17 Chic Winter Skirt Outfits With Sweaters and Boots

Wearing skirts in winter can feel a little tricky when the weather gets cold, but you don’t have to pack away your favorite pieces until spring. With cozy sweaters, warm tights, and the right boots, skirts can be just as comfortable as jeans or trousers.

From elegant wool midi skirts to cute pleated minis and soft knit styles, there are plenty of ways to make them work for everyday plans.

These winter skirt outfits are perfect for coffee dates, work, church, weekend outings, and those days when you want to look a little more dressed up.

1. Chocolate Wool Midi Skirt & Cream Cable-Knit Sweater

A chocolate wool midi skirt with a cream cable-knit sweater creates a cozy, elegant outfit for chilly winter days. The soft neutral colors feel timeless, while the long coat and suede boots add warmth for a Sunday lunch or casual afternoon outing.

Outfit Pieces

1. Sweater: Cream chunky cable-knit turtleneck.
2. Skirt: Chocolate brown high-waisted A-line wool midi skirt.
3. Boots: Dark brown suede knee-high low block-heel boots.
4. Coat: Long camel tailored wool coat.
5. Handbag: Structured chocolate brown leather shoulder bag.

Style Tip

Give the chunky sweater a small front tuck to show the skirt’s waist without making the outfit feel too fitted.

2. Burgundy Pleated Skirt & Black Cashmere Turtleneck

A burgundy pleated skirt with a black turtleneck creates a beautiful winter look that feels feminine and polished. The rich skirt color brings warmth to the outfit, while the fitted sweater and tall boots make it suitable for work, church, or dinner.

Outfit Pieces

1. Sweater: Black fitted cashmere turtleneck.
2. Skirt: Deep burgundy wool-blend pleated midi skirt.
3. Boots: Black leather knee-high low block-heel boots.
4. Coat: Long charcoal grey tailored wool coat.
5. Handbag: Small structured black leather handbag.

Style Tip

Tuck the turtleneck fully into the skirt and let the pleats fall naturally over the tops of your boots.

3. Grey Pleated Mini Skirt & Navy Cable-Knit Sweater

A grey pleated mini skirt with a navy sweater creates a cute winter outfit with a classic preppy feel. The white shirt adds a polished touch, while the warm tights and tall boots make the shorter skirt easier to wear on chilly days.

Outfit Pieces

1. Sweater: Navy oversized chunky cable-knit crewneck.
2. Shirt: White cotton collared button-front shirt.
3. Skirt: Charcoal grey wool-blend pleated mini skirt.
4. Tights: Black opaque fleece-lined tights.
5. Accessories: Black leather knee-high flat boots and a small black leather crossbody bag.

Style Tip

Let the white shirt collar show above the sweater and keep the sweater slightly loose over the pleated skirt.

4. Black Satin Midi Skirt & Oatmeal Knit Sweater

A black satin midi skirt with an oatmeal sweater creates a soft, elegant outfit for winter. The smooth satin looks beautiful against the cozy knit, while the heeled ankle boots make the combination perfect for dinner, brunch, or a casual evening out.

Outfit Pieces

1. Sweater: Oatmeal relaxed-fit cashmere-blend crewneck.
2. Skirt: Black satin bias-cut midi skirt.
3. Boots: Black leather pointed-toe heeled ankle boots.
4. Coat: Long black tailored wool coat.
5. Handbag: Small chocolate brown leather shoulder bag.

Style Tip

Give the sweater a gentle front tuck and let the satin skirt fall naturally for a relaxed but elegant finish.

5. Cream Knit Midi Skirt & Chocolate Ribbed Cardigan

A cream knit midi skirt with a chocolate cardigan creates a warm, comfortable winter outfit that still feels feminine. The matching knit textures make the combination cozy, while the brown boots and camel coat add a polished finish.

Outfit Pieces

1. Cardigan: Chocolate brown chunky ribbed button-front cardigan.
2. Skirt: Cream high-waisted ribbed knit A-line midi skirt.
3. Boots: Dark brown leather knee-high low block-heel boots.
4. Coat: Camel wool-blend wrap coat.
5. Handbag: Small caramel leather shoulder bag.

Style Tip

Button the cardigan neatly and give it a slight front tuck to create some shape above the knit skirt.

6. Black Leather Midi Skirt & Grey Turtleneck Sweater

A black leather midi skirt with a grey turtleneck creates a chic winter outfit with a slightly edgy feel. The soft sweater balances the leather, while the tall boots and wool coat make the look comfortable for colder days.

Outfit Pieces

1. Sweater: Heather grey fitted ribbed turtleneck.
2. Skirt: Black high-waisted faux-leather A-line midi skirt.
3. Boots: Black leather knee-high low block-heel boots.
4. Coat: Long charcoal grey wool coat.
5. Handbag: Small black structured shoulder bag.

Style Tip

Keep the grey turtleneck tucked into the skirt and wear the coat open to show the contrast between the soft knit and leather.

7. Forest Green Wool Skirt & Ivory Cashmere Sweater

A forest green wool skirt with an ivory sweater creates a beautiful winter outfit with rich, classic colors. The soft cashmere and warm wool skirt make it comfortable for work or church, while the brown boots bring the whole look together.

Outfit Pieces

1. Sweater: Ivory fitted cashmere mock-neck.
2. Skirt: Forest green high-waisted wool-blend A-line midi skirt.
3. Boots: Chocolate brown leather knee-high low block-heel boots.
4. Coat: Long beige tailored wool coat.
5. Handbag: Structured dark brown leather top-handle handbag.

Style Tip

Keep the sweater fully tucked into the skirt and let the beige coat frame the green and ivory pieces.

8. Brown Suede Mini Skirt & Cream Chunky Sweater

A brown suede mini skirt with a cream chunky sweater creates a cute winter outfit with a cozy, slightly vintage feel. The warm tights and knee-high boots make the shorter skirt easier to wear, while the camel coat adds another comfortable layer.

Outfit Pieces

1. Sweater: Cream oversized chunky cable-knit turtleneck.
2. Skirt: Chocolate brown faux-suede A-line mini skirt.
3. Tights: Dark brown opaque fleece-lined tights.
4. Boots: Chocolate brown suede knee-high low block-heel boots.
5. Accessories: Long camel wool coat and a small tan leather crossbody bag.

Style Tip

Let the chunky sweater sit loosely over the skirt and keep the brown tights close in color to the boots.

9. Navy Pleated Midi Skirt & Burgundy Knit Sweater

A navy pleated skirt with a burgundy sweater creates a polished outfit using two beautiful winter colors. The pleated midi skirt feels feminine, while the fitted sweater and tall boots make the combination comfortable for church, work, or a nice lunch.

Outfit Pieces

1. Sweater: Burgundy fitted wool-blend crewneck.
2. Skirt: Navy high-waisted pleated wool midi skirt.
3. Boots: Black leather knee-high low block-heel boots.
4. Coat: Long charcoal grey tailored wool coat.
5. Handbag: Structured black leather handbag.

Style Tip

Keep the burgundy sweater tucked into the skirt so the pleats create a clean, flowing shape.

10. Chocolate Satin Skirt & Black Fitted Turtleneck

A chocolate satin skirt with a black turtleneck creates an elegant outfit for a winter dinner or evening date. The silky skirt adds a dressy touch, while the fitted knit sweater and wool coat keep the look warm and comfortable.

Outfit Pieces

1. Sweater: Black fitted cashmere turtleneck.
2. Skirt: Chocolate brown satin bias-cut midi skirt.
3. Boots: Black leather pointed-toe heeled ankle boots.
4. Coat: Long camel tailored wool coat.
5. Clutch: Small dark brown leather clutch bag.

Style Tip

Tuck the black turtleneck neatly into the skirt and let the satin fabric fall naturally around the boots.

11. Grey Knit Midi Skirt & Black Oversized Sweater

A grey knit midi skirt with a black oversized sweater creates a cozy outfit that feels relaxed but still polished. The soft knit fabrics make it comfortable for everyday plans, while the long coat and flat boots add warmth.

Outfit Pieces

1. Sweater: Black oversized chunky ribbed crewneck sweater.
2. Skirt: Heather grey high-waisted ribbed knit midi skirt with a small side slit.
3. Boots: Black leather knee-high flat boots.
4. Coat: Long black tailored wool coat.
5. Handbag: Small charcoal grey leather shoulder bag.

Style Tip

Give the oversized sweater a small front tuck to show the skirt’s waist without losing its cozy shape.

12. Burgundy Leather Mini Skirt & Grey Knit Cardigan

A burgundy leather mini skirt with a grey cardigan creates a cute winter outfit with a little edge. The soft cardigan balances the leather skirt, while the thermal tights and tall boots make the outfit practical for chilly afternoons or casual dinner plans.

Outfit Pieces

1. Cardigan: Heather grey chunky button-front knit cardigan.
2. Top: Black fitted long-sleeve thermal top.
3. Skirt: Burgundy high-waisted faux-leather A-line mini skirt.
4. Tights: Black opaque fleece-lined tights.
5. Accessories: Black leather knee-high low block-heel boots and a small black leather shoulder bag.

Style Tip

Wear the cardigan partly buttoned and let the burgundy skirt add color to the grey and black layers.

13. Camel Wool Skirt & Navy Fitted Sweater

A camel wool skirt with a navy sweater creates a classic winter outfit that feels refined without being too dressy. The deep navy and camel colors look beautiful together, while the knee-high boots and long coat make it a practical choice for work or weekend outings.

Outfit Pieces

1. Sweater: Navy fitted cashmere turtleneck.
2. Skirt: Camel high-waisted wool-blend A-line midi skirt.
3. Boots: Dark brown leather knee-high low block-heel boots.
4. Coat: Long chocolate brown tailored wool coat.
5. Handbag: Structured tan leather top-handle handbag.

Style Tip

Keep the navy sweater tucked into the skirt and wear the chocolate coat open to show the clean color combination.

14. Black Denim Maxi Skirt & Cream Mock-Neck Sweater

A black denim maxi skirt with a cream sweater creates a relaxed winter outfit that’s perfect for casual days. The denim gives the look a slightly edgy feel, while the chunky sweater, quilted jacket, and Chelsea boots keep it comfortable for errands or weekend plans.

Outfit Pieces

1. Sweater: Cream oversized chunky mock-neck sweater.
2. Skirt: Washed black high-waisted denim maxi skirt with a front slit.
3. Boots: Black leather chunky flat Chelsea boots.
4. Jacket: Olive green insulated quilted hip-length jacket.
5. Bag: Small black nylon crossbody bag.

Style Tip

Give the sweater a slight front tuck and choose a denim skirt with enough room at the hem for comfortable walking.

15. Dusty Blue Pleated Skirt & Ivory Ribbed Turtleneck

A dusty blue pleated skirt with an ivory turtleneck creates a soft, feminine winter outfit that feels fresh and elegant. The muted blue looks beautiful with cream and grey, while the tall boots and wool coat make it comfortable for a chilly day.

Outfit Pieces

1. Sweater: Ivory fitted ribbed turtleneck.
2. Skirt: Dusty blue wool-blend pleated midi skirt.
3. Boots: Taupe suede knee-high low block-heel boots.
4. Coat: Long light grey tailored wool coat.
5. Handbag: Small beige structured leather handbag.

Style Tip

Keep the ivory sweater tucked neatly into the skirt and let the light grey coat frame the soft blue color.

16. Olive Green Midi Skirt & Chocolate Cable-Knit Sweater

An olive green midi skirt with a chocolate sweater creates a beautiful winter outfit with earthy colors. The chunky knit adds warmth and texture, while the camel coat and dark brown boots give the combination a classic finish.

Outfit Pieces

1. Sweater: Chocolate brown chunky cable-knit crewneck.
2. Skirt: Olive green high-waisted wool-blend A-line midi skirt.
3. Boots: Dark brown leather knee-high low block-heel boots.
4. Coat: Long camel tailored wool coat.
5. Handbag: Small caramel leather shoulder bag.

Style Tip

Keep the sweater slightly tucked at the front and let the olive skirt fall naturally over the boots.

17. Black Pleated Midi Skirt & Burgundy Cashmere Sweater

A black pleated skirt with a burgundy cashmere sweater creates a timeless winter outfit that feels elegant and comfortable. The rich burgundy knit makes the black skirt look more interesting, while the tall boots and wool coat provide warmth for dinner, church, or a special afternoon outing.

Outfit Pieces

1. Sweater: Deep burgundy fitted cashmere crewneck.
2. Skirt: Black high-waisted wool-blend pleated midi skirt.
3. Boots: Black leather knee-high low block-heel boots.
4. Coat: Long charcoal grey wool wrap coat.
5. Accessories: Structured black leather handbag and delicate gold stud earrings.

Style Tip

Tuck the cashmere sweater fully into the skirt and keep the accessories simple so the burgundy and black combination remains the focus.