like something I would wear on a weekend outing when I want to look put together without trying too hard. The teddy jacket adds such a flattering softness up top and the shorter skirt keeps the silhouette fresh and fun. The tights are a great trick for warmth and the boots pull the whole look together with a bit of attitude. It is one of those combinations that makes you feel warm but still stylish which is a winter win in my book.

Edgy Street Style With a Leather Jacket and Ribbed Mini Skirt

This look mixes a classic black faux leather biker jacket with a charcoal ribbed knit mini skirt that gives just the right amount of texture for winter. The black V neck top keeps everything simple and streamlined while sheer tights and chunky black ankle boots add that cool city girl vibe we all secretly want to channel on a chilly morning. The gold earrings and crossbody bag add a soft touch that balances the boldness of the leather and keeps the outfit feeling polished rather than too intense.

I love how this outfit gives me that confident walk down the sidewalk feeling because it blends comfort and attitude in such an easy way. The mini skirt shows a little leg without feeling exposed thanks to the tights. The jacket adds structure without making me feel boxed in. It looks chic because it plays with contrast and texture while still staying totally wearable for everyday winter errands or a casual meet up.

Colorblock Sweater With a Denim Mini Moment

This outfit mixes a bold navy, mustard, and cream colorblock sweater with a classic denim mini skirt that feels playful yet winter ready. The cozy knit brings warmth without looking bulky while the skirt adds that cute leg lengthening effect we all love. Black tights keep everything practical for chilly days and the tan lace up winter boots give the look a grounded city girl energy. The whole outfit feels vibrant and fun with just the right touch of casual confidence.

I love this look because it feels effortless in the best way. The colorblock sweater does all the heavy lifting and instantly brightens the outfit while the denim mini balances things with a little structure. The tights make the short skirt feel wearable even when the weather is not on our side and the boots add this warm rustic charm that keeps everything from feeling too sweet. It is one of those outfits that makes me feel cute and comfortable at the same time which is basically the winter dream.

Plaid Mini Skirt With a Cozy Green Turtleneck

This outfit pairs a fitted forest green turtleneck with a soft wool plaid mini skirt that brings in rich winter tones of charcoal, red, and cream. The black tights keep everything warm and polished while the ankle boots add that confident city stride vibe. The tan crossbody bag pulls the look together with a warm touch that feels effortless for a crisp winter walk. The whole outfit has that perfect everyday charm where comfort meets cute in the best way.

I love how this look feels both simple and put together because it is the kind of outfit I reach for when I want to feel warm but still look like I tried. The fitted turtleneck balances the structure of the skirt so nicely and the dark tights make everything feel sleek and flattering. The plaid adds personality without overwhelming the outfit and the crossbody bag gives me that hands free freedom that just makes winter days easier. It is chic without feeling fussy and that is always a win for me.

Cozy Cable Knit Sweater With a Forest Green Mini Skirt

This look pairs a soft ivory cable knit sweater with a cute forest green corduroy mini skirt that feels perfectly winter ready without losing that playful short skirt charm. The tights add a layer of warmth while keeping the outfit sleek and smooth. The cozy knit brings texture while the skirt adds a pop of rich color that feels right at home against a snowy backdrop. The whole outfit has that sweet mix of comfy and polished that makes winter dressing feel fun again.

I love how this outfit finds that sweet spot between warm and stylish because it makes me feel put together without trying too hard. The chunky knit balances the shorter skirt so everything feels flattering and effortless. I also like how the deep green stands out in such a simple way. It feels like one of those everyday winter looks you reach for again and again because it just works and it always feels cute.

Cozy Chunky Cardigan With a Sleek Black Mini

This look pairs a soft chunky gray cardigan with a fitted black mini dress that has a subtle ruched detail through the front. The mix of textures feels perfect for winter since the knit adds warmth while the dress keeps everything sleek and put together. Black tights and simple black ankle boots keep the outfit clean and balanced and the structured black handbag adds a little polish without taking away from the cozy vibe. The whole look feels relaxed but still very intentional which makes it such a great cold weather go to.

I love how this outfit lets me stay comfortable without losing that chic little edge. The oversized cardigan gives me that snug wrapped up feeling but the short skirt keeps the outfit fun and confident. The tights make the look feel season friendly and the monochrome base underneath the knit is incredibly flattering. It is the kind of outfit that makes winter actually exciting because it feels easy warm and stylish all at once.

Cozy Black Knit With a Classic Plaid Mini

This outfit pairs a soft black knit sweater with a timeless plaid mini skirt that instantly feels winter ready. The thick fabric of the sweater adds a warm and snuggly vibe while the skirt brings a structured shape that looks polished without feeling fussy. Black tights keep everything sleek and season appropriate and the ankle boots add that little confident kick we all love on a cold morning. A simple crossbody bag finishes the look with easy everyday practicality.

I love how balanced this outfit feels because the cozy sweater gives that relaxed comfort while the plaid skirt adds just the right amount of personality. The dark tights help everything flow together so the silhouette feels smooth and flattering. It is one of those looks that makes me feel put together without trying too hard and honestly that is the dream in winter dressing.

Cozy Red Sweater Dress With a Peekaboo Plaid Skirt

This look is such a winter charmer with its bright red sweater dress that feels warm and soft without looking bulky. The hemline gives a playful peek at a black and red plaid mini skirt that adds a cute little pop of pattern. Paired with navy tights, tall brown leather boots, and a chunky knit hat and scarf in a warm taupe shade, the whole outfit feels perfectly put together for a snowy stroll. The textures are rich, the colors are bold, and the vibe gives cheerful holiday energy in the best possible way.

I love how this outfit balances comfort and cuteness because the sweater dress keeps everything cozy while the short plaid skirt adds just the right amount of statement flair. The mix of textures feels really flattering and the bold red always photographs beautifully. The tall boots give structure to the look and the knit accessories make it feel extra winter ready. It is the kind of outfit that makes you feel adorable and confident even on the chilliest days.

Creamy Cable Knit With an Emerald Mini

This look is such a winter mood with its chunky cream cable knit sweater paired with a deep emerald mini skirt that adds the perfect pop of rich color. The sweater feels soft and cozy while the skirt brings a sleek, slightly dressy vibe that makes the whole outfit feel polished without trying too hard. Black semi sheer tights and ankle boots keep everything grounded and cold weather friendly while still showing off the playful length of the skirt. The overall feel is warm, chic, and effortlessly confident.

I love how this outfit balances comfort and style because it feels like something I could wear all day without a single adjustment. The oversized knit gives that relaxed winter coziness while the emerald mini adds a fun little sparkle that makes the outfit feel intentional. The tights smooth everything out and make the skirt feel wearable even on chilly days. It is the kind of look that turns a simple winter walk into a cute moment and makes me feel put together in the easiest way.

Navy Sweater With a Sleek Winter Mini

This outfit feels like the perfect mix of cozy and polished. The deep navy chunky knit sweater brings that warm, snuggly vibe we all crave in winter while still looking totally put together. It’s paired with a simple gray A line mini skirt that adds a soft structured feel without being stiff. The black tights keep things sleek and weather friendly, and the shiny ankle boots add a little city chic energy that makes the whole look feel intentional. The brown crossbody bag brings in a warm touch that softens the cool tones of the outfit and ties everything together effortlessly.

I love how this look manages to be warm, comfortable, and polished all at the same time. The sweater gives that easy relaxed mood while the mini skirt keeps the outfit feeling fun and feminine. The dark tights and ankle boots streamline the legs and add a little boost of confidence that always feels great on chilly days. This combo works so well because it’s simple but still stylish and it has that everyday wearable charm that never gets old.

Cozy Neutrals With a Teddy Coat Moment

This look is all about warm winter neutrals that still feel polished and put together. The soft ribbed knit sweater dress creates a smooth and comfortable base while the knee-skimming length keeps it playful and feminine. Layered on top is a plush teddy coat in a gorgeous camel shade that instantly adds texture and that snug bundled-up vibe we all crave when the air gets frosty. The heeled ankle boots match the neutral palette and keep the outfit sleek while the gold earrings bring a hint of sparkle that feels effortless. The whole outfit has this quiet confidence that feels chic without even trying.

I love how this look blends comfort and style in such an easy way because the knit dress hugs in all the right places while still feeling cozy enough for real winter weather. The longer coat keeps everything balanced so the shorter skirt never feels too exposed and the monochromatic colors make the whole outfit look elevated. It is one of those outfits that makes me feel warm, stylish, and totally put together even on the chilliest days.

Chic Trench Coat With a Winter Mini

This look brings together a soft taupe mini skirt with cozy tights and a sleek black ribbed turtleneck that keeps everything feeling warm and polished. The classic beige trench coat adds that effortlessly stylish outer layer that always makes a simple outfit look instantly elevated. Paired with cream ankle boots and a natural, fresh vibe, the whole look feels city chic in the best way.

I love how this outfit creates such a clean and flattering silhouette without trying too hard. The turtleneck smooths everything out, the mini skirt brings a playful touch, and the trench pulls it all together with that timeless flair we all adore. It feels confident, feminine, and easy to wear on those chilly days when you still want to look cute strolling through town.

Cozy Forest Green Sweater With a Charcoal Wrap Skirt

This outfit brings together a chunky forest green turtleneck sweater with that soft, cocoon-like knit everyone wishes they could live in once winter hits. It pairs beautifully with a charcoal wrap skirt that has a subtle tailoring vibe and a sweet side tie that adds just enough interest. Dark tights and over-the-knee boots keep the legs warm while still letting the short skirt shine. A simple black crossbody bag finishes the look with an easy everyday feel. The whole outfit has this relaxed yet put-together charm that works perfectly with snowy winter scenery.

I love how this look manages to feel warm and polished at the same time. The oversized knit adds that cozy comfort we all crave, while the structured wrap skirt keeps the outfit from feeling bulky. The tall boots create a nice long line on the legs and balance the heavier sweater on top. It is the kind of winter outfit I would wear on repeat because it feels stylish without trying too hard and flattering in a way that makes you want to take a little winter stroll just like this.

Bold Red Sweater With a Playful Winter Mini

This outfit pairs a bright cherry red turtleneck sweater with a classic black pleated mini skirt that moves beautifully with every step. The black tights keep things warm while the chunky lace up boots and cozy knit leg warmers add that cute winter energy we all love. The mix of soft knit textures and structured pleats creates a look that feels both polished and fun which makes it perfect for a cold day in the city.

I love how this look feels so confident without trying too hard. The pop of red instantly lifts the mood and adds a little festive flair while the black skirt and boots keep everything grounded and flattering. The leg warmers are such a cozy touch and they make the whole outfit feel more intentional. It is the kind of winter outfit that makes you feel warm stylish and genuinely happy to step outside.

Camel Coat With a Sleek All Black Mini Look

This outfit is such a winter classic with a chic twist. The warm camel coat instantly stands out with its soft tailored structure and clean lapels. Underneath, the fitted black turtleneck pairs perfectly with the flared black mini skirt, creating that effortless mix of polished and playful. The sheer black tights pull the whole look together while the black leather bag and loafers add a smart finishing touch. The overall vibe feels modern city girl who knows exactly how to stay warm without hiding her shape.

I love how this outfit balances comfort and confidence because the camel coat softens the all black base in the most flattering way. The mini skirt gives just enough movement to feel fun while the tights make it feel totally winter ready. I also adore how the coat frames the silhouette without clinging. It creates that magic combination of warmth, ease and style that always photographs beautifully and feels even better in person.

Cozy Cable Knit With a Warm Winter Mini

This look blends a soft cream cable knit sweater with a warm caramel mini skirt that instantly feels perfect for a crisp winter stroll. The chunky knit adds that cozy texture we all crave while the skirt brings a pretty touch of movement. Black tights keep everything sleek and warm and the tall brown boots add a polished finish that ties all the earthy tones together. The little crossbody bag in a matching brown shade makes the whole outfit feel easy and put together without trying too hard.

I love how this outfit finds that sweet spot between comfort and style because it feels like something I would throw on for a coffee run and still feel adorable in. The sweater sits in that flattering middle ground where it feels relaxed but still intentional and the mini skirt brings a playful touch that keeps the outfit from looking too heavy. The matching brown accessories really help everything feel cohesive and the tall boots make my legs look longer which is always a win in my book.

Cozy Grey Knit With a Classic Black Mini

This look brings together a chunky grey knit sweater with that perfectly slouchy, winter loving vibe, paired with a matching knit scarf that instantly makes the whole outfit feel warm and soft. The black A line mini skirt creates a cute and flirty shape while still feeling polished, and the opaque black tights keep everything cozy for cold weather strolls. The black ankle boots and simple crossbody bag pull the outfit together in a clean and effortless way that feels very city chic.

I love how this outfit blends comfort with a little playful confidence because it feels stylish without trying too hard. The oversized grey knit balances the short skirt so well and gives the whole look a relaxed charm. The darker bottom half creates a long leg line that feels super flattering, and the textures make everything feel winter ready without looking bulky. It is the kind of outfit I would wear on repeat because it is warm, cute, easy, and gives that perfect cozy girl energy while still feeling put together.

Sophisticated City Look With a Warm Belted Coat

This outfit centers around a beautiful charcoal belted coat that instantly gives off that polished winter energy we all want on chilly mornings. Underneath, a textured mini skirt peeks out just enough to add some personality without overwhelming the look. The opaque tights keep everything sleek and warm while the black ankle boots add a little lift and make the whole outfit feel intentional. The soft waves, bold lip, and simple earrings finish things off with a touch of quiet confidence that looks right at home in the city.

I love how this look feels both practical and put together because sometimes winter outfits can feel bulky or shapeless. The belt cinches the waist in such a flattering way and the mix of structured outerwear with a short skirt gives that fun balance of cozy and chic. The dark tones elongate the silhouette while the mini skirt keeps things playful. It is one of those winter looks that makes me feel like I can walk down any street with my hands in my pockets and still look effortlessly stylish.

Soft Pink Knit With a Sleek Leather Mini

This outfit pairs a soft blush pink knit sweater with a sleek black faux leather mini skirt that instantly creates that perfect mix of cozy and cool. The chunky ribbed texture of the sweater feels warm and relaxed while the structured shine of the skirt brings a little edge to the look. Black sheer tights keep everything weather friendly and add a hint of polish. The chunky black ankle boots ground the outfit beautifully and give it that practical city girl vibe that looks effortlessly put together.

I love how this outfit makes a simple winter day feel a bit more fun. The contrast of the plush sweater with the leather skirt creates such a flattering balance and the pink adds a gentle pop of color without being loud. It is one of those outfits that feels comfortable enough for a long walk but still stylish enough for a coffee date. The proportions work so well and the textures make the whole look feel intentional and chic without trying too hard.

Black Puffer With a Bright Mustard Scarf

This outfit mixes cozy winter staples with a fun splash of color. The black puffer jacket has that soft, cloudlike feel while keeping things structured enough to look intentional. Underneath, the short black skirt and dark tights add a cute and simple base that lets the accessories shine. The chunky mustard scarf is the star of the look with its rich warm texture that instantly brightens the whole outfit. Paired with sturdy lace up winter boots and a sleek black bag, the overall vibe feels practical but still very put together for cold city days.

I love how this look feels both warm and playful because that pop of mustard adds personality without trying too hard. The short skirt keeps things light and feminine while the puffer gives the whole outfit a comfy protective feel that I always appreciate in winter. The contrast between the all black base and the bold scarf creates such a flattering balance that draws the eye upward and makes the outfit feel thoughtfully styled. It is exactly the type of winter look that makes me feel cute even when the temperature is not cooperating.

Cozy Teddy Jacket With a Sleek Black Mini

This outfit mixes the warmest teddy texture with the smooth shine of a black wrap style mini skirt. The soft caramel brown jacket feels plush and comforting, almost like wearing a hug on a chilly city day. Paired with sheer black tights, sleek ankle boots, and a simple black crossbody bag, the whole look feels modern and polished while still giving that effortless cool girl vibe. The balance of textures creates a really eye catching contrast that makes the skirt feel even more striking.

I love how this look gives major confidence without trying too hard. The fluffy jacket adds volume in such a flattering way and the short skirt brings that fun winter energy that always turns heads. The tights pull everything together while keeping the outfit practical for colder days. This is the kind of outfit that makes me feel instantly put together for a coffee run or a casual night out and it proves that plus size winter style can be both chic and comfortably warm at the same time.

White Fuzzy Jacket With a Sleek All Black Mini Look

This outfit blends that classic city girl energy with winter ready textures in the best way. The soft white fuzzy jacket instantly brightens the look and gives it that cozy polished feel while the fitted black mini dress underneath keeps everything streamlined and chic. The sheer tights add a touch of warmth without taking away from the clean silhouette and the black ankle boots make the whole outfit feel confident and modern. The little black shoulder bag and simple hoop earrings finish things off with a hint of effortless elegance that works beautifully for a busy day in the city.

I love how this look feels both bold and approachable at the same time. The contrast of the white jacket against the all black base creates such a striking balance and the fitted mini dress adds that little pinch of attitude we all want during winter. The boots keep the outfit practical for walking around while still looking sleek. Every piece works together to create a chic winter moment that feels flattering and super wearable.