17+ Chic Skirt Outfits Inspirations for Winter

Winter is here, and while it’s tempting to cozy up in joggers and oversized hoodies, let’s not forget the power of dressing up!

There’s something undeniably uplifting about slipping into a chic outfit that makes you feel confident and stylish, even when the temperatures drop.

Why settle for mundane loungewear when you can embrace the elegance of winter skirts?

Winter skirts are a versatile option that can be dressed up or down. From cozy turtlenecks paired with pleated skirts to sleek blazers over satin slips, the possibilities are endless.

So, what are you waiting for? Let’s dive into some chic winter skirt outfits that will have you looking fabulous all season long!

1. Oversized Leather Jacket + Mini Skirt + Knee-High Boots

Instagram: @watchingnewyork

A bold statement with an oversized leather jacket paired with a mini skirt and knee-high boots. This edgy ensemble is perfect for those who love to stand out.

Where to Wear: Ideal for concerts, night outs, or urban adventures.
Pair With: A studded bag for extra flair or a choker necklace for a punk touch.
Avoid: Delicate accessories that might get overshadowed by the boldness.

2. Black Turtleneck + Leather Pencil Skirt + Heels

Instagram: @doctor.clarissa

This outfit exudes elegance with a black turtleneck and a leather pencil skirt, complemented by classic heels.

It’s a timeless look that works for various occasions.

Where to Wear: Perfect for business meetings, dinners, or formal gatherings.
Pair With: A structured handbag for a polished look or pearl earrings for sophistication.
Avoid: Casual footwear that diminishes the formal appeal.

3. Puffer Jacket + Floral Mini Skirt + Ankle Boots

Instagram: @elainamich

A playful mix of a cozy puffer jacket with a floral mini skirt, finished with ankle boots. This combination is both fun and functional for colder days.

Where to Wear: Suitable for weekend getaways, brunches, or casual meet-ups.
Pair With: A knitted scarf for extra warmth or a backpack for practicality.
Avoid: Heavy accessories that can overwhelm the playful nature.

4. Black Sweater + Pleated Midi Skirt + Sandals

Instagram: @being_bridget

A classic black sweater paired with a pleated midi skirt creates a refined and versatile look.

The sandals add a touch of lightness, making it perfect for transitional weather.

Where to Wear: Great for garden parties, casual dinners, or art gallery visits.
Pair With: A belt to accentuate the waist or a statement necklace for a pop of color.
Avoid: Bulky outerwear that can hide the elegant silhouette.

5. Turtleneck Sweater + Mini Skirt + Belt + Riding Boots

Instagram: @annabelpesant

This outfit is a perfect blend of comfort and style. The grey cable knit sweater adds warmth, while the pleated mini skirt brings a playful touch.

The riding boots complete the look, making it ideal for a casual day out or a cozy coffee date.

I love how the belt cinches the waist, adding definition to the silhouette. This outfit shines during weekend brunches or casual outings with friends.

Where to Wear: Perfect for brunch, casual outings, or shopping trips.
Pair With: A crossbody bag for a laid-back vibe or statement earrings for a touch of glam.
Avoid: Heavy accessories that can overwhelm the look.

6. Cropped Trench + Black Maxi Skirt + Sneakers

Instagram: @dimamthini

This look combines a chic cropped trench coat with a sleek black maxi skirt, offering a perfect blend of casual and sophisticated.

The addition of sneakers keeps it comfortable and stylish for everyday wear.

Where to Wear: Great for casual outings, shopping trips, or coffee dates.
Pair With: A crossbody bag for a relaxed vibe or a beanie for added warmth.
Avoid: Overly formal shoes that clash with the casual elements.

7. Cropped Gray Jacket + Black Leather Skirt + Thigh-High Boots

Instagram: @trendina_eg

This edgy ensemble features a cropped gray jacket paired with a sleek black leather skirt and thigh-high boots, creating a bold and modern look.

Where to Wear: Perfect for city strolls, fashion events, or night outs.
Pair With: A structured clutch for a polished finish or bold sunglasses for added drama.
Avoid: Overly casual accessories that can detract from the sleek vibe.

8. Beige Blazer + Beige Turtleneck Sweater + Black Mini Skirt + Boots

Instagram: @mmequeenb

This outfit is all about layering and texture! The beige wool blazer over a matching turtleneck creates a chic monochromatic look, while the black mini skirt adds a playful contrast.

The riding boots keep the outfit grounded and practical for winter wear. This combination is perfect for a day at the office or a casual dinner with friends.

Where to Wear: Ideal for work, casual dinners, or coffee dates.
Pair With: A crossbody bag for a casual vibe or statement earrings for a pop of personality.
Avoid: Overly bright colors that can clash with the neutral palette.

9. Black Leather Jacket + White Midi Skirt + Mary Janes

Instagram: @mademoisellejaime

A sophisticated mix of a black leather jacket with a white midi skirt and classic Mary Janes. This outfit balances edgy and elegant elements seamlessly.

Where to Wear: Ideal for work meetings, gallery visits, or dinner dates.
Pair With: A minimalist handbag for a clean look or silver jewelry for a touch of shine.
Avoid: Bright colors that might clash with the monochrome palette.

10. Camel Coat + Black Knit Skirt + Chunky Boots

Instagram: @gotup_gotdressed

This cozy outfit combines a camel coat with a black knit skirt and chunky boots, offering warmth and style for colder days.

Where to Wear: Great for weekend brunches, shopping trips, or casual gatherings.
Pair With: A crossbody bag for convenience or a beanie for extra warmth.
Avoid: Delicate shoes that don’t match the chunky aesthetic.

11. Brown Knit Sweater + Leopard Print Skirt

Instagram: @taylor_deliman

This playful outfit features a cozy brown knit sweater with a leopard print skirt, perfect for adding a touch of fun to your winter wardrobe.

Where to Wear: Ideal for casual lunches, shopping sprees, or relaxed weekends.
Pair With: Simple hoop earrings for a chic touch or ankle boots for a complete look.
Avoid: Overly busy patterns that can clash with the leopard print.

12. White Sweater + White Midi Skirt + Nude Boots

Instagram: @theindiaedit

This monochromatic look is a winter dream! The white turtleneck sweater paired with a satin slip skirt creates a sleek and elegant silhouette.

The nude boots elongate the legs, making this outfit perfect for holiday parties or upscale gatherings.

Where to Wear: Great for holiday parties, upscale dinners, or date nights.
Pair With: A clutch for evening events or delicate jewelry for a refined touch.
Avoid: Dark accessories that can clash with the light palette.

13. Gray Turtleneck Sweater + Pleated Mini Skirt + Knee-High Boots

Instagram: @taliacupcake

A chic gray turtleneck sweater paired with a pleated mini skirt and knee-high boots creates a preppy and stylish look.

Where to Wear: Suitable for casual outings, coffee dates, or school events.
Pair With: A small crossbody bag for a youthful touch or hoop earrings for a bit of sparkle.
Avoid: Overly formal accessories that can disrupt the casual charm.

14. Black Blazer + White Pencil Skirt + Black Boots

Instagram: @selkolas

This outfit exudes confidence and professionalism! The black blazer over a white pencil skirt is a classic combination that works wonders in the office or at networking events.

The pointy toe black boots add a modern twist, making it suitable for both business and after-work gatherings.

Where to Wear: Perfect for the office, business meetings, or networking events.
Pair With: A structured tote for work or bold lipstick for evening events.
Avoid: Casual footwear like flats or sneakers.

15. White Fleece + White Skirt + Brown Boots

Instagram: @gabrielest_

This cozy outfit is perfect for chilly days! The white fleece jacket paired with a frill mini skirt creates a fun and flirty look.

The brown knee-high boots add warmth and style, making it a great choice for winter outings.

I love how this outfit balances comfort with a touch of femininity, making it perfect for casual gatherings or outdoor adventures.

Where to Wear: Great for casual outings, winter walks, or coffee dates.
Pair With: A beanie for a cozy touch or a crossbody bag for practicality.
Avoid: Heavy layers that can make the outfit look bulky.

16. Black Blazer + Gold Pleated Skirt + Slingbacks

Instagram: @elle_ferguson

This outfit is a showstopper! The black oversized blazer paired with a gold pleated maxi skirt creates a stunning contrast that’s perfect for evening events.

The black slingbacks add elegance, making it suitable for parties or formal gatherings.

Where to Wear: Ideal for parties, formal events, or upscale dinners.
Pair With: A clutch for evening events or statement jewelry for added glamour.
Avoid: Casual accessories that can detract from the elegance.

17. Long Black Coat + Gray Sweater + Pleated Skirt + Knee-High Boots

Instagram: @kristincabat

This stylish ensemble features a long black coat layered over a gray sweater and pleated skirt, paired with knee-high boots.

It’s a perfect blend of warmth and sophistication for cooler days.

Where to Wear: Ideal for city strolls, coffee dates, or casual gatherings.
Pair With: A sleek black handbag for a polished look or sunglasses for a touch of glamour.
Avoid: Bright colors that might clash with the monochrome palette.

Winter doesn’t have to mean sacrificing style for comfort. With these chic winter skirt outfits, you can embrace the season while looking fabulous.

So, step out of your comfort zone and try these combinations this winter—you’ll be amazed at how good it feels to dress up!